Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity

Bektas H., DEMİRBAŞ A., DEMİRBAŞ N., Karaoglu S. A.

TURKISH JOURNAL OF CHEMISTRY, vol.34, no.2, pp.165-180, 2010 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 2
  • Publication Date: 2010
  • Doi Number: 10.3906/kim-0905-36
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.165-180
  • Karadeniz Technical University Affiliated: Yes

Abstract

2-{3-(4-Substitutedbenzyl)-4-[2-(1H-indol-3-yl) ethyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N'-(arylmethylene) acetohydrazides (5a-g), 4-amino-2-{3-(4-substitutedbenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N'-(arylmethylene) acetohydrazides (6a,b), and 4-[2-(1H-indol-3-yl) ethyl]-5-(4-substitutedbenzyl)-2-{[5-(phenylamino)-1,3,4-thiadiazol-2-yl] methyl}-2,4-dihydro-3H-1,2,4-triazol-3-ones (8a,b) were synthesized starting from 4-alkyl-5-(4-substitutedbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-ones (2a-c) by several steps and their structures were well characterized by elemental analyses, IR, (1)H-NMR, (13)C-NMR, and mass spectral studies. They were also screened for their microbial activities. The obtained antimicrobial activity results revealed that 12 among the 24 compounds tested displayed variable growth inhibition effects on the tested gram-positive and gram-negative bacterial strains. None of the compounds showed antifungal activity against yeast-like fungi.

2-{3-(4-Substitutedbenzyl)-4-[2-(1H-indol-3-yl) ethyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N'-(arylmethylene) acetohydrazides (5a-g), 4-amino-2-{3-(4-substitutedbenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N'-(arylmethylene) acetohydrazides (6a,b), and 4-[2-(1H-indol-3-yl) ethyl]-5-(4-substitutedbenzyl)-2-{[5-(phenylamino)-1,3,4-thiadiazol-2-yl] methyl}-2,4-dihydro-3H-1,2,4-triazol-3-ones (8a,b) were synthesized starting from 4-alkyl-5-(4-substitutedbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-ones (2a-c) by several steps and their structures were well characterized by elemental analyses, IR, H-1-NMR, C-13-NMR, and mass spectral studies. They were also screened for their microbial activities. The obtained antimicrobial activity results revealed that 12 among the 24 compounds tested displayed variable growth inhibition effects on the tested gram-positive and gram-negative bacterial strains. None of the compounds showed antifungal activity against yeast-like fungi.