Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities


BAYRAK H., DEMİRBAŞ A., Karaoglu Ş., DEMİRBAŞ N.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, cilt.44, sa.3, ss.1057-1066, 2009 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 44 Sayı: 3
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1016/j.ejmech.2008.06.019
  • Dergi Adı: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1057-1066
  • Anahtar Kelimeler: Isonicotinic acid hydrazide, 1,2,4-Triazole, 1,3,4-Oxadiazole, 1,3,4-Thiadiazole, Antimicrobial activity, ANTIBACTERIAL ACTIVITY, DERIVATIVES, ANTICANCER, AGENTS, ACID
  • Recep Tayyip Erdoğan Üniversitesi Adresli: Evet

Özet

4-Phenyl-5-pyridin-4-yl-4H-1,2,4-triazole-3-thiol (3) was obtained in basic media via the formation of 2-isonicotinoyl-N-phenylhydrazine-carbothioamide (2), and converted to some alkylated derivatives (4a,b) and Mannich base derivatives (5a-c). 2-[(4-Phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]acetohydrazide (7) that was obtained by using compound 3 as precursor in two steps was converted to thiosemicarbazide derivative (8), Schiff base derivatives (9) and 5-([(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]methyl)-1,3,4-oxadiazole-2-thiol (10). Moreover, 5-([(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]methyl)-3-{[(2-morpholin-4-ylethyl)amino]methyl}-1,3,4-oxadiazole-2(3H)-thione (11) was synthesized via reaction of compound 10 with 2-(4-morpholino)ethylamine. The treatment of compound 8 with NaOH gave 4-(4-methylphenyl)-5-{[(4-phenyl-5-pyridine-4-yl-4H-1,2,4-triazol-3-yl)thio]methyl}-4H-1,2,4-triayole-3-thiol (12), while the acidic treatment of compound 8 afforded 5-{[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]methyl}-2(4-methylphenyl)-amino-1,3,4-thiadiazole (14). N-Methyl derivative of compound 14 and a Mannich base derivative of compound 12 were synthesized from the reactions of these precursors with methyl iodide and methyl piperazine, respectively.