- Structural, spectral, optical and antimicrobial properties of synthesized 1-benzoyl-3-furan-2-ylmethyl-thiourea
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The 1-benzoyl-3-furan-2-ylmethyl-thiourea (bftu) was synthesized and its structure was determined by elemental analyses, IR spectroscopy, 1H and 13C NMR spectroscopy and single crystal X-ray diffraction analysis. Also its antimicrobi
- Karipcin, Fatma,Atis, Murat,Sariboga, Bahtiyar,Celik, Hasan,Tas, Murat
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- Synthesis, X-ray crystal structure elucidation and Hirshfeld surface analysis ofN-((4-(1H-benzo[d]imidazole-2-yl)phenyl)carbamothioyl)benzamide: Investigations for elastase inhibition, antioxidant and DNA binding potentials for biological applications
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The interest in the present study pertains to the development of a new compound based upon a benzimidazole thiourea moiety that has unique properties related to elastase inhibition, free radical scavenging activity and its DNA binding ability. The title compound,N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-3-benzoyl thiourea (C21H18N4O2SH2O:TUBC), was synthesized by reacting an acid chloride of benzoic acid with potassium thiocyanate (KSCN) along with the subsequent addition of 4-(1H-benzo[d]imidazol-2-yl)benzenamineviaa one-pot three-step procedure. The structure of the resulting benzimidazole based thiourea was confirmed by spectroscopic techniques including FTIR,1H-NMR,13C-NMR and single crystal X-ray diffraction and further examined by Hirshfeld surface analysis. TUBC was also investigated by using bothin silicomethodology including molecular docking for elastase inhibition along with quantum chemical studies andin vitroexperimental methodology utilizing elastase inhibition and free radical scavenging assay along with DNA binding experiments. Docking results confirmed that TUBC binding was within the active region of elastase. In comparison to the reference drug oleanolic acid, the low IC50value of TUBC also indicated its high tendency towards elastase inhibition. TUBC scavenged 80% of DPPH˙ radicals which pointed towards its promising antioxidant activity. TUBC-DNA binding by DFT, docking, UV-visible spectroscopy and viscosity measurements revealed TUBC to be a potential drug candidate that binds spontaneously and reversibly with DNAviaa mixed binding mode. All theoretical and experimental findings pointed to TUBC as a potential candidate for a variety of biological applications.
- Abbas, Qamar,Ahmed, Ashfaq,Arshad, Nasima,Ashraf, Saba,Channar, Pervaiz Ali,Farooqi, Shahid I.,Hokelek, Tuncer,Jasinski, Jerry P.,Kaur, Manpreet,Perveen, Fouzia,Rafiq, Mamoona,Saeed, Aamer,Ujan, Rabail
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- Syntheses based on 3,4-dimethyl-2-thioxothiazoline-5-carboxylic acid hydrazide and azide
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Treatment of 3,4-dimethyl-2-thioxothiazoline-5-carboxylic acid hydrazide with NH4SCN and PhCONCS gave the corresponding thiosemicarbazides, arylsulfochlorides yielded the arylsulfonylhydrazides, and diazotization conditions gave the correspondi
- Dovlatyan,Eliazyan,Pivazyan,Yengoyan
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- Synthesis and structural X-ray analysis of 1,1'-(naphthalene-1,8-diyl)-3, 3'-dibenzoyl-bisthiourea and its use as anion-binding receptor
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A novel artificial receptor, 1,1'-(naphthalene-1,8-diyl)-3,3'-dibenzoyl- bisthiourea, based on a 1,8-naphthalene skeleton bearing bisthiourea groups was prepared and characterized by IR and 1H-NMR, 13C-NMR, and MS spectroscopic techn
- Aydin, Fatma,Tunoglu, Nazan,Aykac, Dogan,Arslan, Nahide Burcu,Kazak, Canan
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- Synthesis, spectral and single-crystal analyses of new derivatives of 4-amino-N-benzylpiperidine
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Two new compounds of thiourea derivatives of cinnamoyl and benzoylisothiocyanate with 4-amino-N-benzylpiperidine have been successfully synthesized. The new molecules, 1-(1-benzylpiperidine-4-yl)-3-benzoyl thiourea (I) (yield 83 %) and 1-(1-benzylpiperidi
- Hassan, Ibrahim N.,Tarawneh, Mou'ad A.,Yamin, Bohari M.
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- HETEROADAMANTANES AND THEIR DERIVATIVES. 21. SYNTHESIS OF THIOUREAS OF THE 3,6-DIAZAHOMOADAMANTANE SERIES
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Unsubstituted and phenyl-substituted thioureas were obtained by the action of benzoyl isothiocyanate and phenyl isothiocyanate on amino-substituted diazahomoadamantanes.
- Kuznetsov, A. I.,Serova, T. M.,Vladimirova, I. A.,Barri, U.,Ngi, Chan,Moskovkin, A. S.
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- Design, synthesis, and anticancer activity of novel 4-thiazolidinone-phenylaminopyrimidine hybrids
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Abstract: 4-Thiazolidinones and phenylaminopyrimidines are known as anticancer agents. Imatinib is the pioneer phenylaminopyrimidine derivative kinase inhibitor, which is used for the treatment of chronic myeloid leukemia. With a hybrid approach, a novel series of 5-benzylidene-2-arylimino-4-thiazolidinone derivatives containing phenylaminopyrimidine core were designed, synthesized, and tested for their anticancer activity on K562 (chronic myeloid leukemia), PC3 (prostat cancer), and SHSY-5Y (neuroblastoma) cells. Since superior anticancer activity was observed on K562 cells, further biological studies of selected compounds (8, 15, and 34) were performed on K562 cells. For the synthesis of designed compounds, thiourea compounds were converted to 2-imino-1,3-thiazolidin-4-ones with α-chloroacetic acid in the presence of sodium acetate. 5-Benzylidene-2-imino-1,3-thiazolidin-4-one derivatives were obtained by Knoevenagel condensation of 2-imino-1,3-thiazolidin-4-ones with related aldehydes. Compounds 8, 15, and 34 were evaluated for cell viability, apoptosis studies, cell cycle experiments, and DNA damage assays. IC50 values of compounds 8, 15, and 34 were found as 5.26 ± 1.03, 3.52 ± 0.91, and 8.16 ± 1.27?μM, respectively, in K562 cells. Preferably, these compounds showed less toxicity towards L929 cells compared to imatinib. Furthermore, compounds 8 and 15 significantly induced early and late apoptosis in a time-dependent manner. Compounds 15 and 34 induced cell cycle arrest at G0/G1 phase and compound 8 caused cell cycle arrest at G2/M phase. Based on DNA damage assay, compounds 8 and 15 were found to be more genotoxic than imatinib towards K562 cells. To put more molecular insight, possible Abl inhibition mechanisms of most active compounds were predicted by molecular docking studies. In conclusion, a novel series of 5-benzylidene-2-arylimino-4-thiazolidinone derivatives and their promising anticancer activities were reported herein. Graphic abstract: [Figure not available: see fulltext.]
- Türe, Asl?,Ergül, Mustafa,Ergül, Merve,Altun, Ahmet,Kü?ükgüzel, ?lkay
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- Hepatitis C virus serine protease: Synthesis of radioactive and stable isotope-labeled potent inhibitors
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Drug candidates labeled with radioactive and stable isotopes are required for absorption, distribution, metabolism, and excretion (ADME) studies, pharmacokinetics, autoradiography, bioanalytical, and other research activities. The findings from these stud
- Latli, Bachir,Hrapchak, Matt,Gorys, Vida,Llinas-Brunet, Montse,Campbell, Scot S.,Song, Jinhua,Senanayake, Chris H.
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- Antihyperglycemic activity of chalcone based novel 1-{3-[3-(substituted phenyl) prop-2-enoyl] phenyl} thioureas
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The present study describes the synthesis of novel chalcone based 1-{3-[3-(substituted phenyl) prop-2-enoyl] phenyl} thioureas (4a-c) using Claisen Schmidt condensation and investigates their protective role in diabetic conditions and associated oxidative
- Acharjee, Satarupa,Maity, Tapan Kumar,Samanta, Subir,Mana, Supriya,Chakraborty, Tania,Singha, Tanushree,Mondal, Arijit
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- Characterization and Computational Studies of 2-(Benzamido)Thiazol-5-yl Benzoate
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2-(Benzamido)thiazolylbenzoate is synthesized via a novel method. It is characterized by spectroscopy, micranalysis, and GC-MS. It crystallizes in the monoclinic space group P21/n with a = 19.8990(5), b = 7.3680(2), c = 22.3845(6) ?, β = 113.799(1)°, V = 3002.85(14) ?3Z = 8. The HOMO-LUMO of the reactants and products are considered.
