- Cu(II) and Zn(II) complexes from a thiosemicarbazone derivative: Investigating the intermolecular interactions, crystal structures and cytotoxicity
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Two complexes of Cu(II) and Zn(II) were prepared from a thiosemicarbazone derivative (H2esct) using their corresponding metal acetates and 2,2′-bipyridine as base. The complexes were characterized by elemental analyses, UV–visible, FT-IR and NM
- Mathews, Nimya Ann,Jacob, Jinsa Mary,Sabura Begum,Kurup, M.R. Prathapachandra
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- Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5-dichlorosalicylaldehyde-N4-cyclohexylthiosemicarbazone
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A 3,5-dichlorosalicylaldehyde-N4-cyclohexylthiosemicarbazone (C14H16Cl2N3OS) and its complexes [Zn(dsct)(phen)]·DMF (1), [Zn(dsct)(bipy)]·DMF (2), [Cu(dsct)(bipy)]·DMF (3) (phen?=?1,10-phenathroline,
- Mathews, Nimya Ann,Begum, P.M. Sabura,Kurup, M.R. Prathapachandra
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- Synthesis of oxadiazole-thiadiazole hybrids and their anticandidal activity
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In the field of infection management, it is a major challenge to discover a potent and safe antifungal agent due to the emergence of resistant strains. Hence, the goal of this paper is to design and synthesize novel oxadiazole-thiadiazole hybrid compounds
- Levent, Serkan,?avu?o?lu, Betül Kaya,Sa?l?k, Begüm Nurpelin,Osmaniye, Derya,?evik, Ulviye Acar,Atl?, ?zlem,?zkay, Yusuf,Kaplanc?kl?, Zafer As?m
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- Synthesis, characterization, and antibacterial activities of organotin(IV) complexes with 2-acetylpyridine-N(4)-cyclohexylthiosemicarbazone (HAPCT)
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The reaction of 2-acetylpyridine-N(4)-cyclohexylthiosemicarbazone [(HAPCT), (1)] ligand with organotin(IV) chloride(s) afforded the five new organotin(IV) complexes: [MeSnCl2(APCT)] (2), [BuSnCl2(APCT)] (3), [PhSnCl2(APCT)] (4), [Me2SnCl(APCT)] (5), and [Ph 2SnCl(APCT)] (6). The ligand (1) and its organotin(IV) complexes (2-6) have been synthesized and characterized by CHN analyses, molar conductivity, UV-vis, FT IR, 1H, 13C, and 119Sn NMR spectral studies. The single crystal X-ray diffraction studies indicated that [PhSnCl2(APCT)] (4) is six coordinated and strongly adopts a distorted octahedral configuration with the coordination through pyridine-N, azomethine-N, and thiolato-S atoms of the ligand. The compound crystallizes into a monoclinic lattice with the space group P21/n. The ligand (1) and its organotin(IV) complexes (2-6) were assayed for in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli, Enterobacter aerogenes, and Salmonella typhi. The screening results have shown that the organotin(IV) complexes (2-6) have better antibacterial activity than the free ligand. Furthermore, it has been shown that the diphenyltin(IV) derivative (6) exhibits significantly better activities than the other organotin(IV) derivatives (2-5).
- Salam,Affan,Arafat, Md. Azharul,Saha, Ramkrishna,Nasrin, Runia
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- Synthesis, crystal structures, and biological evaluation of manganese(II) and nickel(II) complexes of 4-cyclohexyl-1-(1-(pyrazin-2-yl)ethylidene) thiosemicarbazide
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4-Cyclohexyl-1-(1-(pyrazin-2-yl)ethylidene)thiosemicarbazide (HL) and its transition metal complexes formulated as [Mn(L)2] (1) and [Ni(L) 2] (2) have been prepared in 55-75% yield and characterized by elemental analysis, IR, MS, NMR
- Li, Ming Xue,Zhang, Li Zhi,Zhang, Dong,Ji, Bian Sheng,Zhao, Jun Wei
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- Organotin(IV) complexes of 2-hydroxyacetophenone-N(4)- cyclohexylthiosemicarbazone (H2dact): Synthesis, spectral characterization, crystal structure and biological studies
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Four new organotin(IV) complexes of the type [MeSnCl(dact)] (2), [BuSnCl(dact)] (3), [PhSnCl(dact)] (4) and [Ph2Sn(dact)] (5) were synthesized by the direct reaction of 2-hydroxyacetophenone-N(4)- cyclohexylthiosemicarbazone [H2dact,
- Affan,Salam,Ahmad, Fasihuddin B.,White, Fraser,Ali, Hapipah M.
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- Synthesis and crystal structure of new monometallic and bimetallic copper(II) complexes with N-substituted isatin thiosemicarbazone ligands: Effects of the complexes on DNA/protein-binding property, DNA cleavage study and in vitro anticancer activity
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A novel series of N-substituted isatin thiosemicarbazone ligands (L1–L3) and their copper(II) complexes [Cu(II)(ITSC)] were synthesized and characterized by elemental analyses and UV–Vis, FT-IR,1H &13C NMR/EPR and mass spectroscopic
- Muralisankar, Mathiyan,Sujith, Surendran,Bhuvanesh, Nattamai S.P.,Sreekanth, Anandaram
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- Unusual isolation of a hemiaminal product from 4-cyclohexyl-3- thiosemicarbazide and di-2-pyridyl ketone: Structural and spectral investigations
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Stable hemiaminal product was isolated as single crystals from the condensation reaction of di-2-pyridyl ketone with 4-cyclohexyl-3- thiosemicarbazide and structurally and spectrochemically characterized. The compound is the first report of a stable hemia
- Suni,Kurup, M.R. Prathapachandra,Nethaji, Munirathinam
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- Synthesis and spectroscopic characterization of organotin(IV) complexes with 2-benzoylpyridine-N(4)-cyclohexylthiosemicarbazone (HBPCT): X-ray crystal structure of [PhSnCl2(BPCT)]
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The reaction of 2-benzoylpyridine-N(4)-cyclohexylthiosemicarbazone [HBPCT, (1)] ligand with organotin(IV) chloride(s) lead to the formation of three new organotin(IV) complexes: [MeSnCl2(BPCT)] (2), [PhSnCl 2(BPCT)] (3) and [Ph2
- Affan,Salam,Ahmad, Fasihuddin B.,Ismail,Shamsuddin, Mustaffa B.,Ali, Hapipah M.
