- Synthesis and Antimicrobial Evaluation of Novel Derivatives of Semicarbazide and 1,2,4-triazole
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Reaction of phenoxyacetic acid hydrazide with isocyanate was used to the synthesis of new semicarbazide derivatives. Cyclization of these compounds in a 2% aqueous solution of sodium hydroxide led to formation of 1,2,4-triazole-3-one. The chemical structure of synthesized compounds was confirmed by elemental analysis and spectroscopic methods (1H and 13C NMR). On the basis of the NMR, spectra were found that cyclic compounds 1,2,4-triazole exist in the -one form. Moreover, all derivatives were examined for their in vitro activity against some species of bacteria. New compounds presented mild or moderate antimicrobial activity only against reference Gram-positive bacteria. Two derivatives (one semicarbazide and one triazole) showed bactericidal or bacteriostatic activity.
- Pachuta-Stec, Anna,Biernasiuk, Anna,Malm, Anna,Pitucha, Monika
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Read Online
- Anion sensing using colorimetric amidourea based receptors incorporated into a 1,3-disubstituted calix[4]arene
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The synthesis of amidourea-based colorimetric anion sensors 1 and 2 and the evaluation of these sensors using anions such as acetate (CH3 CO2-), fluoride (F-), hydrogen phosphate (H2 PO4su
- Quinlan, Eoin,Matthews, Susan E.,Gunnlaugsson, Thorfinnur
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Read Online
- Novel phenolic Mannich base derivatives: synthesis, bioactivity, molecular docking, and ADME-Tox Studies
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In this study, it was aimed to synthesize novel molecules containing potential biological active phenolic Mannich base moiety and evaluate the inhibition properties against α-glycosidase (α-Gly) and acetylcholinesterase (AChE). For this purpose, phenolic aldehydes (1–3) were synthesized from 4-hydroxy-3-methoxy benzaldehyde (vanillin) according to the Mannich Reaction. Five different carboxylic acid hydrazides (4a-e) were synthesized from esters obtained from carboxylic acids. Fifteen Schiff base derivatives (5a-e, 6a-e, and 7a-e) were synthesized from the condensation reaction of compounds 1–3 with 4a-e. In this work, a series of novel Schiff bases from Phenolic Mannich bases (5a-e, 6a-e, and 7a-e) were tested toward α-Gly and AChE enzymes. Compounds 5a-e, 6a-e, and 7a-e showed Kis in ranging of 341.36 ± 31.84–904.76 ± 93.56?nM on AChE and 176.27 ± 22.87—621.77 ± 69.98?nM on α-glycosidase. Finally, novel compounds were found using molecular docking method to calculate the biological activity of these bases against many enzymes. The enzymes used in these calculations are acetylcholinesterase and α-glycosidase, respectively. Molecule 6b is more effective and active than other molecules with a docking score parameter value of ? 8.77 against AChE enzyme and 6d is more effective and active than other molecules with a docking score parameter value of ? 4.94 against α-Gly enzyme. After calculating the biological activities of novel compounds, ADME/T analysis parameters were examined to calculate the future drug use properties.
- Tokal?, Feyzi Sinan,Taslimi, Parham,Demircio?lu, ?brahim Hakk?,?endil, K?v?lc?m,Tuzun, Burak,Gül?in, ?lhami
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p. 563 - 577
(2021/07/12)
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- Identification and synthesis of selective cholesterol esterase inhibitor using dynamic combinatorial chemistry
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In this study, the concept of dynamic combinatorial chemistry (DCC) was applied to explore novel cholesterol esterase (CEase) inhibitors. In the presence of enzyme, two substrates (A1H3 and A2H3) were amplified from the dynamic combinatorial library (DCL), which was generated through reversible acylhydrazone formation reaction. In the in vitro biological evaluation, compound A1H3 exhibited not only potent (IC50 in nanomolar range) but also selective inhibition (>120 folds of selectivity for CEase over AChE). Furthermore, the binding pattern and possible binding mechanism were investigated in the kinetic experiment and molecular docking study, respectively.
- Zhao, Shuang,Wu, Yao,Hu, Lei
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- Phenoxyacetohydrazones against Trypanosoma cruzi
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Herein, we reported the design, synthesis, antitrypanosomal and cytotoxic evaluation of a new phenoxyacetohydrazones series. All derivatives were assayed against bloodstream trypomastigote forms of T. cruzi (Y strain) and intracellular amastigotes using the model of L-929 cells infected with trypomastigotes of the Tulahuen strain. Compound (E)-N′-(3.4-dihydroxybenzylidene)-2-phenoxyacetohydrazide (11) showed activity against trypomastigotes (IC50/24 h = 10.3 μM) equivalent to that of benznidazole and with selectivity index (SI) = 46. Against infected cultures, (E)-N′-((5-nitrofuran-2-yl) methylene)-2-phenoxyacetohydrazide (19) was active at the nanomolar range (IC50/96 h = 40 nM), being about 38-fold more active than the standard drug and with SI equal to 2500. Thus, derivatives 11 and 19 could be considered a good prototypes for the development of new candidates for Chagas disease therapy. [Figure not available: see fulltext.]
- Barbosa, Juliana M. C.,Capelini, Camila,Carvalho, Samir A.,Murta, Silvane M. F.,Sales Junior, Policarpo A.,Salom?o, Kelly,Wardell, James L.,Wardell, Solange M. S. V.,da Silva, Edson F.,de Souza, Kátia R.
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p. 1703 - 1712
(2021/08/03)
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- N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides
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A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.
- Manoj Kumar, Mesram,Venkataramana, Parikibanda,Yadagiri Swamy, Parikibanda,Chityala, Yadaiah
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supporting information
p. 17713 - 17721
(2021/11/10)
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- Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment
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Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.
- Chai, Jianqi,Chen, Min,Jin, Fei,Kong, Xiangyi,Wang, Xiaobin,Xue, Wei,Yang, Chunlong
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- Host-guest complexation between simple pillar[5]arene and a new type of neutral guests
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Pillar[5]arenes are a new type of supramolecular hosts constructed from hydroquinone and their derivatives linked by methylene units. Searching new host-guest interaction between pillar[5]arenes and neutral guests are thus great interesting. Here, four neutral guests (AA0, AA2, AA4 and AA6) with both amino and amide groups were prepared from phenol by two steps. The host-guest interactions between perethylated pillar[5]arene (EtP5) and guest molecules were investigated in detail by various technologies, including 1H NMR, 13C NMR, 2D NOESY NMR, MS analysis and DFT calculation. We found that the guests (AA4 and AA6) with longer alkyl chain can form a stable inclusion complex with EtP5 through C–H···O, N–H···O, C–H···N and C–H···π interactions while shorter guests (AA0 and AA2) could not.
- Yan, Xin,Guo, Hao,Cen, Moupan,Huang, Youyou,Zhou, Lin,Zhu, Guohua,Yao, Yong
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p. 614 - 619
(2021/02/05)
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- Identification of a Novel Oxadiazole Inhibitor of Mammalian Target of Rapamycin
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We performed a biochemical screen against mTOR using in-house small molecule library. Two novel, structurally distinct hits were identified. Among them, a novel oxadiazole scaffold compound (2) suppressed the phosphorylation of both S6K1 and Akt1 in HeLa cells. Docking study suggested that 2 is ATP-competitive and shows a pi-pi interaction with Trp2239 and hydrogen bonds with Trp2239 and Thr2245. Through derivatization, a slightly more potent analogue (2a) was identified with IC50 of 9.6 μM. Our study provides a starting point for discovery of novel potent mTOR inhibitors.
- Lim, Sunwoo,Lee, Hyomin,Kim, Euijung,Hur, Wooyoung
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p. 296 - 303
(2020/02/04)
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- Synthesis and anti-coronavirus activity of a series of 1-thia-4-azaspiro[4.5]decan-3-one derivatives
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A series of 1-thia-4-azaspiro[4.5]decan-3-ones bearing an amide group at C-4 and various substitutions at C-2 and C-8 were synthesized and evaluated against human coronavirus and influenza virus. Compounds 7m, 7n, 8k, 8l, 8m, 8n, and 8p were found to inhibit human coronavirus 229E replication. The most active compound was N-(2-methyl-8-tert-butyl-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl)-3-phenylpropanamide (8n), with an EC50 value of 5.5 μM, comparable to the known coronavirus inhibitor, (Z)-N-[3-[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]-3-oxo-1-phenylprop-1-en-2-yl]benzamide (K22). Compound 8n and structural analogs were devoid of anti-influenza virus activity, although their scaffold is shared with a previously discovered class of H3 hemagglutinin-specific influenza virus fusion inhibitors. These findings point to the 1-thia-4-azaspiro[4.5]decan-3-one scaffold as a versatile chemical structure with high relevance for antiviral drug development.
- Apayd?n, ?a?la Begüm,Cesur, Nesrin,Stevaert, Annelies,Naesens, Lieve,Cesur, Zafer
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- Synthesis and larvicidal activity of 1,3,4-oxadiazole derivatives containing a 3-chloropyridin-2-yl-1H-pyrazole scaffold
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Abstract: A new series of 1,3,4-oxadiazole derivatives with a 3-chloropyridin-2-yl-1H-pyrazole moiety was designed, synthesized, and characterized. The results of bioassay against Helicoverpa armigera and Plutella xylostella indicated that some of the synthesized compounds showed remarkable larvicidal activity. In particular, the LC50 values of the most active compounds against P. xylostella were 46.5, 23.9, and 13.9?mg/dm3, and against Helicoverpa armigera were 88.3 and 69.5?mg/dm3, the latter being slightly better than commercial chlorpyrifos (LC50 103.77?mg/dm3). Preliminary SAR was also discussed. Graphical abstract: [Figure not available: see fulltext.].
- Wang, Yanyan,Lu, Xiumian,Shi, Jun,Xu, Jiahong,Wang, Fenghua,Yang, Xiao,Yu, Gang,Liu, Zhiqian,Li, Chuanhui,Dai, Ali,Zhao, Yonghui,Wu, Jian
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p. 611 - 623
(2018/01/17)
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- Synthesis and luminescence properties of novel 8-hydroxyquinoline derivatives and their Eu(III) complexes
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Six novel 8-hydroxyquinoline derivatives were synthesized using 2-methyl-8-hydroxyquinoline and para-substituted phenol as the main starting materials, and were characterized by 1H nuclear magnetic resonance (NMR), mass spectrometry (MS), ultraviolet (UV) light analysis and infra-red (IR) light analysis. Their complexes with Eu(III) were also prepared and characterized by elemental analysis, molar conductivity, UV light analysis, IR light analysis, and thermogravimetric–differential thermal analysis (TG–DTA). The results showed that the ligand coordinated well with Eu(III) ions and had excellent thermal stability. The structure of the target complex was EuY1–6(NO3)3.2H2O. The luminescence properties of the target complexes were investigated, the results indicated that all target complexes had favorable luminescence properties and that the introduction of an electron-donating group could enhance the luminescence intensity of the corresponding complexes, but the addition of an electron-withdrawing group had the opposite effect. Among all the target complexes, the methoxy-substituted complex (–OCH3) had the highest fluorescence intensity and the nitro-substituted complex (–NO2) had the weakest fluorescence intensity. The results showed that 8-hydroxyquinoline derivatives had good energy transfer efficiency for the Eu(III) ion. All the target complexes had a relatively high fluorescence quantum yield. The fluorescence quantum yield of the complex EuY3(NO3)3.2H2O was highest among all target complexes and was up to 0.628. Because of excellent luminescence properties and thermal stabilities of the Eu(III) complexes, they could be used as promising candidate luminescent materials.
- Wu, Yongqiang,Guo, Tiantong,Shu, Dehua,Zhang, Wu,Luan, Fangfei,Shi, Ling,Guo, Dongcai
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p. 855 - 862
(2018/07/13)
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- Tirfluoromethylpyridine oxadiazoles (ether)derivative and application thereof
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The invention discloses an application of a tirfluoromethylpyridine oxadiazole (ether)derivative in a pesticide. A structure is shown as a general formula I, a compound shown in the general formula Ihas good insecticidal activity, and can be used for controlling insects such as diamondback moth and armyworm. The compound has excellent control effect for insects such as diamondback moth and armyworm, and also has control effect for the insects having resistance to the traditional pesticides, in addition, introduction of fluorine-containing groups such as tirfluoromethylpyridine and oxadiazoleas well as heterocyclic ring can enhance a rate for forming hydrogen bond effect between a compound and a target, and the activity of the compound is increased.
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- Synthesis, Nematicidal Activity, and 3D-QSAR of Novel 1,3,4-Oxadiazole/ Thiadiazole Thioether Derivatives
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Forty one novel 1,3,4-oxadiazole/thiadiazole thioether derivatives containing phenoxy moiety were designed and synthesized. Bioassay demonstrated that some of them showed remarkable activities against Tylenchulus semipenetrans in vitro and in vivo. Compounds 20, 21, 35 and 39 showed excellent lethal activities after treatment for 48?h in vitro, with LC50 values of 13.4?±?1.8, 11.7?±?2.5, 13.7?±?2.4 and 13.3?±?1.1?mg·L–1, respectively, which were obviously superior to fosthiazate (49.1?±?2.8?mg·L–1) and avermectin (26.6?±?2.3?mg·L–1). Compound 21 can effectively control the citrus nematode disease caused by T. semipenetrans at 200?mg·L–1 in vivo with (68?±?3)% inhibitory effect, which was even better than that of avermectin ((63?±?2)%). The CoMFA and CoMSIA models of three-dimensional quantitative structure-activity relationships (3D-QSARs) were established. The compound 33 was designed based on the 3D-QSAR models with more vigorous nematicidal activities in vitro (LC50?=?9.8?±?1.4?mg·L–1) and in vivo ((70?±?5)%). These results demonstrated that compound 33 can be considered as a potential nematicide.
- Chen, Jixiang,Gan, Xiuhai,Yi, Chongfen,Wang, Shaobo,Yang, Yuyuan,He, Fangcheng,Hu, Deyu,Song, Baoan
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p. 939 - 944
(2018/09/22)
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- 1,2,4-Triazole-based benzothiazole/benzoxazole derivatives: Design, synthesis, p38α MAP kinase inhibition, anti-inflammatory activity and molecular docking studies
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Novel N-(benzothiazol/oxazol-2-yl)-2-[(5-(phenoxymethyl)-4-aryl-4H-1,2,4-triazol-3-yl)thio] acetamide derivatives (5a-n) were synthesized and investigated for in vitro anti-inflammatory activity and p38α MAP kinase inhibition. Compounds showing good in vitro activities (5a, 5b, 5d, 5e, 5i, 5k and 5l) were studied for their in vivo anti-inflammatory activity using carrageenan induced rat paw edema model. Compound 5b emerged as the most active compound with an edema inhibition of 84.43%. It also showed improved GI safety profile with lower ulcer severity index and lipid peroxidation potential. Also, p38α MAP kinase assay of 5b showed superior inhibitory potency (IC50:0.031 ± 0.14 μM) than the standard SB 203580 (IC50:0.043 ± 0.14 μM). To predict their binding mode compounds were also docked against p38α MAP kinase enzyme. Compound 5b and SB 203580 showed hinge region interaction with MET 109.
- Tariq, Sana,Kamboj, Payal,Alam, Ozair,Amir, Mohd.
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p. 630 - 641
(2018/09/29)
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- Synthesis and antibacterial evaluation of new sulfone derivatives containing 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole moiety
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Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds 5I-1-5I-7 exerted remarkably higher activities with EC50 values ranging from 0.45-1.86 μg/mL against X. oryzae and 1.97-20.15 μg/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with protective effect of 90.4%, 77.7%, and 81.1% at 200 μg/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases.
- Su, Shihu,Zhou, Xia,Liao, Guoping,Qi, Puying,Jin, Linhong
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- 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives as well as preparation method and application thereof
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The invention discloses 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives as well as a preparation method and an application thereof. The 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives have the general formula (I) shown in the following specification, wherein R1 represents as 4-chlorphenyl, 4-fluorophenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-cyano-3,5-difluorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 4-t-butylphenyl, 2-fluorophenyl and other substituents; R2 represents methyl, ethyl, 4-chlorobenzyl, 2,4-dichlorobenzyl, 4-trifluoromethoxy, benzyl, 4-fluorobenzyl, 4-chlorobenzyl and other substituents; X represents O or S. The compound can be used as a pesticide for killing crop nematode and inhibiting bacterial diseases of crops.
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Paragraph 0032
(2017/04/03)
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- Synthesis of acylhydrazines and, symmetrical and asymmetrical diacylhydrazines from carboxylic acid via the Vilsmeier reagent mediated process
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(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent) has been used as an efficient and convenient reagent for the one-pot synthesis of acylhydrazines and symmetrical and asymmetrical diacylhydrazines from carboxylic acids. This reaction proceeded smoothly under mild conditions and it is quite practical, since the starting carboxylic acids can be easily handled and stored. Cleanliness, simplicity of the method and good to excellent yield of products are other advantages of this method.
- Zarei, Maaroof,Nakhli, Maliheh Eslami
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p. 1909 - 1918
(2017/02/15)
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- One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent
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A simple and efficient synthetic method for the one-pot synthesis of 1,3,4-thiadiazoles utilizing Vilsmeier reagent was developed. In this method carboxylic acids and hydrazine were converted to 1,3,4-thiadiazoles in the presence of Vilsmeier reagent and Lawesson's reagent. The influence of the thionation reagent, solvent, temperature and time, in this reaction was discussed. The developed methodology for 1,3,4-thiadiazole synthesis has the advantage of simplicity, ambient reaction conditions, easy purification and good to excellent yield of products.
- Zarei, Maaroof
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p. 1867 - 1872
(2017/03/11)
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- Dibenzo-azepine-dione anti-tumor compounds and preparation method thereof
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The invention provides dibenzo-azepine-dione anti-tumor compounds and a preparation method thereof, belongs to the technical field of medicines and particularly relates to compounds with specific chemical structures with anti-tumor activity. General formulae of the compounds include a general formula I, a general formula II, a general formula III and a general formula IV. The invention further provides an application of the compounds in anti-tumor and the preparation method. Tests of various tumor cell lines such as human lung cancer cells and human gastric carcinoma cells prove that the compounds have the tumor activity inhibition effect. The raw materials of the compounds are easily available, the preparation method is simple, and experiments prove that the compounds have good anti-cancer effect and have good application prospect in the field of design, research and development of anti-tumor drugs.
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Paragraph 0119; 0122; 0123
(2016/10/07)
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- Synthesis, Characterization and Properties of Novel Coumarin Derivatives and Their Europium Complexes
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Seven novel coumarin derivatives derived from salicylaldehyde and phenol were synthesized and characterized by 1H NMR and 13C NMR spectra, mass spectra, infrared spectra and elemental analysis. Their corresponding Eu(III) complexes having general formula EuL1-7(NO3)3·2H2O were successfully prepared and characterized by elemental analysis, EDTA titrimetric, molar conductivity, UV-Vis, FT-IR and thermal performance studies. The luminescence properties, fluorescence quantum yields and the electrochemical properties of the title complexes were investigated. The results showed that the title complexes exhibited characteristic emissions of europium ions and possessed relatively good fluorescence quantum yields. The luminescence intensity of the complex with bromine-substituted group is the strongest among all the title complexes. The introduction of electron-withdrawing groups can increase the luminescence properties and fluorescence quantum yields, decrease the HOMO and LUMO energy levels of the title europium complexes, but electron-withdrawing group conversely. And these title complexes may possibly be useful for studying in luminescent materials field.
- Yan, Dong,Li, Dong,Cheng, Guang,Yang, Zehui,Shi, Ling,Guo, Dongcai
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p. 849 - 859
(2015/08/24)
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- Synthesis and luminescence properties of pyrazolone derivatives and their terbium complexes
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Seven novel pyrazolone derivatives were synthesized and characterized by 1H NMR and 13C NMR spectra, mass spectra, infrared spectra and elemental analysis. Their terbium complexes were prepared and characterized by elemental analysis, EDTA titrimetric analysis, UV/vis spectra, infrared spectra and molar conductivity, as well as thermal analysis. The fluorescence properties and fluorescence quantum yields of the complexes were investigated at room temperature. The results indicated that pyrazolone derivatives had good energy-transfer efficiency for the terbium ion. All the terbium complexes emitted green fluorescence characteristic of terbium ions, possessed strong fluorescence intensity, and showed relatively high fluorescence quantum yields. Cyclic voltammograms of the terbium complexes were studied and the highest occupied molecular orbital (HOMO) and lowest occupied molecular orbital (LUMO) energy levels of these complexes were estimated.
- Xiao, Haihua,Jiang, Xi,Li, Dong,Wu, Limin,Zhang, Wu,Guo, Dongcai
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p. 677 - 685
(2015/12/04)
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- Novel hybrid-pyrrole derivatives: Their synthesis, antitubercular evaluation and docking studies
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Using novel hybrid molecules for the treatment of tuberculosis is one of the latest approaches. Keeping this concept in mind, thirty two hybrid compounds were synthesized, with pyrrole as one of the moieties, clubbed to coumarin, ibuprofen and isoniazid. The compounds were evaluated against Mycobacterium tuberculosis H37Rv strain. Compounds 7e and 8e exhibited MIC of 3.7 and 5.10 μg mL-1 and growth inhibition of 95% and 92%, respectively. These compounds were also active against single drug resistant bacterial strains. The compounds were devoid of cytotoxicity when tested against Vero African green monkey kidney cell line. Docking study was carried out on enoyl acyl carrier protein enzyme to provide some understanding into the mechanism of action of these compounds.
- Saha, Rikta,Alam, Md. Mumtaz,Akhter, Mymoona
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p. 12807 - 12820
(2015/02/19)
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- Synthesis, antiproliferative activity, and molecular docking studies of curcumin analogues bearing pyrazole ring
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Several curcumin analogues bearing pyrazole were synthesized and characterized by IR, NMR, and mass spectral data. There were four tested compounds among 11 synthesized compounds, which were evaluated for antiproliferative activity and showed significant activity in both one-dose and five-dose assays. The antiproliferative effects were tested on a panel of 60 cell lines, according to the National Cancer Institute screening protocol. The most active compounds among the series were 3,5-bis(4-hydroxy-3-methylstyryl)-1H-pyrazole-1-carboxamide (3k) which showed mean percent growth inhibition of 116.09 in one-dose assay at 10 μM, and GI50 values were ranging between 0.0912 and 2.36 μM in five-dose assay. The best results were recorded on the leukaemia cell lines with value ranging from 0.0912 to 0.365 μM. All the tested compounds showed broad-spectrum antiproliferative activity over different cancer cell lines. When compared with the standard drug paclitaxel, the compound 3k showed superior activity on nearly 42 cell lines. The molecular docking study was performed to explore the binding interaction of these curcumin analogues with the active site of EGFR tyrosine kinase (EGFR-TK). The hydroxyl group of both phenyl rings was important for the rein-geminated hydrogen bonding by either side chain or backbone with the active site of EGFR-TK. Graphical Abstract: Four curcumin analogues were evaluated for their antiproliferative activity and showed promising results. The molecular docking studies showed that all the compounds (3a-k) were well accommodated in the EGFR tyrosine kinase.[Figure not available: see fulltext.]
- Ahsan, Mohamed Jawed,Choudhary, Kavita,Jadav, Surender Singh,Yasmin, Sabina,Ansari, Md. Yousuf,Sreenivasulu, Reddymasu
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p. 4166 - 4180
(2015/11/02)
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- Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents
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In order to develop a lead antimycobacterium tuberculosis compound, a series of 52, novel pyrrole hydrazine derivatives have been synthesized and screened which target the essential enoyl-ACP reductase. The binding mode of the compounds at the active site of enoyl-ACP reductase was explored using surflex-docking method. The binding model suggests one or two hydrogen bonding interactions between pyrrole hydrazones and InhA enzyme. Highly active compound 5r (MIC 0.2 μg/mL) showed hydrogen bonding interactions with Tyr158 and NAD+ in the same manner as those of ligands PT70 and triclosan. The CoMFA and CoMSIA models generated with database alignment were the best in terms of overall statistics. The predictive ability of the CoMFA and CoMSIA models was determined using a test set of 13 compounds, which gave predictive correlation coefficients (rpred2) of 0.896 and 0.930, respectively.
- More, Uttam A.,Joshi, Shrinivas D.,Aminabhavi, Tejraj M.,Gadad, Andanappa K.,Nadagouda, Mallikarjuna N.,Kulkarni, Venkatrao H.
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p. 199 - 218
(2014/01/06)
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- Anthelmintic evaluation of some novel synthesized 1,2,4-triazole moiety clubbed with benzimidazole ring
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A series of N-[3-{(1H-benzo[d]imidazol-2-ylthio) methyl}-5-mercapto-4H-1,2, 4-triazol-4-yl]-2-substituted phenoxy acetamide 6(a-g) were synthesized by the mixture of the compound of potassium 2-(2-(1H-benzo[d]imidazol-2-ylthio) acetyl) hydrazinecarbodithioate (4) and arytoxy acid hydrazide (5) in presence of hydrochloric acid. The predicted structures of the synthesized compounds were confirmed by different spectral analysis studies. The title compounds 6(a-g) were screened for anthelmintic activity against Pheretima posthumous. The entire compounds were exhibited good anthelmintic activity when compared with standard drugs such as Albendazole and Piperazine.