- Odame,Hosten,Betz,Lobb,Tshentu
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- Synthesis of deuterium-, tritium-, and carbon-14-labeled BILN2061, a potent hepatitis C virus protease inhibitor
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Hepatitis C virus (HCV) serine protease is a target for antiviral therapy against HCV infection, a leading cause of liver transplantation in the US. BILN2061, (1S, 4R, 65, 7Z, 145, 18A)-14-cyclopentyloxycarbonylamino-18-[2-(2- isopropylamino-thiazol-4-yl)
- Latli, Bachir,Hrapchak, Matt,Gorys, Vida,Busacca, Carl A.,Senanayake, Chris
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- The synthesis of triazolothiadiazines and thiadiazoles from 1,2-bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-ethanol and ethane
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The reaction of DL-malic and succinic acids with thiocarbohydrazide afforded 1,2-bis[4-amino-5-mercapto-1,2,4-triazol-3-yl]-ethane derivatives 3a and 3b. The reaction of 3a,b with phenacyl bromide and benzoin afforded 1,2-bis-1,2,4-triazolo [3,4-b][1,3,4]thiadiazine derivatives 4 and 5. The carboethoxymethylation of 3a and 3b gave 6a and 6b, respectively, and their reactions with carbon disulfide and benzoylisothiocyanate gave the 1,2-bis-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole 7 and 9, and with p-nitrobenzaldehyde gave a Schiff's base and dihydrothiadiazole 8. The structures were confirmed by using 1H and 13C NMR spectra. Selected members of these compounds were screened for antimicrobial activity. Copyright Taylor & Francis Group, LLC.
- Moustafa,Haggam,Younes,El Ashry
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- Theoretical studies of molecular structure and vibrational spectra of O-ethyl benzoylthiocarbamate
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O-Ethyl benzoylthiocarbamate has been synthesized and characterized by elemental analysis and FT-IR. The crystal structure was determined by X-ray diffraction analysis. Title compound crystallizes in the orthorhombic space group Pna21, with Z =
- Arslan, Hakan,Floerke, Ulrich,Kuelcue, Nevzat
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- Synthesis and intramolecular cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea
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The reaction of 3-amino-4,6-dimethylpyridin-2(1H)-one and 3-amino-4-phenylpyridin-2-one with acyl isothiocyanates (benzoyl-, 4-bromobenzoyl-, and methacryloyl isothiocyanates) and with allyl isothiocyanate has been studied. The N-carbamothioyl methacrylam
- Kulakov,Nikitina,Fisyuk,Goncharov,Shul'Gau,Gulyaev
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- Synthesis and characterization of copper(I) halide complexes with N-(2, 6-diisopropylphenyl)-N′-benzoylthiourea: Monomeric, dimeric, and cage structures
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The N-(2, 6-diisopropylphenyl)-N′-benzoylthiourea ligand (shown as L) (1) was synthesized and characterized. Reactions of 1 with CuCl2 and CuBr2 afforded the monomeric L2CuCl (2) and dimeric [LBrCu(μ-L)]2 (3), r
- Zhao, Xiao-Ya,Zhu, Cheng-Ben,Li, Hai-Pu,Yang, Ying,Roesky, Herbert W.
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- Gold(I), silver(I) and copper(I) complexes of 2,4,6-trimethylphenyl-3-benzoylthiourea; synthesis and biological applications
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2,4,6-Trimethylphenyl-3-benzoylthiourea (L) and its gold(I), silver(I) and copper(I) complexes were synthesized. Treatment of L with HAuCl4, AgNO3 and CuI in CH3CN afforded complexes of general representation, M(L)X, where
- Khan, Umar Ali,Badshah, Amin,Tahir, Muhammad Nawaz,Khan, Ezzat
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- N-Benzoyl-S-(undecyl)-dithiocarbamate: Synthesis, characterization, X-ray single crystal structure, thermal behavior and computational studies
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A new dithiocarbamate molecule, named as N-benzoyl-S-(undecyl)-dithiocarbamate (C19H29NOS2), was synthesized and characterized by 1HNMR, 13CNMR, FT-IR spectroscopic methods. X-ray analysis of the crystal structure of title compound showed the presence of triclinic space group with a = 4.2417 (8) ?, b = 20.010 (4) ?, c = 27.959 (6) ?, Z = 4, V = 2338.9 ?3. Detailed investigation of molecular packing of the molecule indicated the presence of intermolecular hydrogen bond between C1–H1?S4i and C24–H24?S2v that generates R2 2 (10) motifs, and intermolecular hydrogen bonds between N1–H111?S4ii and N2–H222?S2iv atoms that forms R2 2 (7) rings. Thermal properties of the title compound were investigated by thermogravimetric analysis (DTA/TG) and differential scanning calorimetry (DSC). Molecular electrostatic potential (MEP), the HOMO and LUMO energies and thermodynamic parameters of the title compound were calculated using density functional theory (DFT) with B3LYP/6-311G (d,p) level.
- Ayd?n, Fatma,Arslan, N. Burcu,Aslan, Kadir
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- Guanidinyl benzothiazole derivatives: Synthesis and structure activity relationship studies of a novel series of potential antimicrobial and antioxidants
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Abstract: A series of N-phenyl-substituted and disubstituted guanidinyl benzothiazole derivatives 4a–4m were synthesized and characterized as novel antimicrobial and antioxidant agents. The in-vitro antioxidant activities of these compounds were evaluated and compared with commercial antioxidants, using ascorbic acid (AA) and employing 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay and 2,2′-azino-bis (3-ethylbenzthiazoline-6-sulphonic acid (ABTS) assay. The results showed that IC50 values of compounds 4a and 4m were similar to the IC50 values of the standard. This assay indicates the good activities of these compounds. In addition, the in-vitro antimicrobial activities of these compounds were evaluated and the results demonstrated that the compounds 4i and 4l exhibited excellent antimicrobial activities. Compounds 4c and 4i having electron withdrawing groups at p-position and compound 4l and 4m having electron donating groups at o-position showed better antimicrobial activities compared to the standard. Graphical Abstract: [Figure not available: see fulltext.]
- Bhat, Mahesh,Belagali
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- Phthalazinone in heterocyclic synthesis: Synthesis of some s-triazole, s-triazolothiadiazine, s-triazolothiadiazine, and s-triazolothiadiazole derivatives as pharmaceutical interest
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1(2H)-Oxophthalazine-2-acetic acid ethyl ester was allowed to react with various reagents under different conditions to yield compounds 2-[(4-substituted-5-mercaptotriazol-3-yl) methyl]-1(2H)-oxophthalzines 5 and 7 which acted as starting materials for the preparation of some new s-triazolo[5,1-b][1,3]thiazine (8), s-triazolo[3,4-b][1,3,4]thiadiazine 9,12,14,20, and s-triazolo[3,4-b][1,3,4]thiadiazole 18,21 derivatives.
- Hassanien, Abu Zeid Abd El-Baset
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- DNA binding, DNA cleavage and HSA interaction of several metal complexes containing N-(2-hydroxyethyl)-N′-benzoylthiourea and 1,10-phenanthroline ligands
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Abstract: Four novel ternary metal complexes of the type [M(Phen)(L1)2)] [phen?=?1,10-phenanthroline, L1?=?N-(2-hydroxyethyl)-N′-benzoylthiourea, M?=?Ni(II)(1), Co(II) (2), Cu(II) (3), Pd(II) (4)] were synthesized. The org
- Peng, Bo,Gao, Zhuantao,Li, Xibo,Li, Tingting,Chen, Guorong,Zhou, Min,Zhang, Ji
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- Recognition of anions and monocarboxylic acids by a fluorescent guanidine-based receptor
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A guanidine-based fluorescent receptor has been synthesised to study its binding behaviour towards anions (F-, Cl-, Br-, I- and AcO-). The two donor N-H bonds of the receptor do not point in the same direction; rather, one N-H bond is intramolecularly hydrogen-bonded with the carbonyl oxygen atom. The nature of the donor-acceptor (DA) arrangement induces moderate binding properties. The binding behaviour towards monocarboxylic acids (benzoic acid and phenylacetic acid) is also compared. The binding behaviour of receptor 1 towards the F- anion is higher among the anions studied, whereas in the case of monocarboxylic acid, the binding constant with phenylacetic acid is higher than benzoic acid.
- Goswami, Shyamaprosad,Jana, Subrata,Chakrabarty, Rinku,Fun, Hoong-Kun
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- Synthesis of acyl thiourea derivatives of chitosan and their antimicrobial activities in vitro
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Three different acyl thiourea derivatives of chitosan (CS) were synthesized and their structures were characterized by FT-IR spectroscopy and elemental analysis. The antimicrobial behaviors of CS and its derivatives against four species of bacteria (Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Sarcina) and four crop-threatening pathogenic fungi (Alternaria solani, Fusarium oxysporum f. sp. vasinfectum, Colletotrichum gloeosporioides (Penz.) Saec, and Phyllisticta zingiberi) were investigated. The results indicated that the antimicrobial activities of the acyl thiourea derivatives are much better than that of the parent CS. The minimum value of MIC and MBC of the derivatives against E. coli was 15.62 and 62.49 μg/mL, respectively. All of the acyl thiourea derivatives had a significant inhibitory effect on the fungi in concentrations of 50-500 μg/mL; the maximum inhibitory index was 66.67%. The antifungal activities of the chloracetyl thiourea derivatives of CS are noticeably higher than the acetyl and benzoyl thiourea derivatives. The degree of grafting of the acyl thiourea group in the derivatives was related to antifungal activity; higher substitution resulted in stronger antifungal activity.
- Zhong, Zhimei,Xing, Ronge,Liu, Song,Wang, Lin,Cai, Shengbao,Li, Pengcheng
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- Synthesis, supramolecular structure, antimicrobial and plant-growth regulation activities of n-benzoylthiourea
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N-Benzoylthiourea has been synthesized and characterized by elemental analysis, IR and 1H NMR etc. The X-ray crystallography of the compound indicates that the carbonyl group forms an intramolecular hydrogen bond with the N2-H2 group, which forms a six-membered ring (C7/N1/C8/N2/H2/O1) srtucture. Each molecule are linked by the intermolecular N2-H2A...S2 and N4-H4A...S1 hydrogen bonds to form a dimer, adjacent dimers are linked by the intermolecular N1-H1N...S2 and N3-H3N...S1 hydrogen bonds, leading to a hydrogenbonded netty structure. The results indicated that the N-benzoylthiourea played the important role in plant-growth regulators and may be a potential source of active antimicrobial agents.
- Zhao, Meng-Meng,Dong, Xiu-Yan,Yang, U-Hua,Li, Gang,Zhang, U-Jie
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- 1-Benzoyl-3-[(2-benzylsulfanyl)phenyl]thiourea
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In the title compound, C21H18N2OS2, a strong intramolecular N-H?O hydrogen bond [N?O = 2.642(3)?] between the amide N atom and the benzoyl O atom forms an almost planar six-membered ring in the central part of the molecule. In the crystal, molecules are p
- Bhattacharjee, Tirtha,Gogoi, Prasanta,Puranik, Vedavati G.,Gawade, Rupesh L.,Barman, Pranjit
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- SYNTHESIS, CHARACTERIZATION, AND COMPUTATIONAL STUDIES OF N-[(9E)-8,10,17-TRIAZATETRACYCLO[8.7.0.02,7.011,16]HEPTADECA- 1(17),2,4,6,11(16),12,14-HEPTAEN-9-YLIDENE]BENZAMIDE
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Abstract: N-[(9E)-8,10,17-Triazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(17),2,4,6,11(16),12,14-heptaen-9-ylidene] benzamide (I) is synthesized and characterized by spectroscopy, microanalysis, and single crystal X-ray diffractometry. Compound I crystallizes in the monoclinic space group P21/c with a = 15.8980(7) ?, b = 4.8067(2) ?, c = 21.0455(10) ?, β = 101.153(2)°, and Z = 4. The experimental bond lengths and bond angles are contrasted with computed bond lengths and bond angles.
- Hosten, E. C.,Odame, F.,Tshentu, Z. R.
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- Cu(II)-N-benzyl-amino-1H-tetrazole complex immobilized on magnetic chitosan as a highly effective nanocatalyst for C-N coupling reactions
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Herein, the synthesis of a novel catalytic nanosystem with high activity and easy recoverability through immobilization of Cu(II)-N-benzyl-amino-1H-tetrazole complex on magnetic chitosan (MCS-BAT-Cu(II)) is reported. The catalytic potential of MCS-BAT-Cu(II) catalyst has been assessed in C-N coupling reaction of 5-amino-1H-tetrazole with aryl halides. Various aryl iodides/bromides were successfully coupled using MCS-BAT-Cu(II) catalyst for the synthesis of 1-aryl-5-amino-1H-tetrazoles with excellent reaction yields. In addition, the magnetic catalyst was easily and effectively separated from the reaction mixture using an external magnet and reused five times without notable loss of catalytic activity.
- Ghafuri, Hossein,Nasrollahzadeh, Mahmoud,Sajjadi, Mohaddeseh
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- Efficient Synthesis of Benzothiazinone Analogues with Activity against Intracellular Mycobacterium tuberculosis
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8-Nitrobenzothiazinones (BTZs) are a promising class of antimycobacterial agents currently under investigation in clinical trials. Starting from thiourea derivatives, a new synthetic pathway to BTZs was established. It allows the formation of the thiazinone ring system in one synthetic step and is applicable for preparation of a wide variety of BTZ analogues. The synthetic procedure furthermore facilitates the replacement of the sulphur atom in the thiazinone ring system by oxygen or nitrogen to afford the analogous benzoxazinone and quinazolinone systems. 36 BTZ analogues were prepared and tested in luminescence-based assays for in vitro activity against Mycobacterium tuberculosis (Mtb) using the microdilution broth method and a high-throughput macrophage infection assay.
- Av-Gay, Yossef,Imming, Peter,Narula, Gagandeep,Richter, Adrian,Rudolph, Ines,Wagner, Christoph,Seidel, Rüdiger W.
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supporting information
(2021/12/27)
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- Synthesis and evaluation of the anticancer activity of [Pt(diimine)(N,N-dibutyl-N′-acylthiourea)]+complexes
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Despite the concerted efforts to develop targeted cancer treatments, these therapies are plagued by the rapid development of resistance and serious adverse drug reactions. Based on the wide clinical use and successes of the platinum drugs like cisplatin and oxaliplatin, we investigated the synthesis and potential anticancer efficacy of alternative platinum complexes. A series of nine cationic square planar platinum(ii) complexes were synthesized and characterized and then evaluated for their anticancer activity. The complexes were of the type [Pt(diimine)(Ln-κO,S)]+where diimine is either 1,10-phenanthroline (phen), 5,6-dimethyl-1,10-phenanthroline (dmp) or dipyrido[3,2-f:2′,3′-h]quinoxaline (dpq) and Ln-κO,Srepresenting variousN,N-dibutyl-N′-acylthiourea ligands. The anticancer activity of the synthesised complexes was evaluated against two lung cancer cell lines (A549 and H1975) and a colorectal cancer cell line, HT-29. The 50% inhibitory concentrations (IC50) for the most cytotoxic compounds were determined and the mode of cell death evaluated. The structure-activity relationships indicated that complexes with the 5,6-dimethyl-1,10-phenanthroline variation of the diimine ligand were the most active against the cell lines tested, while the activity of complexes based on the acylthiourea ligand varied between the cell lines. IC50values for the three active platinum complexes were in the low micromolar range for the three cell lines and ranged between 0.68 μM and 2.28 μM. Changes to cell morphology indicate that the active platinum complexes induce cell death by both apoptosis and paraptosis. The complexes were able to induce the nuclear expression of the cyclin-dependent kinase inhibitor, p21, which is an indicator of DNA damage. The collective data indicate that these platinum complexes are valuable lead compounds for further analysis and cancer drug discovery.
- Harmse, Leonie,Kotzé, Izak A.,Magwaza, Rachael N.,Peega, Tebogo
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p. 11742 - 11762
(2021/09/06)
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- Mononuclear copper(i) complexes of triphenylphosphine and: N, N ′-disubstituted thioureas as potential DNA binding chemotherapeutics
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In this work, nine new mixed-ligand complexes with the general formula [CuBr(TPP)2Tu1-9] were synthesized. The copper(i) complexes of triphenylphosphine (TPP) and different N,N′-disubstituted thioureas (Tu) were characterized via spectroscopic techniques including Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (1H, 13C, and 31P NMR), and single-crystal X-ray diffraction (SC-XRD). The complexes were synthesized via the direct reaction of bromo(tris(triphenylphosphine)copper(i)) [BrCu(PPh3)3] precursor and thiourea ligand solution under ambient conditions. Complexes 1, 2 and 3 crystallized in a triclinic system with the P1 space group. Each complex is mononuclear, and the copper atom is tetrahedrally attached to two TPP groups through the phosphorous atom, one thiourea molecule through the sulfur atom and one bromine atom. The synthesized compounds were docked with a DNA macromolecule to predict their binding site and it was found that all molecules showed favorable binding to the DNA minor grooves. The DNA interaction studies of the representative complexes demonstrated their efficient DNA binding affinities. Based on the docking and DNA interaction results, complex 7 was found to be the best binder with a docking affinity of 382.2 kJ mol-1 and binding constant of 3.96 × 104 M-1. This compound tends to interact with the minor groove through the bromine atom positioning the side triphenylphosphine rings along the X-axis of the groove while keeping the 1-(2-chlorobenzyl)-3-(3-(trifluoromethyl)phenyl)thiourea ring on the outside.
- Khan, Syed Ishtiaq,Ahmad, Sajjad,Khan, Inayat Ali,Badshah, Amin,Rauf, Muhammad Khawar,Putejo, Jahangir Ali,Siddiq, Muhammad Nasir,Kausar, Samia,Altaf, Ataf Ali
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p. 8925 - 8935
(2021/06/01)
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- Theoretical and experimental verification of molecular properties of novel benzamide derivatives using computational platforms and in vitro antibacterial activity
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A series of N-(benzo[d]oxazol-2-ylcarbamothioyl)-2/4-substituted benzamides were synthesized by the reaction of 2-aminobenzoxazole with apposite benzoyl isothiocyanate. The structure of the newly synthesized compounds was confirmed by chemical tests, elemental (C, H, N, and S), and spectral (IR, 1H NMR, 13C NMR, and mass) analysis. All the synthesized compounds were evaluated experimentally for their antibacterial activity against Gram-positive and Gram-negative bacteria. The test results show moderate to potent antibacterial activity compared to the standard drug. The binding interactions of newly synthesized ligand and protein were correlated using a molecular docking study using a binding pocket of GlcN-6-P synthase. [Figure not available: see fulltext.].
- Wanjari, Poonam M.,Mokale, Santosh N.,Bharati, Avinash V.,Ingle, Vishwas N.
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p. 655 - 663
(2021/01/07)
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- Synthesis and Investigation of the Antibacterial Activity of New Tris-Thiourea Derivatives
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An efficient procedure for the preparation of symmetrical tris-thiourea derivatives (5a – 5h) by means of one-pot condensation reaction between available benzoyl chlorides (1a –1h) with potassium thiocyanate (2) and melamine (4) under reflux conditions is
- Ghorbani, Saghi Shiroud,Montazeri, Naser,Zeydi, Masoud Mohammadi,Ghane, Masood
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- Synthesis of Novel Tris-1,2,4-triazole Derivatives and Their Antibacterial Activity
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Abstract: A series of novel 3,3′,3″-[1,3,5-triazine-2,4,6-triyltris(azanediyl)]tris(5-aryl-1H-1,2,4-triazole-1-carbothioamide) derivatives were designed and synthesized through reaction of new tris-thiourea derivatives with thiosemicarbazide and sodium hy
- Ghane, M.,Ghorbani, S. Shiroud,Montazeri, N.,Zeydi, M. M.
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p. 605 - 610
(2021/06/02)
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- Electrochemical sensing of doxepin using acylthiourea-modified glassy carbon electrode
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Acylthiourea (ATU) compounds 4-(3-(furan-2-carbonyl)thioureido)benzoic acid (1), 4-(3-(thiophene-2-carbonyl)thioureido)benzoic acid (2), and 4-(3-(benzoyl)thioureido)benzoic acid (3) were synthesized and characterized by NMR (1H and 13/su
- Bhuvanesh, N. S. P.,Biju, V. M.,Kalaiyarasi, A.,Karvembu, R.
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- Synthesis and antituberculosis activity of new acylthiosemicarbazides designed by structural modification
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Acylthiosemicarbazides 8a–n were designed by structural modification of lead Compound 7. The syntheses of 8a–n involve a five-step procedure starting from carboxylic acids. Compounds 8a–n were tested against three Mycobacterium tuberculosis strains to measure their inhibitory antituberculosis activities. These activities could be explained according to the presence or absence of the chlorine substituent in the aromatic ring of the amide joined to the thiosemicarbazide core. Thiosemicarbazide derivative 8n is a candidate for the development of novel antitubercular agents. Ongoing studies are focused on exploring the mechanism by which these compounds inhibit M. tuberculosis cell growth.
- Martínez, Roberto,Espitia-Pinzón, Clara I.,Silva Miranda, Mayra,Chávez-Santos, Rosa María,Pretelin-Castillo, Gustavo,Ramos-Orea, Aldahir,Hernández-Báez, ángela M.,Cotlame-Pérez, Sandra,Pedraza-Rodríguez, Rogelio
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p. 350 - 355
(2019/12/03)
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- Novel N-Acyl-1H-imidazole-1-carbothioamides: Design, Synthesis, Biological and Computational Studies
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The present study reports the convenient synthesis, spectroscopic characterization, bio-assays and computational evaluation of a novel series of N-acyl-1H-imidazole-1-carbothioamides. The screened derivatives displayed excellent antioxidant activity, moderate antibacterial and antifungal potential. The screened derivatives were found to be highly biocompatible against hRBCs. Molecular docking ascertained the mechanism and mode of action towards the molecular target delineating that ligands and complexes were stabilized at the active site by electrostatic and hydrophobic forces in accordance to the corresponding experimental results. Docking simulation provided additional information about the possibilities of inhibitory potential of the compounds against RNA. Computational evaluation predicted that N-acyl-1H-imidazole-1-carbothioamides 5c and 5g can serve as potential surrogates for hit to lead generation and design of novel antioxidant and antibacterial agents.
- Aziz, Hamid,Saeed, Aamer,Khan, Muhammad Aslam,Afridi, Shakeeb,Jabeen, Farukh,Ashfaq-ur-Rehman,Hashim, Muhammad
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- Substituted 4-phenylthiazoles: Development of potent and selective A1, A3 and dual A1/A3 adenosine receptor antagonists
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Adenosine acts as a powerful signaling molecule via four distinct G protein-coupled receptors, designated A1, A2A, A2B and A3 adenosine receptors (ARs). A2A and A2B ARs are Gs-coupled, while A1 and A3 ARs inhibit cAMP production via Gi proteins. Antagonists for A1 and A3 ARs may be useful for the treatment of (neuro)inflammatory diseases including acute kidney injury and kidney failure, pulmonary diseases, and Alzheimer's disease. In the present study, we optimized the versatile 2-amino-4-phenylthiazole scaffold by introducing substituents at N2 and C5 to obtain A1 and A3 AR antagonists including dual-target compounds. Selective A1 antagonists with (sub)nanomolar potency were produced, e.g. 11 and 13. These compounds showed species differences being significantly more potent at the rat as compared to the human A1 AR, and were characterized as inverse agonists. Several potent and selective A3 AR antagonists, e.g. 7, 8, 17 and 22 (Ki values of 5–9 nM at the human A3 AR) were prepared, which were much less potent at the rat orthologue. Moreover, dual A1/A3 antagonists (10, 18) were developed showing Ki values between 8 and 42 nM. Docking and molecule dynamic simulation studies using the crystal structure of the A1 AR and a homology model of the A3 AR were performed to rationalize the observed structure-activity relationships.
- Abdelrahman, Aliaa,Yerande, Swapnil G.,Namasivayam, Vigneshwaran,Klapschinski, Tim A.,Alnouri, Mohamad Wessam,El-Tayeb, Ali,Müller, Christa E.
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supporting information
(2019/12/24)
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- Doramectin structural derivative and synthesis method thereof
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The invention belongs to the field of compound synthesis, and particularly relates to a Doramectin structural derivative and a synthesis method thereof. The novel Doramectin structural derivative adopts the specific technical scheme that the invention provides a series of novel Doramectin structural derivatives. Compared with a conventional chemical pesticide, the Doramectin structural derivativehas the advantages of being higher in efficiency, low in toxin, environmentally friendly, higher in applicability and the like, and is hopeful to become a new-generation green environment-friendly biological pesticide, wherein an acyl urea compound in which R is 2,6-difluorophenyl has favorable diamond-back moth resisting activity; an acyl urea compound in which R is C3H5 has favorable corn borerresisting activity; and an acyl thiourea homologues compound in which R is 2,6-difluorophenyl has favorable mythimna separata resisting activity.