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- Synthesis, characterization, antibacterial, and cytotoxic activities of organotin(IV) complexes derived from N (4)-cyclohexylthiosemicarbazone: X-ray crystal structure of [Ph2SnCl(L)]
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Reaction of organotin(IV) chloride(s) with 2-benzoylpyridine-N(4)- cyclohexylthiosemicarbazone, [HL] (1) yielded [MeSnCl2(L)] (2), [BuSnCl2(L)] (3), [Me2SnCl(L)] (4), and [Ph 2SnCl(L)] (5). The ligand (1) and it
- Salam,Affan,Ahmad, Fasihuddin B.,Arafath, Md. Azharul,Tahir, M. Ibrahim Mohamed,Shamsuddin, Mustaffa B.
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- Synthesis, crystal structures and biological activities of 2-acetylpyridine N(4)-cyclohexylthiosemicarbazone and its manganese(II) and nickel(II) complexes
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2-Acetylpyridine N(4)-cyclohexylthiosemicarbazone (HL) and its manganese(II) and nickel(II) complexes formulated as [Mn(L)2] (1) and [Ni(L)2] (2) have been synthesized and characterized by elemental analysis, infrared spectra, mass s
- Li, Ming-Xue,Zhang, Dong,Zhang, Li-Zhi,Niu, Jing-Yang,Ji, Bian-Sheng
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- Synthesis, spectral characterization and crystal structure of 2-benzoylpyridine N(4)-cyclohexylthiosemicarbazone
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The synthesis, characterization, molecular and crystal structure of 2-benzoylpyridine N(4)-cyclohexylthiosemicarbazone is reported. IR analysis was done and NMR assignments using COSY homonuclear and HMQC heteronuclear correlation techniques were carried
- Joseph, Marthakutty,Suni,Nayar, Chandini R.,Kurup, Maliyeckal R. Prathapachandra,Fun, Hoong-Kun
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- Synthesis and characterization of tin(IV)/organotin(IV) complexes with 2-benzoylpyridine-N(4)-cyclohexylthiosemicarbazone [HBPCT]: X-ray crystal structure of [SnCl3(BPCT)]
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Four new tin(IV)/organotin(IV) complexes, [SnCl3(BPCT)] (2), [MeSnCl2(BPCT)] (3), [Me2SnCl(BPCT)] (4), and [Ph2SnCl(BPCT)] (5), have been synthesized by the direct reaction of 2-benzoylpyridine-N(4)- cyclohexylthiosemicarbazone [HBPCT, (1)] and
- Salam,Affan,Ahmad, Fasihuddin B.,Hitam, Ramli B.,Gal, Zoltan,Oliver, Presly
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- Bismuth(III) complexes with pyrazineformamide thiosemicarbazones: Investigation on the antimicrobial and cytotoxic effects
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Complexes [Bi(PzAm4DH)Cl2] (1), [Bi(PzAm4M)Cl2] (2), [Bi(PzAm4E)Cl2] (3), [Bi(PzAm4Cy)Cl2]?3H2O (4) and [Bi(PzAm4Ph)Cl2] (5) were prepared with 2-pyrazineformamide- (HPzAm4DH, L1), N(4)-met
- Almeida, Jéssica C. L.,Amim, Raquel S.,Lessa, Josane A.,Louren?o, Maria C. S.,Mendes, Isolda C.,Pessoa, Claudia
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- Synthesis, structural, and spectral studies of diorganotin(IV) complexes with 2-hydroxy-5-methylbenzaldehyde-N (4)-cyclohexylthiosemicarbazone
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Three new diorganotin(IV) complexes, [Me2Sn(L)] (2), [Bu2Sn(L)] (3), and [Ph2Sn(L)] (4) [where H2L (1) = 2-hydroxy-5-methylbenzaldehyde-N(4)-cyclohexylthiosemicarbazone] have been synthesized by reacting the cor
- Haque, Rosenani A.,Salam
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- Novel heterocyclic thiosemicarbazones derivatives as colorimetric and "turn on" fluorescent sensors for fluoride anion sensing employing hydrogen bonding
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(Chemical Equation Presented) Two novel heterocyclic thiosemicarbazone derivatives have been synthesized, and characterized, by means of spectroscopic and single crystal X-ray diffraction methods. Their chromophoric-fluorogenic response towards anions in
- Kumar, S. L. Ashok,Kumar, M. Saravana,Sreeja,Sreekanth
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- Experimental and theoretical studies of novel hydroxynaphthalene based chemosensor, and construction of molecular logic gates
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2-Hydroxynaphthalenyl-N(4)-cyclohexyl thiosemicarbazone (CHNT) was synthesized and characterized for selective sensing of fluoride, cyanide and copper ions. The interaction between CHNT with fluoride, cyanide and copper ions have been investigated through
- Basheer, Sabeel M.,Bhuvanesh, Nattamai S.P.,Sreekanth, Anandaram
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- Pyridoxal hydrochloride thiosemicarbazones with copper ions inhibit cell division via Topo-I and Topo-IIɑ
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Topoisomerase (Topo) accelerates cell growth and division, and has been a theoretical target for anti-cancer drugs for decades. A series of pyridoxal thiosemicarbazone (PLT) ligands were designed and synthesized, and the dependence of their antiproliferative activity on copper was investigated. The insertion of N-cyclohexyl-2-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)-N-methylhydrazinecarbothioamide hydrochloride (compound 9) and Chlorido(N-cyclohexyl-2-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)-N-methylhydrazinecarbothioamide hydrochloride-O,N,S)?copper(II) nitrate (9-Cu complex) into Topo-I and Topo-II prevented uncoiling of DNA through hydrogen bonds and intermolecular forces. The combination of PLT derivatives and copper gluconate (CuGlu) improved their anti-tumour activity against a cell line with high expression of topoisomerase (SK-BR-3). The non-linear regression equations of the inhibitory activity and anti-tumour activity of Topo-I and Topo-IIɑ in SK-BR-3 cells had R2 values of 0.93 and 0.94, respectively. In addition to lipophilicity, inhibition of topoisomerase also affected the activity of PLT ligands by coordinating with copper ions. At the cellular level, PLTs and CuGlu penetrate the cell membrane to form metabolites in the cell, thus selectively inhibiting the activity of Topo-I and Topo-IIɑ, and ultimately inhibiting cell division. These findings will inform the design of future anti-cancer thiosemicarbazone drugs.
