title: Cyclization of some carbothioamide derivatives containing antipyrine and triazole moieties and investigation of their antimicrobial activities.
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 CS(2) 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. The antimicrobial activity study revealed that all the compounds showed good activities except 3-5.
authors: Karadeniz Technical University, