Synthesis and evaluation of 4-amino-5-phenyl-4H-[1,2,4]-triazole-3-thiol derivatives as antimicrobial agents

Sahoo, Prasanta Kumar; Sharma, Rajesh; Pattanayak, Priyabrata

doi:10.1007/s00044-009-9178-8

Cited by 55 publications

(24 citation statements)

References 17 publications

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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%

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Synthesis and Structure-Activity Relationship of N-(3-Oxo-1-Thia-4-Azaspiro[4.5]Decan-4-Yl)Carboxamide Inhibitors of Influenza Virus Hemagglutinin Mediated Fusion

Göktaş

Vanderlinden

Naesens

et al. 2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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We report on synthesis and the structure-activity relationship of carboxamide-derived inhibitors of the influenza virus fusion function of the viral hemagglutinin. The newly synthesized carboxamides have a backbone structure similar to reported fusion inhibitors, consisting of an aromatic ring system linked to a non-aromatic cyclic system via an amide bridge. Condensation of 2-hydroxybenzohydrazide, 5-chloro-2-hydroxybenzohydrazide or 3-hydroxynaphthalene-2-carbohydrazide, appropriate carbonyl compounds and sulfanyl acids yielded corresponding N-(3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl)carboxamides, using a one-pot three-component cyclocondensation method. The compounds were characterized by IR, 1 H-NMR, 13 C-NMR and elemental analysis. All compounds were evaluated for antiviral activity against influenza A (H1N1, H3N2) and influenza B viruses in MDCK cell cultures. The contributions of different substituents on the antiinfluenza effect were discussed.

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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%

Synthesis and Structure-Activity Relationship of N-(3-Oxo-1-Thia-4-Azaspiro[4.5]Decan-4-Yl)Carboxamide Inhibitors of Influenza Virus Hemagglutinin Mediated Fusion

Göktaş

Vanderlinden

Naesens

et al. 2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…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%

Chloroacetylenephosphonates in reactions with tetrazolethiones

2014

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Chloroacetylenephosphonates react with 1 substituted tetrazole 5 thiones in anhydrous acetonitrile to form fused heterocycles, viz., 3 substituted 6 (dialkoxyphosphoryl) 3H thiazolo [3,2 d]tetrazol 7 ium chlorides, along with a small amount of compounds having a linear structure, viz., Z dialkyl {1,2 bis[(1 methyl(phenyl) 1H tetrazol 5 yl)sulfanyl]ethenyl} phosphonates.Chloroacetylenephosphonates were synthesized for the first time in 1965. 1 These compounds came to the atten tion of chemists due to the presence of several highly reac tive centers in their structure: an acetylenic bond, a labile halogen atom, and an electron withdrawing phosphonate group. Various possible applications of these compounds for the synthesis of phosphorus containing carbo and het erocycles, addition products at the triple bond, and vari ous compounds with retention of the triple bond were described in the literature. 2,3In the present study, we consider a new area of the use of chloroacetylenephosphonates in the synthesis of phos phorylated fused heterocycles. Five membered heterocy cles with two or three heteroatoms, such as imidazoles, thiazoles, triazoles, and so on, serve as key structural blocks for many pharmacological agents. 4-8 The conventional method for the synthesis of these compounds is based on reactions of binucleophiles (diamines, diols, thioleamines containing nucleophilic groups at adjacent carbon atoms) with carbonyl compounds and carboxylates. In the past decades, acetylenes and haloacetylenes have found increas ing use for the design of heterocyclic structures. The reac tivity of haloacetylenes increases in the presence of an electron withdrawing activating group, such as a carbon yl, carboxyl, or phosphoryl group, at the triple bond. One of advantages of the use of haloacetylenes for the heterocyclization is that their reactions, as opposed to reactions with carbonyl (carboxyl) reagents, do not pro duce a water molecule, which can have an effect on the course of the reaction.The reactions of haloacetylenephosphonates with bi nucleophiles usually proceed with high regioselectivity via the attack of both nucleophilic centers on the haloacetyl ene carbon atom. Thus, the reactions of chloroacetylene phosphonates with o phenylenediamine, o aminophenol, 1,2 alkanediols, and 1,2 ethanolamines afford (dialk oxyphosphorylmethyl)benzimidazoles, benzoxazoles, 1,3 oxolanes, and 4,5 dihydrooxazoles, respectively. 3 This reaction of 2 acyl 1 bromoacetylenes with 4 ami no 5 phenyl 3 thio 1,2,4 triazole proceeds through the same pathway. 9 In this study, it was shown that the reac tion produces fused aromatic systems due to the involve ment of two nucleophilic centers (sulfur and the NH 2 group of thiotriazole) and one electrophilic center (the haloacetylene carbon atom). 2 Acylmethylene 5 phenyl 3H 1,3,4 thiadiazolo[2,3 c] 1H(2H) 1,2,4 triazolium bromides were synthesized in 65-69% yields (Scheme 1). Scheme 1 R = Ph, 2 thienylIn a continuation of our studies of the reactivity and synthetic potential of chloroacetylenephosphona...

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“…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%

Complexation of manganese(II), cobalt(II), nickel(II) and copper(II) by a ligand derived from 1,2,4-triazole: Potentiometric studies and Density Functional Theory calculations

et al. 2013

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KEYWORDSDFT calculations have been conducted to understand the conformational and tautomeric preference of 4-amino-5-(2-hydroyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione ligand. The results suggest that the thione tautomer is found to be the most stable form in the gas phase, which is in very good agreement with the FT-IR and crystallographic data. The protonation constants of the ligand and the stability constants of its complexes with Mn(II), Co(II), Ni(II) and Cu(II) have been determined by potentiometry in water-ethanol (90:10, v:v) mixture. The absolute pKa values of the ligand have been calculated using DFT method to complement and help the assignment of potentiometric data. DFT calculations have also been carried out for some metallic complexes species formed in solution in order to propose their most probable structures.Potentiometry DFT calculations Stability constants 1,2,4-Triazole ligand Dissociation constants Thione-thiol tautomerism

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Synthesis and evaluation of 4-amino-5-phenyl-4H-[1,2,4]-triazole-3-thiol derivatives as antimicrobial agents

Cited by 55 publications

References 17 publications

Synthesis and Structure-Activity Relationship of N-(3-Oxo-1-Thia-4-Azaspiro[4.5]Decan-4-Yl)Carboxamide Inhibitors of Influenza Virus Hemagglutinin Mediated Fusion

Synthesis and Structure-Activity Relationship of N-(3-Oxo-1-Thia-4-Azaspiro[4.5]Decan-4-Yl)Carboxamide Inhibitors of Influenza Virus Hemagglutinin Mediated Fusion

Chloroacetylenephosphonates in reactions with tetrazolethiones

Complexation of manganese(II), cobalt(II), nickel(II) and copper(II) by a ligand derived from 1,2,4-triazole: Potentiometric studies and Density Functional Theory calculations

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