- -
-
Paragraph 0080; 0085
(2020/03/03)
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- Triton-B catalyzed one pot multicomponent synthesis of isothiocyanates in non-aqueous medium
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A facile and novel method to synthesize isothiocyanides from cyclic and acyclic amines and carbon disulphide in DMSO with Triton-B as catalyst in non-aqueous medium is being reported. The method is less tedious and offers excellent yields. The structures have been elucidated by 1H NMR, 13C NMR and mass spectroscopy.
- Singh, Neha,Khare, Richa
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p. 1636 - 1638
(2019/06/11)
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- Copper promoted C-S and C-N cross-coupling Reactions:The synthesis of 2-(N-Aryolamino)benzothiazoles and 2-(N-Aryolamino)benzimidazoles
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The synthesis of 2-(N-aryolamino)benzothiazoles and 2-(N-aryolamino)benzimidazoles has been accomplished in the presence of copper catalyst. These reactions involve C-S and C-N cross-coupling reaction. All electron donating and withdrawing substituent's readily underwent the reaction to give target products in good to excellent yield. In addition, the reaction also gave target product in high yield with bulk scale.
- Shaik, Baji vali,Seelam, Mohan,Tamminana, Ramana,Kammela, Prasad Rao
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p. 3865 - 3874
(2019/06/20)
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- Synthesis, characterization and catalytic performance of Pd(II) complex immobilized on Fe3O4@SiO2 nanoparticles for the ligand-free cyanation of aryl halides using K4Fe(CN)6
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This work shows the preparation of a novel magnetic catalyst via immobilization of Pd(II)-N-benzyl-N-(4-bromophenyl)-5-amino-1H-tetrazole complex on the Fe3O4@SiO2 nanoparticles (NPs). The application of Fe3O4@SiO2 NPs supported Pd(II)-N-benzyl-N-(4-bromophenyl)-5-amino-1H-tetrazole complex [Fe3O4@SiO2-BAT-Pd(II)] nanocatalyst is described for the cyanation of aryl iodides and bromides to the corresponding aryl nitriles using potassium hexacyanoferrate(II) [K4Fe(CN)6] as a non-toxic and economic cyanating agent under ligand- and additive-free conditions. Some aryl nitriles were efficiently synthesized from the corresponding aryl bromides and iodides in the presence of Fe3O4@SiO2-BAT-Pd(II) nanocomplex. The core-shell nanocomplex demonstrated the superior catalytic performance for the synthesis of synthetically valuable aryl nitriles within good to excellent yields. This process eliminates the need to handle highly toxic metal cyanides, and it can be easily recovered and reused for six consecutive runs with no decreasing of its catalytic capability. Highlights: Preparation of Pd(II) complex immobilized on Fe3O4@SiO2 nanoparticles [Fe3O4@SiO2-BAT-Pd(II) nanocomplex]. Characterization of Fe3O4@SiO2-BAT-Pd(II) nanocomplex using XRD, FT-IR, EDS, VSM, TEM and FESEM analyses. Catalytic cyanation of the various aryl halides with K4Fe(CN)6 under ligand-free conditions. The nanocomplex can be recovered and isolated six times with no significant loss of its catalytic ability.
- Nasrollahzadeh, Mahmoud,Maryami, Mahboobe,Sajjadi, Mohaddeseh,Mehdipour, Ebrahim
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- Novel acyl thiourea derivatives: Synthesis, antifungal activity, gene toxicity, drug-like and molecular docking screening
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Nine novel acyl thioureas were synthesized. Their identities and purities were confirmed by LC-MS spectra; each structure was elucidated by elemental analysis, IR, 1Н and 13C NMR spectra. Applying an in vitro screening of their antifungal potential, three substances (3, 5, and 6) could be selected as showing high activity against 11 fungi and 3 Phytophthora strains of phytopathogenic significance. Analysis of gene toxicity with the Salmonella reverse mutagenicity test, as an assessment of drug likeness, lipophilicity, and calculations of frontier molecular orbitals assign a low toxicity profile to these compounds. Molecular docking studies point to 14α-demethylase (CYP51) and N-myristoyltransferase (NMT) as possible fungal targets for growth inhibition. The findings are discussed with respect to structure–activity relationship (SAR).
- Antypenko, Lyudmyla,Meyer, Fatuma,Kholodniak, Olena,Sadykova, Zhanar,Jirásková, Tereza,Troianova, Anastasiia,Buhaiova, Vladlena,Cao, Surui,Kovalenko, Sergiy,Garbe, Leif-Alexander,Steffens, Karl G.
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- Design, computational studies, synthesis and biological evaluation of thiazole-based molecules as anticancer agents
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Background: Abolition of cancer warrants effective treatment modalities directed towards specific pathways dysregulated in tumor proliferation and survival. The antiapoptotic Bcl-2 proteins are significantly altered in several tumor types which position them as striking targets for therapeutic intervention. Here we designed, computationally evaluated, synthesized, and biologically tested structurally optimized thiazole-based small molecules as anticancer agents. Methods: The virtually designed 200 molecules were subjected to rigorous docking and in silico ADME-Toxicity studies. Out of this, 23 skeletally diverse thiazole-based molecules which passed pan assay interference compounds (PAINS) filter and were synthetically feasible were synthesized in 3 steps using cheap and readily available reagents. The molecules were in vitro evaluated against Bcl-2-Jurkat, A-431 cancerous cell lines and ARPE-19 cell lines. Molecular Dynamics (MD) simulation studies were performed to analyse conformational changes induced by ligand 32 in Bcl-2. Flow cytometry analysis of compound 32 treated Bcl-2 cells was done to check apoptosis. Results: The molecules exhibited appreciable interactions with Bcl-2 and were having acceptable drug like properties as tested in silico. The multi step synthesis yielded 23 skeletally diverse thiazole-based molecules in up to 80% yield. The molecules simultaneously inhibited Bcl-2 Jurkat cells in vitro without causing detectable toxicity to normal cells (ARPE-19 cells). Among them molecules 32, 50, 53, 57 and 59 showed considerable activities against Bcl-2 Jurkat and A-431cell lines at concentrations ranging from 32–46 μM and 34–52 μM, respectively. The standard doxorubicin exhibited IC50 in Bcl-2 Jurkat and A-431cell lines at 45.87 μM and 42.37 μM, respectively. The molecule 32, almost equipotent in both the cell lines was subjected to molecular dynamics (MD) simulation with Bcl-2 protein (4IEH). It was shown that 32 interacted with protein majorly via hydrophobic interactions and few H-bonding interactions. Fluorescence-activated cell sorting (FACS) analysis established that molecule is dragging cancerous cells towards apoptosis. Discussion and conclusion: The chemical intuition was checked by computation coupled with biological results confirmed that thiazole-based hits have the potential to be developed downstream into potent and safer leads against antiapoptotic Bcl-2 cells.
- Anuradha,Patel, Sagarkumar,Patle, Rajkumar,Parameswaran, Preethi,Jain, Alok,Shard, Amit
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- New ferrocene based thiourea and guanidines: Synthesis, Structural Elucidation, Aggregation Properties, DNA Binding Studies, and DFT calculations
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One new ferrocenyl thiourea and four new ferrocene-based alkyl guanidines have been successfully synthesized and well characterized by FT-IR, 1H and 13C NMR. Aggregation properties of ferrocene-based guanidines have been assessed by determining their critical micelles concentration through tensiometry and UV-Visible spectroscopy in the ethanol solution. The results obtained through both the techniques were in close agreement. DFT calculations were performed to calculate the charges distribution, EHOMO, ELUMO and band gaps of synthesized compounds which were further supported through UV-Visible spectroscopy. Due to the ability of ferrocene and guanidine compounds to bind with DNA, their DNA binding studies were performed through cyclic voltammetry and UV-Visible spectroscopy. Binding constant values of the guanidine derivatives are higher than the thiourea and have a linear dependence on the lipophilicity.
