Synthesis and Antimicrobial and Antitumor Activity of Some New [1,2,4] Triazole-5-one Derivatives

Uenver Y., Duegdue E., SANCAK K., Er M., Karaoglu Ş.

TURKISH JOURNAL OF CHEMISTRY, vol.33, no.1, pp.135-147, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 33 Issue: 1
  • Publication Date: 2009
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.135-147
  • Keywords: Triazole-5-one, acetophenone, NaBH4, antimicrobial and antitumor activity, AROMATASE INHIBITORS, ANTIBACTERIAL, AGENTS
  • Recep Tayyip Erdoğan University Affiliated: Yes


4-[Arylidene-amino]-3-thiophen-2-ylmethyl-4,5-dihydro[1,2,4]triazole-5-one compounds (3a-g) with Schiff base character were obtained from the reaction of 4-amino-3-thiophen-2-ylmethyl-4,5-dihydro-1H-[1,2,4]triazole-5-one (2) with various aldehydes. 1-(2-Oxo-2-phenyl-ethyl)-4-[arylidene-amino]-3-thiophen-2-ylmethyl-4,5-dihydro-1H-[1,2,4]triazole-5-ones (4a-g) were synthesized from the reaction of corresponding compounds 3a-g with bromoacetophenone. 1-(2-Hydroxy-2-phenyl-ethyl)-3-thiophen-2-ylmethyl-4-[aryl-amino]4,5-dihydro-1H-[1,2,4]triazole-5-ones (5a-g) and 1-(2-hydroxy- 2-phenyl-ethyl)-3-thiophen-2-ylmethyl-4-[arylidene-amino]4,5-dihydro-1H-[1,2,4]triazole-5-ones (6b,d,e) were obtained from the selective reduction of 1-(2-oxo-2-phenylethyl)-4-[arylidene-amino]-3-thiophen-2ylmethyl-4,5-dihydro-1H-[1,2,4]triazole-5-ones (4) with NaBH4. They were characterized by IR, H-1-NMR, C-13-NMR, and elemental analyses. Compounds 2, 3a, 3c, 3g, 4f, 5b, and 5g showed good antifungal activity against yeast-like fungi.