2009
DOI: 10.1007/s00044-009-9178-8
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Synthesis and evaluation of 4-amino-5-phenyl-4H-[1,2,4]-triazole-3-thiol derivatives as antimicrobial agents

Abstract: A series of novel 1,2,4-triazole derivatives have been synthesized by condensing the methyl benzoate and methyl salicylate with various substituents; their structures were established on the basis of elemental analysis, Fourier transform infrared spectroscopy (FTIR), 1 H nuclear magnetic resonance (NMR), and mass spectral data. All title compounds were subjected to in vitro antibacterial and antifungal screening against four different bacterial and fungal strains. Preliminary results indicate that some of them… Show more

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Cited by 55 publications
(24 citation statements)
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“…The ring closure is believed to proceed via an imine formation in the first step, followed by attack of sulfur nucleophile on the imine carbon and, finally, intramolecular cyclization with the elimination of water. 15,16 The synthetic method (one-pot three components) employed for the preparation of the compounds in this study is outlined in Figure 2. Refluxing a mixture of hydrazides and the appropriate cyclic ketone together with sulfanylacetic acid or 2-sulfanylpropanoic acid in dry benzene using a Dean-Stark aparatus afforded the target compounds 3a-3g, 4a-4f, 5a-5f, 6a-6e, 7a-7d.…”
Section: Chemistrymentioning
confidence: 99%
See 1 more Smart Citation
“…The ring closure is believed to proceed via an imine formation in the first step, followed by attack of sulfur nucleophile on the imine carbon and, finally, intramolecular cyclization with the elimination of water. 15,16 The synthetic method (one-pot three components) employed for the preparation of the compounds in this study is outlined in Figure 2. Refluxing a mixture of hydrazides and the appropriate cyclic ketone together with sulfanylacetic acid or 2-sulfanylpropanoic acid in dry benzene using a Dean-Stark aparatus afforded the target compounds 3a-3g, 4a-4f, 5a-5f, 6a-6e, 7a-7d.…”
Section: Chemistrymentioning
confidence: 99%
“…Hydroxybenzohydrazide and 5-chloro-2-hydroxybenzohydrazide were prepared according to the previously reported methods 16,17. Melting points (mp) were determined on a Büchi 530 capillary melting point apparatus in open capillaries and were uncorrected.…”
mentioning
confidence: 99%
“…We found 10,11 that, unlike the reactions described in the literature, 9 the reaction of chloroacetylenephospho nates with 4,5 substituted 1,2,4 triazole 3 thiones, the thione structure of which was established by 15 N NMR spectroscopy, proceeds with high chemo and regioselec tivity to form new heterocyclic compounds, viz., 2,3 sub stituted 6 (dialkoxyphosphoryl) 3H thiazolo [3,2 b] [1,2,4] triazol 7 ium chlorides (Scheme 2). This reaction pathway was observed also for 1 substi tuted tetrazole 5 thiones.…”
Section: R = Ph 2 Thienylmentioning
confidence: 99%
“…The substituted 1,2,4-triazoles attracted more attention than the unsubstituted one, because they also display a broad range of biological activity, finding application as antitumor, antibacterial, antifungal and antiviral agents and exhibit rich coordination modes, leading to new complexes with innovative structures [1][2][3][4][5][6][7].…”
Section: Introductionmentioning
confidence: 99%