- Kumar, P. Sudhir,Sahoo
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p. 211 - 217
(2014/06/23)
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- Synthesis, antibacterial and anticancer evaluation of 5-substituted (1,3,4-oxadiazol-2-yl)quinoline
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2-Chloroquinoline-3-carbaldehyde (2) was synthesized via Vilsmeier-Haack method using acetanilide. Phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1H-benzimidazol-1-yl)acetohydrazide (7a-c) were synthesized using 2-[2-(phenoxy/naphthalen-1-yl/naphthalen-2-yloxy methyl)-1H-benzimidazol-1-yl]acetohydrazide (6a-c). The title compounds 2-chloro-3-{5-[(2-phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1-H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-yl}quinolone (8a-c) were prepared using chloramine-T. In the second series, (2-chloroquinolin-3-yl)methylidene]-substituted benzohydrazide (11a-i) were prepared by the reaction of 2-chloroquinoline-3-carbaldehyde (2) and an acid hydrazide (10a-i). The synthesized compounds were characterized by IR, NMR, Mass spectrometry, elemental analysis and screened for their antibacterial (serial dilution technique and disc diffusion method) and anticancer activity by NCI 60 cell screen at a single high dose (10-5 M) on various panel/cell lines. The synthesized compounds (8a, 8c, 12a, 12b, 12c and 12h) were acting as a magic bullet against gram-positive strains of Bacillus cereus MTCC1305, and the compounds (12a, 12c and 12h) were also found to be extremely active against Klebsiella pneumonia NCTC7447. In the in vitro screen on tested cancer cell line, the compound (12d) showed 95.70 growth percent (GP) and highly active on SNB-75 (CNS cancer) and UO-31 (renal cancer) (GP = 53.35 and 64.35, respectively), and the compound (8a) showed 96.86 GP and highly active on SNB-75 (CNS cancer GP 51.27).
- Salahuddin,Mazumder, Avijit,Shaharyar, Mohammad
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p. 2514 - 2528
(2015/02/19)
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- Alkylsulfanyl-1,2,4-triazoles, a New Class of allosteric valosine containing protein inhibitors. Synthesis and structure-activity relationships
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Valosine containing protein (VCP), also known as p97, is a member of AAA ATPase family that is involved in several biological processes and plays a central role in the ubiquitin-mediated degradation of misfolded proteins. VCP is an ubiquitously expressed, highly abundant protein and has been found overexpressed in many tumor types, sometimes associated with poor prognosis. In this respect, VCP has recently received a great deal of attention as a potential new target for cancer therapy. In this paper, the discovery and structure-activity relationships of alkylsulfanyl-1,2,4-triazoles, a new class of potent, allosteric VCP inhibitors, are described. Medicinal chemistry manipulation of compound 1, identified via HTS, led to the discovery of potent and selective inhibitors with submicromolar activity in cells and clear mechanism of action at consistent doses. This represents a first step toward a new class of potential anticancer agents.
- Polucci, Paolo,Magnaghi, Paola,Angiolini, Mauro,Asa, Daniela,Avanzi, Nilla,Badari, Alessandra,Bertrand, Jay,Casale, Elena,Cauteruccio, Silvia,Cirla, Alessandra,Cozzi, Liviana,Galvani, Arturo,Jackson, Peter K.,Liu, Yichin,Magnuson, Steven,Malgesini, Beatrice,Nuvoloni, Stefano,Orrenius, Christian,Sirtori, Federico Riccardi,Riceputi, Laura,Rizzi, Simona,Trucchi, Beatrice,O'Brien, Tom,Isacchi, Antonella,Donati, Daniele,D'Alessio, Roberto
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p. 437 - 450
(2013/04/10)
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- Aggrecanase-2 inhibitors based on the acylthiosemicarbazide zinc-binding group
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Osteoarthritis is a disabling disease characterized by the articular cartilage breakdown. Aggrecanases are potential therapeutic targets for the treatment of this pathology. At the starting point of this project, an acylthiosemicarbazide was discovered to inhibit aggrecanase-2. The acylthiosemicarbazide Zn binding group is also a convenient linker for library synthesis. A focused library of 920 analogs was thus prepared and screened to establish structure-activity relationships. The modification of the acylthiosemicarbazide was also explored. This strategy combining library design and discrete compounds synthesis yielded inhibitor 35, that is highly selective for aggrecanases over a panel of metalloproteases and inhibits the degradation of native fully glycosylated aggrecan. A docking study generated binding conformations explaining the structure-activity relationships.
- Maingot, Lucie,Elbakali, Jamal,Dumont, Julie,Bosc, Damien,Cousaert, Nicolas,Urban, Agathe,Deglane, Gaelle,Villoutreix, Bruno,Nagase, Hideaki,Sperandio, Olivier,Leroux, Florence,Deprez, Benoit,Deprez-Poulain, Rebecca
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p. 244 - 261
(2013/10/01)
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- Regioselective sy nthesis and antimicrobial evaluation of new 1-aryloxyacetyl-, 1-thiophenoxyacetyl- and 1-phenylaminoacetylsubstituted 3-alkyl(aryl/heteroaryl)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles
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This paper describes an efficient approach for the regioselective synthesis of new series of twenty 1-aryloxy(thio)acetyl and 1-(phenylamino)acetyl- substituted 5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles (3) in 34-96% yields from the cyclocondensation reaction of 4-alkoxy-4-alkyl-(aryl/heteroaryl) -1,1,1-trifluoroalk-3-en-2-ones with different substituted acetohydrazides. Dehydration reactions of 3, carried out in the presence of thionyl chloride, furnished two examples of aromatic 5-trifluoromethyl-1H-pyrazole derivatives, in 78-82% yields. From antimicrobial tests the fungi C. albicans proved to be particularly susceptible to the action of 1-(phenylamino)acetyl-substituted 3-alkyl-2-pyrazoline derivatives; however the first results are still weak when compared to standard drugs. ARKAT-USA, Inc.
- Bonacorso, Helio G.,Pittaluga, Everton P.,Alves, Sydney H.,Schaffer, Larissa F.,Cavinatto, Susiane,Porte, Liliane M. F.,Paim, Gisele R.,Martins, Marcos A. P.,Zanatta, Nilo
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- Pharmacological screening for anti-inflammatory, analgesic activity of pyrazolyl derivatives along with molecular docking studies
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The pyrazole derivatives were synthesized and pharmacologically evaluated for analgesic (tail flick) and anti-inflammatory (based on carrageenan-induced paw edema) activities. Compound 4k showed high potency as an anti-inflammatory agent after 3 and 4-h time intervals (P0.001) equipotent to indomethacin. They were devoid of ulcerogenic potential when administered at a dose of 30 mg/kg. The compounds, which showed less ulcerogenic action, also showed reduced malondialdehyde content (MDA), which is one of the byproduct of lipid peroxidation. Further docking studies of titled compounds was done to understand key interactions responsible for observed inhibition of COX enzyme. The most active compound 4k was found to have -11.192 kcal/mol, as the free energy of binding. Various other key interactions between the synthesized molecules and active site of COX-2 enzyme, responsible for the obtained pharmacological results were also reported. Most of the active compounds were docked well into the active sites of the receptor. Springer Science+Business Media, LLC 2011.