- Ai, Yu,Chen, Mengyao,Li, Bin,Qi, Jinxu,Zheng, Xinhua,Zheng, Yunyun
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- CERTAIN NEW 4-(2-((5-(SUBSTITUTEDAMINO)-1,3,4-THIADIAZOLE-2-YL)THIO)ACETYL)BENZENESULPHONEAMIDE DERIVATIVES AND A METHOD FOR THE SYNTHESIS OF SAID DERIVATIVES
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The invention relates to a certain new 4-(2-((5-(substitutedamino)-1,3,4-thiadiazole-2-yl)thio)acetyl)benzenesulphonamide derivatives for use in pharmaceutics, chemical and pharmaceutical industry, and to a method for the synthesis of said derivatives.
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(2022/04/02)
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- Diaryl-substituted thiosemicarbazone: A potent scaffold for the development of New Delhi metallo-β-lactamase-1 inhibitors
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The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has become an emerging public health threat. Inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. A potent scaffold, diaryl-substituted thiosemicarbazone, was constructed and assayed with metallo-β-lactamases (MβLs). The obtained twenty-six molecules specifically inhibited NDM-1 with IC50 0.038–34.7 μM range (except 1e, 2e, and 3d), and 1c is the most potent inhibitor (IC50 = 0.038 μM). The structure-activity relationship of synthetic thiosemicarbazones revealed that the diaryl-substitutes, specifically 2-pyridine and 2-hydroxylbenzene improved inhibitory activities of the inhibitors. The thiosemicarbazones exhibited synergistic antimycobacterial actions against E. coli-NDM-1, resulted a 2–512-fold reduction in MIC of meropenem, while 1c restored 16–256-, 16-, and 2-fold activity of the antibiotic on clinical isolates ECs, K. pneumonia and P. aeruginosa harboring NDM-1, respectively. Also, mice experiments showed that 1c had a synergistic antibacterial ability with meropenem, reduced the bacterial load clinical isolate EC08 in the spleen and liver. This work provided a highly promising scaffold for the development of NDM-1 inhibitors.
- Li, Jia-Qi,Sun, Le-Yun,Jiang, Zhihui,Chen, Cheng,Gao, Han,Chigan, Jia-Zhu,Ding, Huan-Huan,Yang, Ke-Wu
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- Synthesis and Antiproliferative Activity of New Thiosemicarboxamide Derivatives
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To discover new anticancer agents, two series of thiosemicarboxamide derivatives were synthesized and evaluated for their antiproliferative activity against human cancer cells in vitro. Most target compounds (especially 3f, 3g, and 3h) exhibit potent antiproliferative activity against HeLa cells. Importantly, compound 3h, bearing a 4-methylphenyl substituent at N position of thiourea moiety, has significant and broad-spectrum inhibitory activities against cancer cells (HepG2, HeLa, MDA-MB231, A875, and H460 cells) with low IC50 values (5.0 μM) and shows low toxicity to normal LO2 and MRC-5 cells. Further studies show that compound 3h exerts high inhibitory activity in cancer cells by inducing the G2/M-phase arrest of cancer cells. Collectively, this study presents compound 3h as a new entity for the development of cell cycle arrest inducers for the treatment of cancer.
- Chen, Jun,Fang, Meijuan,Guo, Yafei,Hu, Hongyu,Hu, Sangsang,Sun, Ke,Wu, Jun,Xue, Yuhua
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- Novel thiosemicarbazone derivatives: In vitro and in silico evaluation as potential mao-b inhibitors
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MAO-B inhibitors are frequently used in the treatment of neurodegenerative diseases such as Parkinson’s and Alzheimer’s. Due to the limited number of compounds available in this field, there is a need to develop new compounds. In the recent works, it was shown that various thiosemicarbazone derivatives show hMAO inhibitory activity in the range of micromolar concen-tration. It is thought that benzofuran and benzothiophene structures may mimic structures such as indane and indanone, which are frequently found in the structures of such inhibitors. Based on this view, new benzofuran/benzothiophene and thiosemicarbazone hybrid compounds were synthesized, characterized and screened for their hMAO-A and hMAO-B inhibitory activity by an in vitro fluorometric method. The compounds including methoxyethyl substituent (2b and 2h) were found to be the most effective agents in the series against MAO-B enzyme with the IC50 value of 0.042 ± 0.002 μM and 0.056 ± 0.002 μM, respectively. The mechanism of hMAO-B inhibition of compounds 2b and 2h was investigated by Lineweaver–Burk graphics. Compounds 2b and 2h were reversible and non-competitive inhibitors with similar inhibition features as the substrates. The Ki values of compounds 2b and 2h were calculated as 0.035 μM and 0.046 μM, respectively, with the help of secondary plots. The docking study of compound 2b and 2h revealed that there is a strong interaction between the active sites of hMAO-B and analyzed compound.
