Synthesis and antimicrobial and antitumor activitiy of some new (1,2,4) triazole-5-one derivatives

ÜNVER Y., DÜĞDÜ E., SANCAK K., ER M., Alpay Karaoğlu Ş.

Turkish Journal of Chemistry, cilt.33, sa.1, ss.135-147, 2009 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 33 Sayı: 1
  • Basım Tarihi: 2009
  • Dergi Adı: Turkish Journal of Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.135-147
  • Recep Tayyip Erdoğan Üniversitesi Adresli: Evet

Özet

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 3ag 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, $^1 H-NMR$, $^{13}C-NMR$, and elemental analyses. Compounds 2, 3a, 3c, 3g, 4f, 5b, and 5g showed good antifungal activity against yeast-like fungi. Compounds selected by the National Cancer Institute (NCI, USA) were investigated for antitumor activity.