- Kaushik, Darpan,Kumar, Rajnish,Khan, Suroor Ahmed,Chawla, Gita
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p. 3646 - 3655
(2013/02/23)
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- Synthesis and xanthine oxidase inhibitory activity of 7-methyl-2- (phenoxymethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives
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An elevated level of blood uric acid (hyperuricemia) is the underlying cause of gout. Xanthine oxidase is the key enzyme that catalyzes the oxidation of hypoxanthine to xanthine and then to uric acid. Allopurinol, a widely used xanthine oxidase inhibitor is the most commonly used drug to treat gout. However, a small but significant portion of the population suffers from adverse effects of allopurinol that includes gastrointestinal upset, skin rashes and hypersensitivity reactions. Moreover, an elevated level of uric acid is considered as an independent risk factor for cardiovascular diseases. Therefore use of allopurinol-like drugs with minimum side effects is the ideal drug of choice against gout. In this study, we report the synthesis of a series of pyrimidin-5-one analogues as effective and a new class of xanthine oxidase inhibitors. All the synthesized pyrimidin-5-one analogues are characterized by spectroscopic techniques and elemental analysis. Four (6a, 6b, 6d and 6f) out of 20 synthesized molecules in this class showed good inhibition against three different sources of xanthine oxidase, which were more potent than allopurinol based on their respective IC50 values. Molecular modeling and docking studies revealed that the molecule 6a has very good interactions with the Molybdenum-Oxygen-Sulfur (MOS) complex a key component in xanthine oxidase. These results highlight the identification of a new class of xanthine oxidase inhibitors that have potential to be more efficacious, than allopurinol, to treat gout and possibly against cardiovascular diseases.
- Sathisha,Khanum, Shaukath A.,Chandra, J.N. Narendra Sharath,Ayisha,Balaji,Marathe, Gopal K.,Gopal, Shubha,Rangappa
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p. 211 - 220
(2011/03/17)
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- Molecular properties prediction and synthesis of novel 1,3,4-oxadiazole analogues as potent antimicrobial and antitubercular agents
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In the present investigation, a series of 1,5-dimethyl-2-phenyl-4-{[(5- aryl-1,3,4-oxadiazol-2-yl)methyl]amino}-1,2-dihydro-3H-pyrazol-3-one were subjected to molecular properties prediction, drug-likeness by Molinspiration (Molinspiration, 2008) and MolSoft (MolSoft, 2007) software, lipophilicity and solubility parameters using ALOGPS 2.1 program. The compounds followed the Lipinski 'Rule of five' were synthesized for antimicrobial and antitubercular screening as oral bioavailable drugs/leads. Maximum drug-likeness model score (0.95) was found for compound, 4a. All the synthesized compounds were characterized by IR, NMR and mass spectral analysis followed by antimicrobial and antimycobacterial screening. Among the title compounds, compound 4d showed pronounced activity against Mycobacterium tuberculosis H37Rv and isoniazid resistant M. tuberculosis (INHR-TB) with minimum inhibitory concentrations (MICs) 0.78 μM and 1.52 μM, respectively. The compound, 4a showed maximum activity against all bacterial strains with MIC 4-8 μg/mL comparable to standard drug ciprofloxacin, while the compounds, 4e and 4k showed maximum antifungal activity with MIC 8-16 μg/mL less active than standard drug fluconazole.
- Ahsan, Mohamed Jawed,Samy, Jeyabalan Govinda,Khalilullah, Habibullah,Nomani, Md. Shivli,Saraswat, Pankaj,Gaur, Ramakant,Singh, Abhimanyu
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p. 7246 - 7250
(2012/02/04)
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- Studies on fused heterocyclic 3,6-disubstituted-1,2, 4-triazolo-1,3,4- thiadiazoles: Synthesis and biological evaluation
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In this study, a series of 3,6-disubstituted-1,2, 4-triazolo-[3,4-b]-1,3,4- thiadiazoles (5a-t) were synthesized by condensing 4-amino-3-mercapto-(4H)-1,2, 4-triazoles (4a-c) with different aromatic or aroyl acids through one-pot reaction. The compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic, and lipid peroxidation actions. Some of the newly synthesized compounds showed very good anti-inflammatory activity with low GI toxicity and reduced lipid peroxidation. These compounds also showed interesting profile of analgesic activity in acetic acid-induced writhing test. The findings of the study indicate that the synthesized compounds have superior GI safety profile along with reduction in lipid peroxidation as compared to that of the standard. Springer Science+Business Media, LLC 2010.
- Husain, Asif,Naseer, Md. Arif
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scheme or table
p. 47 - 54
(2012/02/04)
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- N'-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene] 2/4-substituted hydrazides: Synthesis and anticonvulsant activity
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A series of N'-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene] 2/4-substituted hydrazides were synthesized using appropriate synthetic route and characterized by elemental analysis and spectral data. The anticonvulsant activity of some of the synthesized compounds were evaluated against maximal electroshock induced seizure (MES) and subcutaneous pentylenetetrazol (scPTZ) induced seizure models in mice. The neurotoxicity were assessed using the rotorod method. All the test compounds were administered at doses of 30, 100, and 300 mg/kg body weight and the anticonvulsant activity was noted at 0.5 and 4 h time intervals after the drug administration. Among the compound tested, all except 5g showed protection from seizures in both the animal models. Some titled compounds exhibited lesser CNS depression and neurotoxicity compared to phenytoin. A series of substituted hydrazide derivatives were synthesized, evaluated for their anticonvulsant potency in two animal models along with behavioural and neurotoxicity screen and also subjected to computational parameters.