- ?zkay, Yusuf,Kaplanc?kl?, Zafer As?m,Kurban, Berkant,Levent, Serkan,Osmaniye, Derya,Sa?l?k, Begüm Nurpelin
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- Insight on a new indolinone derivative as an orally bioavailable lead compound against renal cell carcinoma
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A series of novel 3-indolinone-thiazolidinones and oxazolidinones 4a-k was synthesized via molecular hybridization approach and sequentially evaluated to explore its cytotoxic activity. The cytotoxicity screening pointed toward the N-cyclohexyl thiazolidinone derivative 4f that revealed promising renal cytotoxicity against CAKI-1 and UO-31 renal cancer cell lines with IC50 values 4.74 and 3.99 μM, respectively, which were comparable to those of sunitinib along with good safety threshold against normal renal cells. Further emphasis on compound 4f renal cytotoxicity was achieved via different enzyme assays and CAKI-1 and UO-31 cell cycle analysis. The results were supported by in silico studies to explore its physicochemical, pharmacokinetic and drug-likeness properties. Finally, compound 4f was subjected to an in vivo pharmacokinetic study through two different routes of administration showing excellent oral bioavailability. This research represents compound 4f as a promising candidate against renal cell carcinoma.
- Fouad, Marwa A.,Zaki, Mayssoune Y.,Lotfy, Raghda A.,Mahmoud, Walaa R.
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- One pot synthesis of schiff base complexes of Cu(II), Zn(II), Ni(II), Co(II) and their cytotoxicity, molecular docking and antibacterial activity
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A novel Schiff base ligand (L), N(4)-cyclohexyl-2-(1-(5-chlorothiophen-2-yl)ethylidene)hydrazine carbothioamide was synthesized from isothiocyanatocyclohexane and hydrazine. All the synthesized transition metal(II) complexes were characterized by function
- ASHMA,SUDHA,ASHOK KUMAR,SASIKUMAR,ASKAR ALI
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p. 2507 - 2514
(2020/10/22)
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- Synthesis of novel quinoline-thiosemicarbazide hybrids and evaluation of their biological activities, molecular docking, molecular dynamics, pharmacophore model studies, and ADME-Tox properties
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In the present study, a novel series of N-((substituted)carbamothioyl)-2,4-dimethylquinoline-3-carboxamide (7a-7s) was synthesized by microwave-assisted method. Structure of these derivatives was examined by spectroscopic techniques such as 1H NMR, 13C NMR, FT-IR, and ESI-MS. Further, the novel synthesized compounds were evaluated for their in-vitro biological activities against antibacterial, antifungal, antimalarial, and antituberculosis activity as well as for in-silico study. The antimalarial results demonstrated that compounds 7c and 7q (0.02 μg/mL) have notable potency against Plasmodium falciparum compared with chloroquine (0.02 μg/mL); compounds 7l (0.10 μg/mL), 7e, 7s (0.19 μg/mL), 7b, 7p (0.15 μg/mL), 7a, 7f, and 7f (0.25 μg/mL) also exhibited good activity against P. falciparum compared with quinine (0.26 μg/mL) as standard drug. Docking was performed on PFDHFR-TS, given the effect of compounds against the P. falciparum strain was excellent in comparison with standard drug. Molecular docking suggested that compounds 7b, 7i and 7c, 7e, and 7l closely bind with the active site of protein 3JSU and 4DP3, respectively, and compared with biological activity. We have also carried out molecular dynamics simulation on the best dock compound 7e complex with PDB: 3JSU to check the stability of docked complex and their molecular interaction. The calculated ADME-Tox descriptors for the synthesized compounds validated good pharmacokinetics properties, suggesting that these compounds could be used as hit for the development of the new active agents.
- Darji, Drashti G.,Patel, Dhaval B.,Patel, Hitesh D.,Patel, Krupa R.,Rajani, Dhanji P.,Rajani, Smita D.
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- Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives
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Schiff-base–bearing new bis(thiosemicarbazone) derivatives were prepared from terephthalaldehyde and various thiosemicarbazides. FT–IR, 1 H NMR, 13 C NMR, and UV–Vis spectroscopic methods and elemental analysis were used to elucidate
- Yakan, Hasan
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p. 1085 - 1099
(2020/09/16)
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- A thiosemicarbazone derivative induces triple negative breast cancer cell apoptosis: possible role of miRNA-125a-5p and miRNA-181a-5p
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Background: Breast cancer, the most commonly diagnosed malignancy in women, accounts for the highest cancer-related deaths worldwide. Triple negative breast cancer (TNBC), lacking the expression of estrogen, progesterone and HER2 receptors, has an aggressive clinical phenotype and is susceptible to chemotherapy but not to hormonal or targeted immunotherapy. In an attempt to identify potent and selective anti-TNBC agents, a set of thiosemicarbazone derivatives were screened for their cytotoxic activity against MDA-MB 231 breast cancer cell line. Methods: MTT assay was used to examine cell viability. P53 phosphorylation status, poly (ADP-ribose) polymerase (PARP) cleavage as well as Bcl2 and Bax protein levels were assessed by Western blot. Quantitative Real Time-PCR was carried out to characterize miRNAs expression levels. Results: Combining Cisplatin + thiosemicarbazone compound 4 showed potent anti-TNBC potential. Cisplatin + compound 4 significantly enhanced p53 phosphorylation, induced Bax amount, reduced Bcl2 protein levels, enhanced PARP cleavage and modulated miRNAs expression profile in TNBCs, with a particular overexpression of miR-125a-5p and miR-181a-5p. Intriguingly, miR-125a-5p and miR-181a-5p could significantly downregulate BCL2 expression by binding to their target sites in the 3′UTR. Conclusions: Collectively, our results demonstrate an anti-TNBC activity of Cisplatin + thiosemicarbazone compound 4 combination mediated via induction of apoptosis.
