Synthesis and antimicrobial and pharmacological properties of new thiosemicarbazide and 1,2,4-triazole derivatives

✍ Scribed by Łukasz Popiołek; Maria Dobosz; Anna Chodkowska; Ewa Jagiełło-Wójtowicz; Urszula Kosikowska; Anna Malm; Liliana Mazur; Zofia Rzączyńska

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2010
• Tongue: English
• Weight: 235 KB
• Volume: 48
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.563

✦ Synopsis

Abstract

Reaction of 4‐phenyl‐4__H__‐1,2,4‐triazole‐3‐thione with ethyl bromoacetate has led to the formation of ethyl [(4‐phenyl‐4__H__‐1,2,4‐triazol‐3‐yl)sulfanyl]acetate 1, the structure of which was confirmed by X‐ray analysis. In the next reaction with 80% hydrazide hydrate, appropriate hydrazide 2 was obtained, which in reaction with isothiocyanates was converted to new acyl derivatives of thiosemicarbazides 2, 3, 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h. The cyclization of these compounds in alkaline media has led to formation of new derivatives of 5‐{[(4‐phenyl‐4__H__‐1,2,4‐triazole‐3‐yl)sulfanyl]methyl}‐4__H__‐1,2,4‐triazole‐3(2__H__)‐thiones 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4j. The structure of the compounds was confirmed by elementary analysis and IR, ^1^H‐NMR, ^13^C‐NMR, and MS spectra. Compounds 2, 3, 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h and 4a, 4b, 4c, 4d, 4e, 4f, 4g were screened for their antimicrobial activities, and the influence of the compounds 4a, 4b, and 4e, 4f, 4g on the central nervous system of mice in behavioral tests was examined. J. Heterocyclic Chem., (2011).