- Kaushik, Darpan,Khan, Suroor Ahmad,Chawla, Gita,Kumar, Suresh
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experimental part
p. 3943 - 3949
(2010/09/11)
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- Design & synthesis of 2-(substituted aryloxy)-5-(substituted benzylidene)-3-phenyl-2,5-dihydro-1H-[1,2,4] triazin-6-one as potential anticonvulsant agents
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A series of 2-(substituted aryloxy)-5-(substituted benzylidene)-3-phenyl-2, 5-dihydro-1H-[1,2,4] triazin-6-one were designed & synthesized using appropriate synthetic route keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant activity and CNS activities. After intraperitoneal injection to mice, some synthesized derivatives were examined in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazol (scPTZ) induced seizure and neurotoxicity screens. Those found potent were also evaluated for behavioural impairment and depression activity. Among the compound tested, 5 eIX showed protection from seizures in both the animal models at dose level of 30 mg/kg while 5 bII & 5 cII showed protection against scPTZ model at same dose level. Some titled compounds exhibited lesser CNS depression and neurotoxicity compared to clinically effective drug. A series of substituted [1,2,4] triazin-6-one derivatives were synthesized, evaluated for their anticonvulsant potency on two animal models along with CNS activity and neurotoxicity and also subjected to computational parameter.
- Kaushik, Darpan,Khan, Suroor Ahmad,Chawla, Gita
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experimental part
p. 3960 - 3969
(2010/09/11)
-
- Synthesis and anticonvulsant activity of some novel fused heterocyclic l,2,4-triazolo-[3,4-b]-l,3,4-thiadiazole derivatives
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In the present investigation, a series of 3,6-disubstituted-l,2,4-triazolo- l,3,4-thiadiazole derivatives (6a-t) were synthesized and evaluated for their anticonvulsant activity and neurotoxicity. The structures of synthesized compounds were confirmed on the basis of their elemental analysis and spectral data results. In anti- MES activity compounds 6b, 6c, 6g, 6j, 6k, 6q and 6r showed potent activity comparable to that of standard drugs: phenytoin and carbamazepine. Compounds 6c, 6k, 6n, 6p and 6s successfully passed the rotorod test without any sign of neurological deficit.
- Husain, Asif,Naseer, Mohammad A.,Sarafroz, Mohammad
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scheme or table
p. 135 - 140
(2009/06/28)
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- Synthesis and structure of novel 1,2,4-triazole derivatives containing the 2,4-dinitrophenylthio group
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Some novel 1,2,4-triazole derivatives containing the 2,4-dinitrophenylthio group have been synthesised in high yields by means of the reactions of 3-substituted-4-amino -1H-1,2,4-triazole-5(4H)-thiones or (S-3-aryl-4- (benzylideneamino)-1H-l,2,4-triazole-5(4H)-thiones with 1-chloro-2,4- dinitrobenzene. The (S-3-aryl-4-(benzylideneamino)-1H-1,2,4-triazole-5(4H)- thiones were prepared by the reaction of 4-amino-3-aryl-2H-1,2,4-triazole-3(4H)- thiones and diverse aromatic aldehydes. The 2, 4-dinitrophenyl group linked to the S atom, not to the N atom, was confirmed by the crystal structures. The structures of all the compounds were determined by elemental analysis, IR, MS, 1H NMR and 13C NMR.
- Ding, Qichun,Lei, Xinxiang,Jin, Jianyu,Zhang, Lixue,Du, Huiai,Zhang, Haile
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scheme or table
p. 114 - 119
(2009/10/02)
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- Fenbufen based 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones as safer antiinflammatory and analgesic agents
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The synthesis of a series of 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones derived from 4-oxo-4-(biphenyl-4-yl)butanoic acid (fenbufen) is described. The structures of these compounds were supported by IR, 1H NMR, mass spectrometric data and elemental analysis. These compounds were tested for their antiinflammatory, analgesic, ulcerogenic and lipid peroxidation actions. A few compounds were found to have very good antiinflammatory activity in carrageenan induced rat paw edema test, while a fair number of compounds showed significant analgesic activity in acetic acid induced writhing test. The newly synthesized compounds showed very low ulcerogenic action with reduced malondialdehyde (MDA) content, which is one of the byproducts of lipid peroxidation. In vitro COX-1 and COX-2 isozyme inhibition studies were also performed on some of the selected compounds. Compound 4i and 4h were found to be more selective towards COX-2 as indicated by COX-2 selectivity index of 36.06 and 29.05 (COX-2 IC50 = 1.5 μM and 1.8 μM) respectively.
- Husain, Asif,Ahmad, Ausaf,Alam,Ajmal,Ahuja, Priyanka
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experimental part
p. 3798 - 3804
(2009/12/04)
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- 2-[3-(4-Chloro/ethyl phenyl)propan-3-one]-5-(substituted phenyl)-1,3,4-oxadiazoles: Synthesis and biological evaluation
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In the present investigation, two novel series of 2-[3-(4-chlorophenyl) propan-3-one]-5-(substituted phenyl)-1,3,4-oxadiazole and 2-[3-(4-ethylphenyl) propan-3-one]-5-(substituted phenyl)-1,3,4-oxadiazole were synthesized and tested for their antiinflammatory, analgesic, ulcerogenic and antibacterial actions. A fair number of compounds were found to have very good antiinflammatory activity in carrageenan induced rat paw edema test, while a few compounds showed significant analgesic activity in acetic acid induced writhing test. The newly synthesized compounds showed very low ulcerogenic action and moderate antibacterial action.
- Husain, Asif,Sarafroz, Mohammad,Ahuja, Priyanka
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scheme or table
p. 527 - 534
(2009/04/07)
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- Convenient synthesis of 4H-1,2,4-triazole-3-thiols using di-2-pyridylthionocarbonate
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We report here the convenient synthesis of 4H-1,2,4-triazole-3-thiols using di-2-pyridyl-thionocarbonate as the thiocarbonyl transfer reagent. This method is suitable for microplate parallel synthesis and produces samples in screening-ready condition. It
- Deprez-Poulain, Rebecca F.,Charton, Julie,Leroux, Virginie,Deprez, Benoit P.
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p. 8157 - 8162
(2008/03/13)
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- Synthesis and anti tuberculostatic activity of novel 1,3,4-oxadiazole derivatives
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A series of novel 2,5-disubstituted 1,3,4-oxadiazole derivatives were synthesized and tested for their in vitro antimycobacterial activity. Some compounds showed interesting activity against a strain of Mycobacterium tuberculosis H37Rv. The result of the antimycobacterial activity tests revealed that 2-(2-naphthyloxymethyl)-5-phenoxymethyl-1,3,4-oxadiazole (IVd) exhibited > 90% inhibition at MIC ~6.25.