- El Majzoub, Rania,Fayyad-kazan, Mohammad,Nasr El Dine, Assaad,Makki, Rawan,Hamade, Eva,Grée, René,Hachem, Ali,Talhouk, Rabih,Fayyad-Kazan, Hussein,Badran, Bassam
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p. 1431 - 1443
(2019/11/03)
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- Synthesis and biological evaluation of new thiosemicarbazone derivative schiff bases as monoamine oxidase inhibitory agents
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Twenty-six novel thiosemicarbazone derivative B1–B26 were synthesized via condensation reactions between the corresponding thiosemicarbazides and aldehydes. The chemical characterization of the compounds was carried out by infrared (IR), mass (MS), proton and carbon nuclear magnetic resonance (1H- and 13C-NMR) spectroscopic analyses. The compounds were investigated for their monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) inhibitory activity and most of them were more potent against MAO-A enzyme when compared with MAO-B enzyme. N-Cyclohexyl-2-[4-[(4-chlorophenyl)thio]benzylidene]hydrazine-1-carbothioamide (B24) was the most active compound against MAO-A. The enzyme kinetics study revealed that compound B24 has a reversible and competitive mode of binding. Interaction modes between compound B24 and MAO-A were clarified by docking studies. In addition, the favourable absorption, distribution, metabolism, and excretion (ADME) properties and non-toxic nature of compound B24 make this compound a promising MAO-A inhibitor.
- ?avu?o?lu, Betül Kaya,Sa?l?k, Beg m Nurpelin,Sa?l?k, Begüm Nurpelin,Osmaniye, Derya,Levent, Serkan,Evik, Ulviye Acar,Karaduman, Abdullah Burak,Zkay, Yusuf,Kaplanc?kl?, Zafer As?m
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- Synthesis, characterization and biological evaluation of novel 1-N-substituted thiocarbomoyl-3-ferrocenyl-2-pyrazoline derivatives
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Some novel 1-N-substituted thiocarbomoyl-3-ferrocenyl-2-pyrazoline derivatives were synthesized and evaluated for in vitro antiamoebic activity against HM1:IMSS strain of Entamoeba histolytica. The results showed that most of the compounds exhibited promising activity (IC50 values in the range of 0.050-1.683 μM) than the reference drug metronidazole (IC50 = 1.78 μM). Active compounds were further screened for cytotoxicity against human embryonic kidney-293 (HEK-293) normal cell lines to ensure their toxic effect and the results revealed that active compounds were least toxic in the concentration range of 2.5-50 μM for 48 h and 2.5-25 μM for 72 h. At 100 μM for 48 h and at 50 μM for 72 h only four compounds 2c, 2h, 2k and 2l showed maximum viability and least cytotoxicity, respectively, concluding that all the screened compounds were least cytotoxic against human embryonic kidney-293 (HEK-293) normal cell lines in the concentration range of 2.5-50 and 2.5-25 μM.
- Parveen, Humaira,Alatawi, Raedah Aiyed Suliman,Khan, Salman Ahmad,Al-Ahmdi, Mohammed Issa,Mukhtar, Sayeed,Azam, Amir,Elsayed, Nadia H.
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p. 1835 - 1840
(2016/07/06)
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- Synthesis and antimicrobial activity of tetradentate ligands bearing hydrazone and/or thiosemicarbazone motifs and their diorganotin(IV) complexes
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Four novel ligands derived from 2,3-butanedione have been synthesized, two dissymmetric thiosemicarbazone/3-hydroxy-2-naphthohydrazone ligands, H2L1 (bearing 4-isopropyl-3-thiosemicarbazone) and H2L2 (containing
- González-García, Cristina,Mata, Alejandro,Zani, Franca,Mendiola, M. Antonia,López-Torres, Elena
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p. 118 - 130
(2016/11/09)
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- Spectroscopic and TD-DFT studies on the turn-off fluorescent chemosensor based on anthraldehyde N(4) cyclohexyl thiosemicarbazone for the selective recognition of fluoride and copper ions
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The copper and fluoride ions sensing mechanism of a chemosensor based on anthraldehyde N(4) cyclohexyl thiosemicarbazone (AntCy) was investigated via colorimetric, fluorescence, electrochemical and NMR titration studies. Detailed investigations on their s
- Basheer, Sabeel M.,Willis, Anthony C.,Pace, Ron J.,Sreekanth, Anandaram
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- An efficient synthesis of novel carbohydrate and thiosemicarbazone hybrid benzimidazole derivatives and their antimicrobial evaluation
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A library of thiosemicarbazide hybrid 2-(aldo-polyhydroxyalkyl)benzimidazole derivatives have been designed and synthesized with simple and eco-friendly methodologies. The structures of the compounds have been elucidated with the aid of elemental analysis, IR, mass and 1H NMR spectral data. These novel synthesized compounds have been evaluated for their antibacterial activity against two gram-positive bacteria (S. aureus and S. pyogenus) and two gram-negative bacteria (P. aeruginosa and E. coli). The title compounds have also been studied for their antifungal activity against C. albicans, A. niger and A. clavatus using the broth dilution technique.
- Panchal, Shyamali N.,Vekariya, Rajesh H.,Patel, Kinjal D.,Prajapati, Shraddha M.,Rajani, Dhanji P.,Rajani, Smita D.,Patel, Hitesh D.
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p. 604 - 612
(2017/01/18)
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- Synthesis of some novel thiosemicarbazone derivatives having anti-cancer, anti-HIV as well as anti-bacterial activity
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Some new thiosemicarbazones containing benzimidazole moiety have been synthesized and their ability to inhibit growth of 60 human cancer cell lines, in vitro replication of HIV virus strains as well as inhibition capacity for various bacterial strains have been evaluated. One compound 2-|l-(5-chloro-l//- benzimidazol-2-yl) ethylidene] N-phenylhydrazincarbothioamide (S2) (NSC 92491) has been selected for five dosage screening and shows remarkable anticancer activity along with good anti-HIV and anti-bacterial activities. The structures of all the compounds have been confirmed by FT-IR, NMR, and Mass spectra and by elemental analysis.
