Synthesis of heterocycles. Part VI. Synthesis and antimicrobial activity of some 4‐amino‐5‐aryl‐1,2,4‐triazole‐3‐thiones and their derivatives

Abstract

4‐Amino‐5‐aryi‐1,2,4‐triazole‐3‐thiones I react with acid chlorides to yield 4‐acylamino‐5‐aryl‐1,2,4‐triazole‐3‐thiones II. Compounds I also react with methylene iodide, chloroacetonitrile and methyl bromoacetate to give bis‐(4‐amino‐5‐aryl‐1,2,4‐triazol‐3‐ylthio)methanes III, 4‐amino‐5‐aryl‐3‐cyanomethylthio‐1,2,4‐triazoles IV and 4‐amino‐5‐aryl‐3‐carbomethoxymethylthio‐1,2,4‐triazoles V, respectively. Compounds V react with hydrazine hydrate to give the corresponding acid hydrazides VI which in turn condenses with acid chlorides and aldehydes to afford respectively 1‐[(4‐amino‐5‐aryl‐1,2,4‐triazol‐3‐ylthio)acetyl]‐2‐aroylhydrazines VII and aryl methylene (4‐amino‐5‐aryl‐1,2,4‐triazol‐3‐ylthio)acethydrazones VIII. The antimicrobial activities of the above compounds were screened against different strains of bacteria and fungi.

Synthesis of spiro-1,2,4-triazole-3-thiones from cycloalkanone thiosemicarbazones, and formation of a cyclic 1,2-dithione

“…A series of spiro-cycloalkylidene [1,2,4]triazole-3-thione derivatives was synthesized via oxidative cyclization of cyclic-ylidene-N-substituted hydrazinecarbothioamides by using benzoand naphthoquinone derivatives. The simple reactivity of cycloalkylidene-N-substituted hydrazinecarbothioamides required the availability of cyclic-C=N and the nucleophilic sites thioamide-NH , s. It was found that solvent, temperature and the molar ratio of reactants may all play a critical role in the reaction efficiency.…”

“…1 Also, heterocyclic 1,2,4-triazoline-5-thione derivatives exhibited various biological properties such as analgesic, 2 anti-inflammatory, 3 bacteriostatic 4 and antimitotic 5 activities.…”

4-Benzyl-1,2,4-triazaspiro[4.5]dec-1-ene-3-thione

“…Heterocyclic 1,2,4-triazoline-5-thione derivatives exhibit a variety of biological properties including analgesic (Mekuskiene et al, 1998), anti-inflammatory (Sahin et al, 2001), bacteriostatic (Eweiss et al, 1986) and antimitotic (Wujec et al, 2004) activities. As part of our studies in this area, we determined the crystal structure of the title triazathione compound (Fig.…”

Potentiometric Determination of Pharmaceutically Important Nimesulide in Non-Aqueous Medium

“…Some of the present day drugs such as ribavirin (antiviral agent), rizatriptan (antimigraine agent), alprazolam (anxiolytic agent), fluconazole and itraconazole (antifungal agents) are the best examples for potent molecules possessing triazole nucleus [5][6][7] . Many literatures have shown that Mannich bases possess potent biological activities such as antibacterial, antifungal, anti-inflammatory, antimalarial and pesticide properties [8][9][10][11] . Few Mannich bases derived from 1,2,4-triazoles carrying N-methylpiperzine substituent were biologically active 12,13 .…”