- Azeem, Maria,Patujo, Jahangeer Ali,Fatima, Saira,Badshah, Amin,Saleem, Laiba,Saif-Ur-Rehman
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p. 1126 - 1137
(2020/01/09)
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- Synthesis, characterization and chemosensitivity studies of half-sandwich ruthenium, rhodium and iridium complexes containing к1(S) and к2(N,S) aroylthiourea ligands
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The reaction of [(p-cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) metal precursors with aroylthiourea ligands (L1-L3) yielded a series of neutral mono-dentate complexes 1–9. The neutral mono-dentate coordination of aroylthiourea with metals via S atom was confirmed by single crystal X-ray diffraction study. Further reaction of mono-dentate complexes 1–9 with excess NaN3 in polar solvent resulted in the formation of highly strained four member ring к2(N,S) azido complexes 10–18. Further these complexes were treated with activated alkynes to isolate triazole complexes, but unfortunately the reaction was unsuccessful. All these complexes were fully characterized by various spectroscopic techniques. The molecular structures of the representative complexes have been determined by single crystal X-ray diffraction studies. The molecular structures of the complexes revealed typical piano stool geometry around the metal center. The chemosensitivity activities of the complexes 1–9 evaluated against the cancer cell line HCT-116 (human colorectal carcinoma) and ARPE-19 (human retinal epithelial cells) cell line. Of these, complex 3 was the most potent and whilst its potency was less than cisplatin, its selectivity for cancer as opposed to non-cancer cell lines in vitro was comparable to cisplatin.
- Lapasam, Agreeda,Hussain, Omar,Phillips, Roger M.,Kaminsky, Werner,Kollipara, Mohan Rao
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p. 272 - 280
(2018/11/26)
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- Design, synthesis and algicides activities of thiourea derivatives as the novel scaffold aldolase inhibitors
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By using a new Fragment-Based Virtual Screen strategy, two series of novel FBA-II inhibitors (thiourea derivatives) were de novo discovered based on the active site of fructose-1, 6-bisphosphate aldolase from Cyanobacterial (CyFBA). In comparison, most of the N-(2-benzoylhydrazine-1-carbonothioyl) benzamide derivatives (L14~L22) exhibit higher CyFBA-II inhibitory activities compared to N-(phenylcarbamothioyl) benzamide derivatives (L1~L13). Especially, compound L14 not only shows higher CyFBA-II activity (Ki = 0.65 μM), but also exhibits most potent in vivo activity against Synechocystis sp. PCC 6803 (EC50 = 0.09 ppm), higher (7-fold) than that of our previous inhibitor (EC50 = 0.6 ppm). The binding modes of compound L14 and CyFBA-II were further elucidated by jointly using DOX computational protocol, MM-PBSA and site-directed mutagenesis assays. The positive results suggest that strategy adopted in this study was promising to rapidly discovery the potent inhibitors with novel scaffolds. The satisfactory algicide activities suggest that the thiourea derivatives is very likely to be a promising lead for the development of novel specific algicides to solve Cyanobacterial harmful algal blooms (CHABs).
- Xiao, Shan,Wei, Lin,Hong, Zongqin,Rao, Li,Ren, Yanliang,Wan, Jian,Feng, Lingling
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p. 805 - 812
(2019/02/03)
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- Water soluble Ru (II)–p-cymene complexes of chiral aroylthiourea ligands derived from unprotected D/L-alanine as proficient catalysts for asymmetric transfer hydrogenation of ketones
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The newfangled chiral aroylthiourea ligands (L1-L6) were produced from unprotected D/L-alanine and their water soluble Ru (II) organometallic catalysts (1–6) were designed from their reaction with [RuCl2(η6-p-cymene)]2. The analytical and spectral methods were used to confirm the structure of the ligands and complexes. The solid state structure of L1, 5 and 6 was confirmed by single crystal XRD. The organometallic compounds (1–6) catalyzed the asymmetric transfer hydrogenation of aromatic, heteroaromatic and bulky ketones to yield respective enantiopure secondary alcohols with admirable conversions (up to 99%) and attractive enantiomeric excesses (ee up to 98%), in presence of formic acid and triethylamine in water medium under non-inert atmospheric conditions.
- Sheeba, Mani Mary,Tamizh, Manoharan Muthu,Bhuvanesh, Nattamai S.P.,Karvembu, Ramasamy
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- Supramolecular self-assembly of new thiourea derivatives directed by intermolecular hydrogen bonds and weak interactions: crystal structures and Hirshfeld surface analysis
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Abstract: We synthesized and characterized a series of four closely related thiourea derivatives (1–4) obtained by reaction of 4-R-benzoyl chloride (R: H, Cl, CH3, and OCH3) with equimolar amount of potassium thiocyanate and dibenzyl
- Gumus, Ilkay,Solmaz, Ummuhan,Binzet, Gun,Keskin, Ebru,Arslan, Birdal,Arslan, Hakan
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p. 169 - 198
(2018/09/25)
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- Chemosensing, molecular docking and antioxidant studies of 8-aminoquinoline appended acylthiourea derivatives
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Acylthiourea derivatives, 1-benzoyl-3-(quinolin-8-yl)thiourea (1), 1-(furan-2-carbonyl)-3-(quinolin-8-yl)thiourea (2) and 1-(thiophene-2-carbonyl)-3-(quinolin-8-yl)thiourea (3) were synthesized and well characterized by using NMR (1H and 1
- Kalaiyarasi,Haribabu,Gayathri,Gomathi,Bhuvanesh,Karvembu,Biju
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p. 450 - 460
(2019/03/14)
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- A useful synthesis of 2-acylamino-1,3,4-oxadiazoles from acylthiosemicarbazides using potassium iodate and the discovery of new antibacterial compounds
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A useful method for the synthesis of 2-acylamino-1,3,4-oxadiazoles was developed. By using potassium iodate as an oxidant in water at 60 ?C, a wide range of 2-acylamino-1,3,4-oxadiazoles were afforded in moderate to excellent yields within two
- Li, Tianlei,Wen, Gang,Li, Jishun,Zhang, Wenxuan,Wu, Song
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supporting information
(2019/05/02)
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- Synthesis, molecular docking and kinetic studies of novel quinolinyl based acyl thioureas as mushroom tyrosinase inhibitors and free radical scavengers
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The enzyme tyrosinase plays a vital role in melanin biosynthesis and enzymatic browning of vegetables and fruits. A series of novel quinolinyl thiourea analogues (11a-j) were synthesized by reaction of 3-aminoquinoline and corresponding isothiocyanates, i
- Mustafa, Muhammad Naeem,Saeed, Aamer,Channar, Pervaiz Ali,Larik, Fayaz Ali,Zain-ul abideen, Muhammad,Shabir, Ghulam,Abbas, Qamar,Hassan, Mubashir,Raza, Hussain,Seo, Sung-Yum
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- Hirshfeld surface analysis of some new heteroleptic Copper(I) complexes
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Seven new coordination complexes namely, [Cu(T1) (I) (PPh3)2] (CT1), [Cu(T2) (I) (PPh3)2] (CT2), [Cu(T3) (I) (PPh3)2] (CT3), [Cu(T4) (I) (PPh3)2] (CT4), [Cu(T5) (I) (P
- Mohd Zubir, Mohamad Zarif,Jamaludin, Nazzatush Shimar,Abdul Halim, Siti Nadiah
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p. 141 - 150
(2019/05/29)
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- Synthesis, crystal structure, spectral and electrochemical characterization, DNA binding and free radical scavenging studies of ferrocene-based thioureas
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Thioureas are important building blocks in medicinal chemistry; ferrocenes as highly hydrophobic moieties induce very interesting qualities in medicinal compounds. In this article, we have synthesized four ferrocene incorporated N,N′-disubstituted benzoyl
- Lal, Bhajan,Kanwal, Ammarah,Altaf, Ataf Ali,Badshah, Amin,Asghar, Faiza,Akhter, Sadia,Ullah, Shafiq,Khan, Syed Ishtiaq,Tahir, Muhammad Nawaz
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p. 2376 - 2392
(2019/08/26)
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- Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One-Pot Synthesis of Imines and Quinoxalines
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Three copper(I) complexes, [CuCl(L)(PPh3)2] [L = FL (1), BL (2) or TL (3)] were prepared from [(PPh3)2Cu(μ-Cl)2Cu(PPh3)] and N-carbamothioylfuran-2-carboxamide (FL), N-carbamothioylbenzamide (BL) or N-carbamothioylthiophene-2-carboxamide (TL) ligands in benzene and four-coordinated tetrahedral copper complexes were well characterized by various spectroscopic techniques (UV/Vis, FT-IR, 1H NMR, 13C NMR and 31P NMR). The molecular structure of the ligands (FL and BL) and complexes was established from single-crystal X-ray diffraction studies. Copper complexes have been shown to catalyse the one-pot synthesis of imines and quinoxalines. Heterogenized catalyst (4) was prepared by reacting more active complex 3 with polystyrene supported triphenylphosphane, and characterized by elemental analyses, and DRS-UV, FT-IR, ICP-OES, and solid-state NMR techniques. Catalytic activity of the complexes (3 and 4) was tested in the formation of imines from alcohols and amines, and quinoxalines from hydroxy ketones and diamines. Heterogeneity and reusability of catalyst 4 were evaluated, and the catalyst can be reused for four runs without any loss in activity.