- Patel, Hitesh Dahyabhai,Divatia, Saavani Malove,De Clercq, Erik
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p. 535 - 545
(2013/06/26)
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- Augmentation of GABAergic neurotransmission by novel N-(substituted)-2-[4- (substituted)benzylidene]hydrazinecarbothioamides - A potential anticonvulsant approach
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New N-(substituted)-2-[4-(substituted)benzylidene]hydrazinecarbothioamides were designed, synthesized and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity was established in three seizure models i.e. MES, scMET and 6 Hz model. The most active compound was N-(4-methoxyphenyl)-2-[4-(4-methylphenoxy) benzylidene]hydrazinecarbothioamide PT 30 which showed 100% protection in both MES and 6 Hz test. Compound PT 30 showed protection at three different time points in 6 Hz test at a dose of 100 mg/kg. Compound 2-[4-(4-Chlorophenoxy)benzylidene]-N-cyclohexylhydrazine carbothioamide PT 4 was also found to be active in both MES and 6 Hz test. Titled compounds exhibited good binding properties with epilepsy molecular targets GABA (A) delta and GABA (A) alpha-1 receptors, in LGA based flexible docking studies. Compounds PT 30 and PT 4 were found to elevate γ-aminobutyric acid (GABA) levels in the midbrain and medulla oblongata regions of rat brain. A computational study was carried out for calculation of pharmacophore pattern and prediction of pharmacokinetic properties.
- Tripathi, Laxmi,Kumar, Praveen
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p. 477 - 487
(2013/07/19)
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- Synthesis, spectral characterization and crystal structure of a novel trinuclear di-n-butyltin(IV) complex with pyruvic acid-N(4)- cyclohexylthiosemicarbazone (H2PACT)
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A new trinuclear di-n-butyltin(IV) complex with pyruvic acid-N(4)-cyclohexylthiosemicarbazone (H2PACT) ligand was synthesized and characterized by elemental analyses, molar conductivity, UV-Vis, FT-IR, 1H, 119Sn NMR spectroscopy and single crystal X-ray study. Single crystal X-ray diffraction data revealed that this complex was trinuclear cyclic fashion with the pyruvic acid-N(4)-cyclohexylthiosemicarbazone ligand. In the trinuclear di-n-butyltin(IV) complex, the ligand (H2PACT) is coordinated to the central tin(IV) atoms via the carboxylato-O, the azomethine-N and the thiolato-S atoms. The trinuclear tin system is formed by the bridges through the carbonyl oxygen atom of the carboxylate moieties and making the tin atom of seven coordinated in distorted pentagonal bipyramidal geometry. Single crystal X-ray data indicates that the complex (1) crystallized in cubic system with space group I-43d, a = b = c = 30.3273(17) , α = β = γ = 90°, Z = 16, μ(MoKα) = 1.209 mm-1, F(000) = 12,144, and final R1 = 0.0390, wR2 = 0.0843 for observed reflections 4582(I > 2σ(I)).
- Salam,Affan,Ahmad, Fasihuddin B.,Jusoh,Shamsuddin, Mustaffa B.,Yamin, Bohari,Farina, Yang
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experimental part
p. 4202 - 4206
(2012/01/13)
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- Triorganotin(IV) complexes of pyruvic acid-N(4)-cyclohexylthiosemicarbazone (HPACT): Synthesis, characterization, crystal structure and in vitro antibacterial activity
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The reaction of triorganotin(IV) chloride with pyruvic acid-N(4)- cyclohexylthiosemicarbazone (HPACT) afforded the complexes [Bu 3Sn(PACT)] (1) and [Ph3Sn(PACT)] (2). The ligand HPACT and its two triorganotin(IV) complexes 1 and 2 ha
- Affan,Salam,Ahmad, Fasihuddin B.,Hitam, Ramli B.,White, Fraser
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experimental part
p. 19 - 24
(2012/03/09)
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- New palladium and platinum complexes with bioactive 3,5-diacetyl-1,2,4- triazol bis(4-cyclohexyl thiosemicarbazone) ligand: Chemistry, antiproliferative activity and preliminary toxicity studies
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The preparation and characterization of the new 3,5-diacetyl-1,2,4-triazol bis(4-cyclohexyl thiosemicarbazone) ligand, H5L1, is described. Treatment of H5L1 with K2PtCl 4 gave the dinuclear complex [Pt(H3L1)] 2, 1, but using MCl2(PPh3)2 where M = Pd or Pt, mononuclear complexes 2 and 3, of general formula [M(H 3L1)PPh3], were obtained. Subsequent reaction of the [Pd(H3L1)PPh3] complex with PdCl 2(PPh3)2 yielded a new dinuclear complex [(PPh3)Pd(H2L1)PdCl], 4. All compounds have been characterized by elemental analysis and FAB+ spectrometry and by IR and NMR spectroscopy. The molecular structures of mononuclear complexes 2 and 3 and dinuclear complex 4 have been determined by X-ray crystallography. The new compounds synthesized have been evaluated for antiproliferative activity in vitro against NCI-H460, HepG2, MCF-7, A2780 and A2780cisR human cancer cell lines. The cytotoxicity data suggest that the H5L1 ligand and [Pt(H3L1)]2, complex 1, may be endowed with important cytotoxic properties since they are capable of not only circumventing cisplatin resistance in A2780cisR but also exhibit antiproliferative activity in NCI-H460. The interactions of these compounds with calf thymus DNA were investigated by UV-vis absorption and a nephrotoxic study, in LLC-PK1 cells, has also been carried out.
- Matesanz, Ana I.,Perles, Josefina,Souza, Pilar
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p. 12538 - 12547
(2013/01/14)
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- Synthesis and structure-activity evaluation of isatin-β- thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing P-glycoprotein
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Cancer multidrug resistance (MDR) mediated by ATP-binding cassette (ABC) transporters presents a significant unresolved clinical challenge. One strategy to resolve MDR is to develop compounds that selectively kill cells overexpressing the efflux transport
- Hall, Matthew D.,Brimacombe, Kyle R.,Varonka, Matthew S.,Pluchino, Kristen M.,Monda, Julie K.,Li, Jiayang,Walsh, Martin J.,Boxer, Matthew B.,Warren, Timothy H.,Fales, Henry M.,Gottesman, Michael M.
