ChemInform Abstract: Synthesis of Oxadiazolyl‐, Thiadiazolyl‐ and Triazolylindoles and Indolylthiazolidinones.

Hiremath, S. P.; Sonar, Vijayakumar N.; Sekhar, K. R.; Purohit, M. G.

doi:10.1002/chin.198949148

Cited by 3 publications

(4 citation statements)

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“…Several methods have been used for the synthesis of these kinds of compounds from acylic precursors. Some of them are the oxidative cyclizations of acyl hydrazones, acyl thioureas, and acyl thiosemicarbazides …”

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“…1 Several methods have been used for the synthesis of these kinds of compounds from acylic precursors. Some of them are the oxidative cyclizations of acyl hydrazones, 2 acyl thioureas, 3 and acyl thiosemicarbazides. 4 The present work deals with the oxidation of a copper(II) 3,4-oxadiazole) in which the ligand has undergone a series of reactions which have been summarized in Scheme 1.…”

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Evidence of Desulfurization in the Oxidative Cyclization of Thiosemicarbazones. Conversion to 1,3,4-Oxadiazole Derivatives

et al. 2002

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The addition of pyridine-2-carbaldehyde 4N-methylthiosemicarbazone (C8H10N4S) to an aqueous solution of copper(II) nitrate yields [[Cu(C8H9N4S)(NO3)]2] (1). This complex consists of centrosymmetric dinuclear entities containing square-pyramidal copper(II) ions bridged through the sulfur thioamide atoms. The oxidation of 1 with KBrO3 or KIO3 gives rise to a compound with formula [[Cu(C8H8N4O)(H2O)2(SO4)]2]*2H2O (2) (C8H8N4O = 2-methylamino-5-pyridin-2-yl-1,3,4-oxadiazole). The structure of 2 is made up of centrosymmetric dimers where the copper(II) ions exhibit a distorted octahedral coordination and are connected by the oxadiazole moiety. The metal ions in 2 can be removed by addition of K4[Fe(CN)6], and then the oxadiazole ligand can be isolated and recrystallized as (C8H8N4O)*3H2O (3).

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Evidence of Desulfurization in the Oxidative Cyclization of Thiosemicarbazones. Conversion to 1,3,4-Oxadiazole Derivatives

et al. 2002

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“…Triazole is well known for its antimicrobial property and widely used to treat microorganisms associated diseases [11]. Besides, the antibacterial [12][13][14][15] and antifungal [16][17][18][19] activity; 1,2,4-triazole possess, anti-inflammatory [20], as well as antioxidants properties [21]. Various well-known drug commercialized in the market possesses 1,2,4-triazole moiety such as Fluc, terconazole,…”

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Antimicrobial Investigation and Binding Mode Analysis of Some Newly Synthesized 4-Amino-5-((Aryl Substituted)-4h-1, 2, 4-Triazole-3-Yl)-Thio Linked Hydroxamic Acid Derivatives

Das

et al. 2019

Asian J Pharm Clin Res

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Objective: A series of 5-substituted-4-amino-1, 2, 4-triazole-linked hydroxamic acid derivatives have been synthesized and explored in vitro to evaluate antibacterial and antifungal activities. Methods: Different 5-phenyl group substituted-4-amino-1,2,4-triazole-3-thiol reacted with chlorine substituted hydroxamic acid to produce the desired compounds and characterized spectroscopically. Minimum inhibitory concentration (MIC), zone of inhibition (ZOI), growth kinetic studies, and scanning electron microscopy (SEM) were employed to elicit the antimicrobial efficacy of synthesized compounds against a wide range of bacterial and fungal strains. Results: Compounds 6a, 6b, 6d, and 6k (MIC of 25 μg/ml) have been found to be more potent against Klebsiella pneumoniae, Bacillus cereus, Bacillus pumilus, Micrococcus luteus, and Pseudomonas aeruginosa, compounds 6a-6d, 6k, and 6l (MIC of 25–50 μg/ml) have shown potent antibacterial efficacy against Klebsiella pneumonia, P. aeruginosa, and Vibrio cholera compare to the standard drug amoxicillin (MIC of 60 μg/ml, 65 μg/ml, and 25 μg/ml, respectively). Screening for the antifungal activity revealed that the compounds were found to be most active against Candida albicans (6a, 6b, and 6l), Candida tropicalis (6b and 6d), and Aspergillus niger (6a, 6b, 6d, and 6j) with MIC of 15–25 μg/ml. Bacteriostatic and fungistatic effect of titled compounds was revealed from growth kinetics study. Conclusion: Electron donating group at the 5-position of the 5-substituted-1,2,4-triazole-linked hydroxamic acid derivatives conferred the biological effectiveness of the synthesized compounds and also offer a therapeutically effective prototypical structure for further development of new chemical entities with superior antimicrobial activity.

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“…Introduction 5-Substituted-1,2,4,-triazole-3-thiones have been shown to posses diverse biological activities including antibacterial [1,2], antifungal [3,4], antithyroid [5], hypoglycaemic [6], and antidepressant [7,8]. Previous reports have also dealt extensively with the tautomerism encountered in such structures [9].…”

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Experimental and theoretical structural studies on 4-(2-phenylethyl)-5-(2-furyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

Karayel

Özbey

2008

Struct Chem

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The structural and conformational features of 4-(2-phenylethyl)-5-(2-furyl)-2, 4-dihydro-3H-1,2,4-triazole-3-thione (1a), which can be related to the biological activity, have been investigated by X-ray diffraction and molecular modeling techniques. Ab initio method (RHF/6-31G) and density functional theory (B3LYP/6-31G(D)) have been used to calculate structural parameters, conformations, and relative energy of two tautomeric specious (1a and 1b) of the title compound. The geometry and the conformation of the thione form, 1a, is well reproduced by the DFT (B3LYP/6-31G(D)) method as compared with X-ray structure in which this form is found. The thione form is also predicted to be 14.42 kcal/mol more stable than the thiol form in the gas-phase by the DFT method.

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ChemInform Abstract: Synthesis of Oxadiazolyl‐, Thiadiazolyl‐ and Triazolylindoles and Indolylthiazolidinones.

Abstract: Fourteen compounds of type (III) are prepared and transformed to the heterocyclic systems (IV)‐(VI).

Cited by 3 publications

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Evidence of Desulfurization in the Oxidative Cyclization of Thiosemicarbazones. Conversion to 1,3,4-Oxadiazole Derivatives

Evidence of Desulfurization in the Oxidative Cyclization of Thiosemicarbazones. Conversion to 1,3,4-Oxadiazole Derivatives

Antimicrobial Investigation and Binding Mode Analysis of Some Newly Synthesized 4-Amino-5-((Aryl Substituted)-4h-1, 2, 4-Triazole-3-Yl)-Thio Linked Hydroxamic Acid Derivatives

Experimental and theoretical structural studies on 4-(2-phenylethyl)-5-(2-furyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

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