4.3 Article

Design, Synthesis, Characterization and Antimicrobial Evaluation of Some Heterocyclic Condensed Systems with Bridgehead Nitrogen from Thiazolotriazole Class

期刊

CHEMICAL & PHARMACEUTICAL BULLETIN
卷 63, 期 9, 页码 694-700

出版社

PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c15-00379

关键词

thiazolo[3,2-b][1,2,4]triazole; 1,2,4-triazole-3-thiole; alkylation; antimicrobial activity

资金

  1. Sectoral Operational Programme Human Resources Development - European Social Fund
  2. Romanian Government [POSDRU/89/1.5/S/64109]

向作者/读者索取更多资源

In the present study, a series of new heterocyclic condensed systems with bridgehead nitrogen from the thiazolo[3,2-b][1,2,4]triazoles class was synthesized starting from some 4-(4-X-phenylsulfonyl)phenyl)-4H-1,2,4-triazole-3-thioles 1a-c (X=H, Cl, Br). The intermediates of S-alkylated 1,2,4-triazoles, 2-(5-(4-(4-X-phenylsulfonyl)phenyl)-2H-1,2,4-triazol-3-ylthio)-1-(4-fluorophenyl)ethanones 2a-c, were obtained by treatment of triazoles 1a-c with 2-bromo-4'-fluoroacetophenone. The 2-(4-(4-X-phenylsulfonyl)phenyl)-6-(4-fluorophenyl)thiazolo[3,2-b][1,2,4]triazoles 3a-c were obtained by cyclization of S-alkylated 1,2,4-triazoles 2a-c in sulfuric acid media, at 0 degrees C. For the synthesis of 2-(4-(4-X-phenylsulfonyl)phenyl)-5-(4-fluorobenzylidene)thiazolo[3,2-b][1,2,4]triazol-6(5H)-ones 4a-c, the triazoles 1a-c were treated with 4-fluorobenzaldehyde, chloroacetic acid and anhydrous sodium acetate, in the presence of acetic acid and acetic anhydride. The structures of the newly synthesized compounds have been confirmed by elemental analysis and spectral methods (IR, H-1-NMR, C-13-NMR, MS). The antimicrobial activity of all new compounds has been screened against some bacteria and yeasts.

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