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experimental part
p. 5878 - 5889
(2011/10/08)
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- 3-(1,3,4-Thiadiazole-2-yl)quinoline derivatives: Synthesis, characterization and anti-microbial activity
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A new series of thiadiazoles and intermediate thiosemicarbazones were synthesized from the chloroquinone molecule, with an aim to explore their effect on in vitro growth of microorganisms causing microbial infection. The chemical structures of the compound were elucidated by elemental analysis, FTIR, 1H and 13C NMR and ESI-MS spectral data. In vitro anti-microbial activity was performed against Staphylococcusaureus, Streptococcuspyogenes, Salmonellatyphimurium, and Escherichiacoli. The MIC was detected using the double dilution method. The results were compared by calculating percent inhibit area/μg of the compounds and the standard "amoxicillin". The selected compounds were tested for cytotoxic results using MTT assay H9c2 cardiac myoblasts cell line and the results showed that all the compounds offered remarkable >80% viability to a concentration of 200 μg/mL.
- Bhat, Abdul R.,Tazeem,Azam, Amir,Choi, Inho,Athar, Fareeda
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p. 3158 - 3166
(2011/06/26)
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- Anticonvulsant and neurotoxicity evaluation of some novel cyclohexyl-[4-substituted benzylidene/2-oxo-1,2-dihydro-indol-3-ylidene] thiosemicarbazides
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A series of novel cyclohexyl-[4-substituted benzylidene/2-oxo-1,2-dihydro- indol-3-ylidene]thiosemicarbazides were synthesized and screened for anticonvulsant activity in maximal electroshock induced seizure (MES) and subcutaneous metrazol (scMET) induced seizure models in mice. The neurotoxicity was assessed using the rotorod method. The compounds cyclohexyl-[4-(4- chlorophenoxy)- benzylidene]thiosemicarbazide (7d) and cyclohexyl-[2-oxo-1,2- dihydro-indol-3-ylidene]thiosemicarbazide (7i) emerged as the most promising one with anti-MES activity in mice i.p. All the compounds exhibited no neurotoxicity in rotorod method.
- Tripathi, Laxmi,Singh, Ranjit
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experimental part
p. 447 - 450
(2011/11/04)
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- Efficient syntheses of thiadiazole peptides
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Novel N-(Cbz-aminoacyl)thiosemicarbazides 3a-c were cyclized by treatment with sulfuric acid to give 1,3,4-thiadiazoles 4a-c. Compounds 4a-c reacted with N-(Cbz-aminoacyl)- and -dipeptidoylbenzotriazoles to afford chirally pure 1,3,4-thiadiazol-2-yl-subst
- Katritzky, Alan R.,El-Nachef, Claudia,Bajaj, Kiran,Kubik, Jonathan,Haase, Danniebelle N.
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scheme or table
p. 6009 - 6011
(2010/11/16)
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- Structure-activity relationships of mononuclear metal-thiosemicarbazone complexes endowed with potent antiplasmodial and antiamoebic activities
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A useful concept for the rational design of antiparasitic drug candidates is the complexation of bioactive ligands with transition metals. In view of this, an investigation was conducted into a new set of metal complexes as potential antiplasmodium and an
- Bahl, Deepa,Athar, Fareeda,Soares, Milena Botelho Pereira,De Sá, Matheus Santos,Moreira, Diogo Rodrigo Magalh?es,Srivastava, Rajendra Mohan,Leite, Ana Cristina Lima,Azam, Amir
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scheme or table
p. 6857 - 6864
(2010/10/19)
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- Bis-pyrazolines: Synthesis, characterization and antiamoebic activity as inhibitors of growth of Entamoeba histolytica
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The cyclization of chalcone with N-4 substituted thiosemicarbazides under basic condition led to the formation of new compounds, thiocarbamoyl bis-pyrazoline derivatives. The structure of the compounds were elucidated by UV, IR, 1H NMR, 13C NMR and ESI-MS spectral data and thermogravimetric analysis, and their purities were confirmed by elemental analyses. The antiamoebic activity of these complexes was evaluated by microdilution method against HM1:IMSS strain of Entamoeba histolytica and the results were compared with the standard drug, metronidazole. Structure-activity relationship shows that the compound with aromatic substituents at the thiocarbamoyl group was more active than those with the cyclic groups. However, it was clear from the IC50 values that the compounds 15 and 20 are more active and both showed a structural resemblance having an electron withdrawing groups attached to the phenyl ring. MTT assay showed that all the compounds are non-toxic to human kidney epithelial cell line.
- Bhat, Abdul R.,Athar, Fareeda,Azam, Amir
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scheme or table
p. 426 - 431
(2009/04/18)
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- Synthesis and characterization of new thiazolidin-4-one derivatives
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The synthesis of some new functionalized thiazolidin-4-one derivatives has been described. The N-substituted-thiosemicarbazides 3a-3i were obtained though the reaction of alkylamines 2a-2i, carbon disulfide, and hydrazine hydrate. The condensation reaction between 3a-3i and 4-amino-2-methanesulfanylpyrimidine-5- carboxaldehyde 1 afforded the thiosemicarbazones 4a-4i. The corresponding thiazolidin-4-ones 5a-5i were prepared by cyclization of 4a-4i with ethyl bromoacetate. The structures of the final products were confirmed by IR, 1H NMR, 13C NMR, and HRMS.
- Hu, Bao Xiang,Shen, Zhen Lu,Lu, Jun,Hu, Xin Quan,Mo, Wei Min,Sun, Nan,Xu, Dong
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experimental part
p. 523 - 535
(2009/09/25)
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- Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives
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New series of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones 3a-t, 1-methyl-5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones 4a-y and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-thiosemicarbazones 5a-m were synthesized. The structures of the synthesized compounds were confirmed by spectral data and elemental analysis. The new 5-methyl/trifluoromethoxy-1H-indole-2,3-dione derivatives, along with previously synthesized 5-methyl-1H-indole-2,3-dione 3-thiosemicarbazones 6a-l, were evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv. 5-Methyl-1H-indole-2,3-dione 3-thiosemicarbazones (3b, 3d, 3f, 6c, 6d, and 6f), 5-trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones (3q-s) and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-thiosemicarbazones (5e and 5j-l) were found to be the most potent inhibitors of M. tuberculosis growth described in this study.
