Cyclization of some carbothioamide derivatives containing antipyrine and triazole moieties and investigation of their antimicrobial activities

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

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, cilt.45, sa.11, ss.4726-4732, 2010 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 45 Sayı: 11
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1016/j.ejmech.2010.07.018
  • Dergi Adı: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4726-4732
  • Anahtar Kelimeler: 1H-pyrazole, 1,3,4-Oxadiazole, 1,2,4-Triazole, 1,3,4-Thiadiazole, 1,3-Thiazole, Antimicrobial activity, ANALGESIC ACTIVITY, HYBRID MOLECULES, AKT INHIBITORS, AGENTS, DESIGN, THIAZOLIDINONES, ANTIBACTERIAL, RING
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

Acetohydrazide derivative containing both antipyrine and triazole nuclei (5) was obtained starting from ethyl hydrazinecarboxylate derivative (2) and 4-aminoantipyrine (1) by three steps. The treatment of compound 5 with CS2 afforded the conversion of hydrazide function into 5-mercapto-1,3,4-oxadiazole ring leading to the formation of 7. Then, 7 gave the product containing triazolotriazine moiety (9) by the reaction with hydrazine hydrate. The synthesis of the compounds incorporating the 1,3,4-thiadiazole (10a-c), 1,2,4-triazole (11a-c) or 1,3-thiazole (12, 13) nucleus as third heterocycle was performed by the acidic or basic treatment of compounds 6a-c which were obtained from the reaction of 5 with several isothiocyanates, or by the condensation of 6a with two different phenacyl bromides, respectively.