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, vol.45, no.11, pp.4726-4732, 2010 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 45 Issue: 11
  • Publication Date: 2010
  • Doi Number: 10.1016/j.ejmech.2010.07.018
  • Journal Name: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4726-4732
  • Keywords: 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
  • Recep Tayyip Erdoğan University Affiliated: Yes

Abstract

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.