- Guezel, Oezlen,Karali, Nilguen,Salman, Aydin
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experimental part
p. 8976 - 8987
(2009/04/11)
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- Synthesis and characterization of a new series of hydroxy pyrazolines
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3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one obtained by Claisen-Schmidt condensation of 2-acetyl thiophene with benzaldehyde was converted into 2,3-dibromo-3-phenyl-1-(thiophen-2-yl)propan-1-one, which on treatment with various thiosemicarbazides in the presence of triethylamine in absolute ethanol, yielded the corresponding hydroxy pyrazolines 3a-h. All the compounds were characterized by IR, 1H NMR, and 13C NMR spectra. Copyright Taylor & Francis Group, LLC.
- Parveen, Humaira,Iqbal, Prince Firdoos,Azam, Amir
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experimental part
p. 3973 - 3983
(2009/04/11)
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- Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives
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New series of 5-fluoro-1H-indole-2,3-dione-3-thiosemicarbazones 2a-k and 5-fluoro-1-morpholino/piperidinomethyl-1H-indole-2,3-dione-3-thiosemicarbazones 3a-r were synthesized. The structures of the synthesized compounds were confirmed by spectral data, elemental and single crystal X-ray diffraction analysis. The new 5-fluoro-1H-indole-2,3-dione derivatives, along with previously reported 5-nitro-1H-indole-2,3-dione-3-thiosemicarbazones 2l-v, 1-morpholino/piperidinomethyl-5-nitro-1H-indole-2,3-dione-3-thiosemicarbazones 4a-l, and 5-nitro-1H-indole-2,3-dione-3-[(4-oxo-1,3-thiazolidin-2-ylidene)hydrazones] 5a-s, were evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv. Among the tested compounds, 5-nitro-1H-indole-2,3-dione-3-thiosemicarbazones (2p, 2r, and 2s) and its 1-morpholinomethyl derivatives (4a, 4e, 4g, and 4i) exhibited significant inhibitory activity in the primary screen. The antituberculosis activity of molecules with diverse skeletons was investigated by means of the Electronic-Topological Method (ETM). Ten pharmacophores and ten anti-pharmacophores that have been found by this form the basis of the system capable of predicting the structures of potentially active compounds. The forecasting ability of the system has been tested on structures that differ from those synthesized. The probability of correct identification for active compounds was found as equal to 93% in average. To obtain the algorithmic base for the activity prediction, Artificial Neural Networks were used after the ETM (the so-called combined ETM-ANN method). As the result, only 9 pharmacophores and anti-pharmacophores were chosen as the most important ones for the activity. By this, ANNs classified correctly 94.4%, or 67 compounds from 71.
- Karali, Nilguen,Guersoy, Aysel,Kandemirli, Fatma,Shvets, Nathaly,Kaynak, F. Betuel,Oezbey, Sueheyla,Kovalishyn, Vasyl,Dimoglo, Anatholy
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p. 5888 - 5904
(2008/03/18)
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- Synthesis and antiamoebic activity of 3,7-dimethyl-pyrazolo[3,4-e][1,2,4] triazin-4-yl thiosemicarbazide derivatives
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A series of 3,7-dimethyl-pyrazolo[3,4-e][1,2,4]triazin-4-yl thiosemicarbazide derivatives 3-22 were prepared and evaluated in vitro against HM1:1MSS strain of Entamoeba histolytica, to identify the compounds for antiamoebic activity. They exhibited antiamoebic activity in the range (IC 50 = 0.81-7.31 μM). The results were compared to the activity of known drug metronidazole. It is inferred from the in vitro studies that the compounds 10, 11, 17 and 18 were found to be significantly better inhibitors of E. histolytica since IC50 values in the μM range elicited by these compounds are much lower than metronidazole. Besides, compounds 11 and 17 have shown the most promising antiamoebic activity (IC50 = 0.81 μM of 11, IC50 = 0.84 μM of 17 versus IC50 = 1.81 μM of metronidazole). The study suggests the possibility of developing triazine analogues as potential drug candidates for antiamoebic activity.
- Singh, Shailendra,Husain, Kakul,Athar, Fareeda,Azam, Amir
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p. 255 - 262
(2007/10/03)
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- Synthesis and antitumor activity of new thiosemicarbazones of 2-acetylimidazo[4,5-b]pyridine
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A number of thiosemicarbazones of 2-acetyl-imidazo[4,5-b]pyridine were prepared in order to investigate their in vitro antineoplastic activities. Three compounds: (i) 2-acetylimidazo[4,5-b]pyridin-4-tert-butyl-3-thiosemicarbazone [(A7), NSC674098], (ii) 2-acetylimidazo[4,5-e]pyridin-4-tert-butyl-3- thiosemicarbazone [(A9), NSC674099], (iii) 2-acetylimidazo[4,5-i] pyridin-4-cyclohexyl-3-thiosemicarbozone [(A11), NSC674101] showed remarkable activity against some of the cell lines tested. The Biological Evaluation Committee of N.C.I, determined that further secondary testing should be carried out (these compounds were tested against prostate cancer).
- Mylonas, Stavros,Mamalis, Athanasios
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p. 1273 - 1281
(2007/10/03)
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- Discovery of thiadiazoles as a novel structural class of potent and selective PDE7 inhibitors. Part 1: Design, synthesis and structure-activity relationship studies
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The synthesis and SAR studies of a series of structurally novel small molecule inhibitors of PDE7 are discussed. The best compounds from the series displayed low nanomolar inhibitory activity and are selective versus PDE4.
- Vergne, Fabrice,Bernardelli, Patrick,Lorthiois, Edwige,Pham, Nga,Proust, Emmanuelle,Oliveira, Chrystelle,Mafroud, Abdel-Kader,Royer, Frederique,Wrigglesworth, Roger,Schellhaas, Jennifer,Barvian, Mark,Moreau, Fran?ois,Idrissi, Moulay,Tertre, Anita,Bertin, Bernadette,Coupe, Magali,Berna, Patrick,Soulard, Patricia
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p. 4607 - 4613
(2007/10/03)
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