- Sindhuja, Dharmalingam,Vasanthakumar, Punitharaj,Bhuvanesh, Nattamai,Karvembu, Ramasamy
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p. 3588 - 3596
(2019/08/20)
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- Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water
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In the present work, we have designed a novel, heterogeneous and recyclable magnetic Br?nsted acidic ionic liquid based on 5-phenyl-1H-tetrazole. The {Fe3O4@SiO2@CH2)35-phenyl-1H-tetrazole-SO3H/Cl} ([FSTet-SO3H]Cl) was prepared via the immobilization of 5-phenyl-1H-tetrazole-bonded sulfonic acid onto the surface of silica-coated magnetic nanoparticles using 3-chloropropyltriethoxysilane as a linker. The catalyst was characterized by XRD, TEM, FESEM, EDS, TG-DTA, and FT-IR. The ability and high activity of this catalyst were demonstrated in the synthesis of 1-carbamoyl-1-phenylureas with good to excellent yields via a new, simple and one-pot procedure in aqueous media under reflux conditions. This procedure has advantages such as high yields, short reaction times, a simple methodology and work-up process, green reaction conditions, high stability, catalytic activity, and easy preparation, separation and reusability of the catalyst. The synthesis of these compounds was confirmed by FT-IR, 1H NMR, 13C NMR and CHN. In addition, we investigated the biological properties of the 1-carbamoyl-1-phenylureas as newly synthesized compounds. The described catalyst could be easily separated from the reaction mixture by additional magnetic force and reused several times without a remarkable loss of its catalytic activity and any considerable changes in the product yield and the reaction time.
- Nasrollahzadeh, Mahmoud,Issaabadi, Zahra,Sajadi, S. Mohammad
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p. 27631 - 27644
(2018/08/16)
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- Mononuclear copper(I) complexes with triphenylphosphine and N,N′-disubstituted thioureas: synthesis, characterization, and biological evaluation
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Twelve new complexes, of the general formula CuCl(TPP)2Tu1–12 (Tu = thiourea), were synthesized by the reaction of CuCl(TPP)3 (TPP = triphenylphosphine) and various N,N′-disubstituted thioureas. The structures of the synthesized complexes were characterized by different techniques such as Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy (1H, 13C, 31P, and 19F), and the representative complexes (1, 2 and 12) were analyzed via single crystal X-ray diffraction. The single crystal X-ray analysis revealed that copper(I) is coordinated with chlorine, two TPP, and the thiourea ligands through the sulfur atom in a mononuclear distorted tetrahedral mode. The compounds were tested for antibacterial, antifungal, cytotoxicity, antileishmanial, and antioxidant activities. The results showed that the synthesized complexes are significantly more active than the free ligands and the commercial reference compounds. The high biological activities of the complexes versus free ligands can be attributed to the copper(I) chloride complexation with thiourea ligands. The synthesized complexes were also evaluated, both experimentally and theoretically, for DNA binding studies. The UV-visible spectroscopic and molecular docking studies demonstrated that the complexes are conjugating with DNA through a groove binding mode.
- Khan, Syed Ishtiaq,Ali Khan, Inayat,Badshah, Amin,Perveen Malik, Fouzia,Tabassum, Saira,Ullah, Ikram,Zargarian, Davit,Khawar Rauf, Muhammad
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p. 4086 - 4108
(2018/12/04)
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- Metal-mediated reactions towards the synthesis of a novel deaminolysed bisurea, dicarbamolyamine
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A new selective cobalt acetate tetrahydrate or cerium nitrate hexahydrate mediated cleavage of the C-N bond of a benzoyl isothiocyanate derivative to give (carbamoylamino)methanethioamide is presented. The cleavage of the C-N could not be achieved in the absence of thione. The novel silver-mediated conversion of a thione to the carbonyl was achieved on 1-((benzamido)formyl)urea and replicated on (carbamoylamino)methanethioamide to give the deaminolyzed bisurea (dicarbamolyamine). The compounds were characterized by IR, NMR, microanalysis and GC-MS. The single crystal X-ray diffraction studies of the crystal structures of compounds I, II, III and V is discussed.
- Odame, Felix,Hosten, Eric,Tshentu, Zenixole R.
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p. 535 - 543
(2018/06/21)
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- Kinetic-Mechanistic and Solid-State Study of the Oxidative Addition and Migratory Insertion of Iodomethane to [Rhodium(S,O-BdiPT or N,O-ox)(CO)(PR1R2R3)] Complexes
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Rhodium(I) carbonyl complexes containing bidentate X,O-Bid [S,O-BdiPT or N,O-ox; S,O-BdiPTH = N-benzoyl-N′,N′-(diphenyl)thiourea; N,O-oxH = 8-hydroxyquinoline] ligands of the form [Rh(X,O-Bid)(CO)(PR1R2R3)] (R1, R2, R3 = Ph or Cy) bearing different phosphine ligands, were investigated, the structural characterization of four example complexes is described and an extensive spectroscopic kinetic-mechanistic study of the oxidative addition of iodomethane thereto is discussed. Reaction with iodomethane led to RhIII-acyl species as secondary (final) products, whereas the primary RhIII-alkyl complexes, although rapidly formed, were only observed as intermediates, in small quantities for S,O-BdiPT (large S–Rh–O bite angle of 90–91°) but in significant amounts for N,O-ox complexes (less steric with a smaller N–Rh–O bite angle of 79–80°). Overall, almost an order-of-magnitude difference in rate constants was observed for the S,O-BdiPT complexes, with the PPh2Cy- and PPhCy2-bearing complexes showing the largest variation. In both the S,O-BdiPT and N,O-ox ligand systems an associative activation is inferred from the large negative ΔS≠ values. The relative reactivity of RhI-X,O-Bid complexes, where X = O, S or N, follows a surprising similar reactivity relationship when stepwise varying the PPh3, PPh2Cy, PPhCy2 and PCy3 tertiary phosphine ligands, suggesting a systematic behavior by the PR3 ligands, independent of the X,O-Bid ligand at the RhI metal center.
- Warsink, Stefan,Riekert Kotze,Janse van Rensburg, J. M. (Inus),Venter, Johan A.,Otto, Stefanus,Botha, Ebrahiem,Roodt, Andreas
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p. 3615 - 3625
(2018/09/11)
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- Phosphine-free direct conversion of carboxylic acids into acyl isothiocyanates using various electrophilic halogenation reagents
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In this study, the efficiency of some electrophilic halogen reagents including 2,4,6-trichloro-1,3,5-triazine, 2,4,4,6-tetrabromo-2,5-cyclohexadienone, 2-chloro-1-methylpyridinium iodide, N-bromosuccinimide, trichloroisocyanuric acid, and 1,3-dibromo-5,5-
- Khaje-Kolaki, Aslan,Mokhtari, Babak
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p. 805 - 808
(2018/09/26)
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- Optimization of 5-arylidene barbiturates as potent, selective, reversible LSD1 inhibitors for the treatment of acute promyelocytic leukemia
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Histone lysine specific demethylase 1 (LSD1) is overexpressed in diverse hematologic disorders and recognized as a promising target for blood medicines. In this study, molecular docking-based virtual screening united with bioevaluation was utilized to identify novel skeleton of 5-arylidene barbiturate as small-molecule inhibitors of LSD1. Among the synthesized derivatives, 12a exhibited reversible and potent inhibition (IC50 = 0.41 μM) and high selectivity over the MAO-A and MAO-B. Notably, 12a strongly induced differentiation effect on acute promyelocytic leukemia NB4 cell line and distinctly escalated the methylation level on histone 3 lysine 4 (H3K4). Our findings indicate that 5-arylidene barbiturate may represent a new skeleton of LSD1 inhibitors and 12a deserve as a promising agent for the further research.