- Shahar Yar,Ahmad Siddiqui,Ashraf Ali
-
-
- Oxadiazole mannich bases: Synthesis and antimycobacterial activity
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A series of oxadiazole mannich bases were synthesized by reacting oxadiazole derivatives, dapsone and appropriate aldehyde in the presence of methanol. The synthesized compounds were evaluated for antimycobacterial activity against M. tuberculosis H37Rv and INH resistant M. tuberculosis. Among the synthesized compounds, compound (4) 3-{2-furyl[4-(4-{2-furyl[5-(2-naphthyloxymethyl)-2-thioxo-2,3-dihydro-1,3,4-oxadiazol-3-yl]methylamino}phenylsulfonyl)anilino]methyl}-5-(2-naphthyloxymethyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione was found to be the most promising compound active against M. tuberculosis H37Rv and isoniazid (INH) resistant M. tuberculosis with Minimum inhibitory concentration (MIC) 0.1 μM & 1.10 μM respectively.
- Ali, Mohamed Ashraf,Shaharyar, Mohammad
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p. 3314 - 3316
(2008/02/08)
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- Synthesis and antiproliferative activity of 1-[(sub)]-6-fluoro-3-[(sub)]-1, 3,4-oxadiazol-2-yl-7-piperazino-1, 4-dihydro-4-quinolinone derivatives
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A series of 1-[(sub)]-6-fluoro-3- [(sub)]-1, 3, 4-oxadiazol-2-yl-7- piperazino-1, 4-dihydro 4-quinolinones were synthesized by the reaction between ciprofloxacin and norfloxacin with an appropriate acid hydrazide in phosphorous oxychloride. All newly synthesized compounds were evaluated for their antiproliferative activities against human lung tumor cell lines (A 549). Fluoroquinolone with oxadiazole (Q 2 ) 1-cyclopropyl-6-fluoro-3- [5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]-7-piperazino-1, 4-dihydro-4-quinolinone was found to be the most active compound in vitro with a half-maximal inhibitory concentration (IC50) of 9.0 μg/mL.
- Shaharyar, Mohammad,Ali, Mohamed Ashraf,Abdullah, Mohammad Mustaqeem
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p. 292 - 299
(2008/12/21)
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- An expedient method for the synthesis of acylhydrazones under microwave irradiation in solvent-free medium
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A simple, efficient and eco-friendly method for the synthesis of acylhydrazones from acylhydrazides and aldehydes under microwave (MW) irradiation was reported, no solvent and catalyst was used. The method is combined with a combinatorial approach and fou
- Li, Jian-Ping,Zheng, Peng-Zhi,Zhu, Jun-Ge,Liu, Rui-Jie,Qu, Gui-Rong
-
-
- Synthesis and evaluation of phenoxy acetic acid derivatives as anti-mycobacterial agents
-
In present investigation, 2-(4-formyl-2-methoxyphenoxy) acetic acid on condensation with various ketones in methanolic KOH solution yielded the corresponding chalcones (1-3). These corresponding chalcones were reacted with appropriate acid hydrazide in glacial acetic acid led to the formation of phenoxy acetic acid derivatives. All newly synthesized compounds were evaluated for their anti-mycobacterial activities against Mycobacterium tuberculosis H37Rv.
- yar, Mohammad Shahar,Siddiqui, Anees Ahmad,Ali, Mohamed Ashraf
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p. 4571 - 4574
(2007/10/03)
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- A rapid and high-yield synthesis of aryloxyacetyl hydrazides under microwave irradiation and with phase transfer catalysis
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A series of aryloxyacetyl hydrazides 4a-l were synthesised under microwave irradiation and phase transfer catalysis conditions. By the optimisation of the reaction conditions, a rapid, high-yield and efficient method for the preparation of aryloxyacety hydrazide was given.
- Wei, Tai-Bao,Liu, Hong,Li, Man-Lin,Zhang, You-Ming
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p. 432 - 433
(2007/10/03)
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- Synthesis of Aryloxyacetic Acids, Esters, and Hydrazides Assisted by Microwave Irradiation
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Under microwave irradiation on clay a series of transformations of a number of phenols into their aryloxyacetic acids 3 and then their methyl esters 4 and hydrazides 5 has been achieved efficiently in good yields.
- Hamid, Hamida M. Abdel,Ramadan, El Sayed,Hagar, Mohamed,El Ashry, El Sayed H.
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p. 377 - 382
(2007/10/03)
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- Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles
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Appropriate aryl-substituted unsymmetrical azodicarbonyl compounds, generated from bishydrazides by oxidation, undergo intramolecular cyclisations to furnish a variety of useful heterocycles such as N-substituted oxindoles, carbostyrils, benzazepinones, benzazocinones, benzimidazolones, benzoxazinones and pyrazolones in varying degrees of efficiency. Methods are described to remove the N-acyl groups from the heteroaromatic compounds. Under mildly acidic conditions where equal opportunities are available for an ipso or a normal cyclisation it is the former process that occurs preferentially. Evidence is presented in favour of a C-to-C migration in the ipso product for the formation of a methoxy-substituted carbostyril derivative. One of the spiro substances is shown to participate in dienone-phenol rearrangement to provide the corresponding quinolone-phenol in high yield.
- Prata, Jose V.,Clemente, Dina-Telma S.,Prabhakar, Sundaresan,Lobo, Ana M.,Mourato, Isabel,Branco, Paula S.
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p. 513 - 528
(2007/10/03)
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- Synthesis and in-vitro antimicrobial activity of new 1,2,4-triazoles
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We have described the synthesis of new 1,2,4-triazoles and have evaluated their antimicrobial profile. Antitubercular activity was determined in triplicate using the Lowenstein-Jensen medium. A loopful of Mycobacterium tuberculosis suspension was inoculated on the surface of each Lowenstein-Jensen media containing the test compounds (100, 10 or 1 μg mL-1). To evaluate in-vitro antibacterial activity, compounds (50, 5 or 0.5 μg) were evaluated against B. subtilis, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Staphylococcus typhi by the disc diffusion method. To evaluate antifungal activity Sabourauds Dextrose agar medium was used. Some of the compounds (5, 0.5 or 0.05 μg mL-1) were screened for activity against Aspergillus niger 88 and Aspergillus niger 90 and others were screened for activity against T. rubrum TR1, T. rubrum R6, T. rubrum R7 and T. mentagrophyte M1, using the cup plate method. Our results show that the triazoles with a pyrazine moiety at position 3 were more active as antitubercular and antifungal agents compared with the triazoles which had a pyrazine moiety at position 4 of the molecule.
- Bhat,Bhat,Shenoy
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p. 267 - 272
(2007/10/03)
-