- Xu, Siyuan,Zhou, Chen,Liu, Rongfeng,Zhu, Qihua,Xu, Yungen,Lan, Fei,Zha, Xiaoming
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p. 4871 - 4880
(2018/09/22)
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- Thiosemicarbazones and thiadiazines derived from fluorinated benzoylthioureas: Synthesis, crystal structure and anti-Trypanosoma cruzi activity
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A series of thiosemicarbazones was obtained by condensation of halogenated N-(diethylaminothiocarbonyl)benzimidoyl chlorides (3b–3h) with 4,4-dimethyl-3-thiosemicarbazide. The activity of the halogenated compounds against the parasite Trypanosoma cruzi was evaluated and compared to the previously reported activity of the corresponding non-substituted thiosemicarbazone. It was found that the halogen-substitution enhances in most cases the anti-parasitic activity. The meta-fluorinated compound (4g) was identified as the most potent one (IC50= 9.0 μM, CC50 > 200 μM), having a selectivity index (SI = IC50/CC50), which is 4-times higher than that of the non-substituted compound. Slight modification of the reaction conditions employed for the synthesis of some of the benzoylthioureas 3a–3g led to the unexpected formation of novel halogenated 6-amino-1,3,5-thiadiazine-2-thiones.
- Salsi, Federico,Bulh?es Portapilla, Gisele,Schutjajew, Konstantin,Carneiro, Zumira Aparecida,Hagenbach, Adelheid,de Albuquerque, Sérgio,da Silva Maia, Pedro Ivo,Abram, Ulrich
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- A cascade synthesis of: S -allyl benzoylcarbamothioates via Mumm-type rearrangement
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A catalyst and solvent free synthesis of S-allyl benzoylcarbamothioates has been achieved from the in situ generated benzoylcarbonimidothioates obtained by reacting MBH alcohols with aroyl isothiocyanates. An intramolecular thia-Michael addition of the in
- Dahiya, Anjali,Ali, Wajid,Alam, Tipu,Patel, Bhisma K.
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supporting information
p. 7787 - 7791
(2018/11/21)
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- Novel inhibitors of Staphylococcus aureus RnpA that synergize with mupirocin
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We recently discovered RnpA as a promising new drug discovery target for methicillin-resistant S. aureus (MRSA). RnpA is an essential protein that is thought to perform two required cellular processes. As part of the RNA degrasome Rnpa mediates RNA degradation. In combination with rnpB it forms RNase P haloenzymes which are required for tRNA maturation. A high throughput screen identified RNPA2000 as an inhibitor of both RnpA-associated activities that displayed antibacterial activity against clinically relevant strains of S. aureus, including MRSA. Structure-activity studies aimed at improving potency and replacing the potentially metabotoxic furan moiety led to the identification of a number of more potent analogs. Many of these new analogs possessed overt cellular toxicity that precluded their use as antibiotics but two derivatives, including compound 5o, displayed an impressive synergy with mupirocin, an antibiotic used for decolonizing MSRA whose effectiveness has recently been jeopardized by bacterial resistance. Based on our results, compounds like 5o may ultimately find use in resensitizing mupirocin-resistant bacteria to mupirocin.
- Lounsbury, Nicole,Eidem, Tess,Colquhoun, Jennifer,Mateo, George,Abou-Gharbia, Magid,Dunman, Paul M.,Childers, Wayne E.
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supporting information
p. 1127 - 1131
(2018/02/21)
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- Novel arylimino thiazole compound, preparation method and uses thereof
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The present invention relates to a compound with antibacterial synergy activity, a preparation and uses thereof, particularly to a novel arylimino thiazole compound, a preparation method and uses thereof, and specifically discloses a class of compounds represented by a formula (I) or optical isomers, cis-trans isomers or pharmaceutically acceptable salts thereof, a preparation method and uses thereof. The invention further discloses a pharmaceutical composition containing the compound. The compound of the present invention can effectively enhance the antibacterial activity of antibiotics, andcan be used for treating antibiotic-resistant bacteria. The formula (I) is defined in the specification.
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Paragraph 0125; 0126; 0127; 0128; 0162-0165; 0172-0175
(2018/03/28)
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- Design, synthesis and identification of novel substituted 2-amino thiazole analogues as potential anti-inflammatory agents targeting 5-lipoxygenase
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Human 5-Lipoxygenase (5-LOX) is a key enzyme targeted for asthma and inflammation. Zileuton, the only drug against 5-LOX, was withdrawn from the market due to several problems. In the present study, the performance of rationally designed conjugates of thi
- Sinha, Shweta,Doble, Mukesh,Manju
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- Chemoselective transfer hydrogenation of nitroarenes, ketones and aldehydes using acylthiourea based Ru(II)(p-cymene) complexes as precatalysts
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A new series of Ru(II)(η6-p-cymene) complexes (1–5) was synthesized from pyridine based acylthiourea ligands (L1-L5) and [Ru(η6-p-cymene)Cl2]2. All the ligands and complexes were well characterized by UV-Visible, FT-IR, mass and 1H & 13C NMR spectroscopic techniques. The molecular structures of the ligands (L1, L2, L4 and L5) and complex 1 were confirmed using single crystal X-ray diffraction study. The Ru(II)(η6-p-cymene) complexes (1–5) were proved to be efficient precatalysts for the transfer hydrogenation of carbonyl compounds and nitroarenes in the presence of 2-propanol as a hydrogen donor and KOH as a base. The catalytic transfer hydrogenation reactions were chemoselective towards the nitro group in presence of carbonyl group, which is a rare scenario in homogeneous catalysis. The catalyst was compatible with broad range of substrates which include furfural, quinone and many heterocycles. The catalytic reactions exhibited very high conversions (upto 100%) and excellent yields (upto 99%). Turn Over Number (TON) was found upto 990.
- Sathishkumar, Pushpanathan N.,Raveendran, Neethi,Bhuvanesh, Nattamai S.P.,Karvembu, Ramasamy
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- Bis-chelates of nickel(II) and copper(II) with an O,S-donor piperazine ligand
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Abstract: A bidentate O,S-donor ligand N-(4-benzoyl-piperazine-1-carbothioyl)-benzamide (HL) was synthesized from the reaction of in situ generated benzoylisothiocyanate with piperazine and benzoyl chloride. Reaction of HL with the perchlorate salts of Ni
- Mandal, Haridas
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p. 571 - 577
(2018/05/15)
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- Benzo[4,5]thiazolo[3,2-c][1,3,5,2]oxadiazaborinines: Synthesis, Structural, and Photophysical Properties
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A family of highly emissive benzo[4,5]thiazolo[3,2-c][1,3,5,2]oxadiazaborinines, conjugated with the donor 4-dimethylaminophenyl group, was designed and synthesized. Their photophysical, both in solution and in the solid state, and structural properties were investigated. The influence of donor and acceptor substituents (R) in the benzothiazole unit on photophysical properties of complexes was found out. The tetrafluorobenzothiazole analogue exhibits nonbonded nuclear spin-spin coupling between fluorines from the BF2 group and α-fluorine atom at the benzene ring. Additionally, this boron complex demonstrates a comparatively high solid-state fluorescence quantum yield (φ = 0.34).
- Potopnyk, Mykhaylo A.,Volyniuk, Dmytro,Ceborska, Magdalena,Cmoch, Piotr,Hladka, Iryna,Danyliv, Yan,Gra?ulevi?ius, Juozas Vidas
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p. 12129 - 12142
(2018/09/25)
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- Synthesis, characterization, and in?vitro evaluation and in silico molecular docking of thiourea derivatives incorporating 4-(trifluoromethyl)phenyl moiety
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A series of acyl thiourea derivatives bearing 4-(trifluoromethyl)phenyl moiety (7 compounds) has been synthesized and characterized by FT-IR, 1H and 13C NMR spectroscopy and elemental analyses. The molecular structure of five compounds (2, 4, 5, 6 and 7) was determined by single crystal X-ray diffraction analysis. The crystal structures revealed that the carbonyl thiourea units in all determined compounds are mostly planar due in part to the formation of intramolecular N[sbnd]H?O[dbnd]C and C[sbnd]H?S[dbnd]C hydrogen bonds that form two S (6) rings. The intermolecular contacts of five crystal structures have been preformed based on the Hirshfeld surface and their associated 2D fingerprint plots. All the synthesized compounds were preliminarily screened for their in?vitro anti-fungal activity. Especially, compounds 4, 5 and 6 showed a good anti-fungal activity for four different kinds of fungi. Furthermore, all prepared thiourea derivatives were screened for antioxidant potential activity by DPPH free radical scavenging and the excellent activity were found compounds 5 and 6 with the IC50value of 191.75?μg/mL and 189.75?μg/mL, respectively. In silico molecular docking studies were performed to screen the thiourea derivatives against heat shock protein HSP90.
- Qiao, Lei,Huang, Jie,Hu, Wei,Zhang, Yu,Guo, Jiajia,Cao, Wenli,Miao, Kanghua,Qin, Baofu,Song, Jirong
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p. 149 - 159
(2017/03/22)
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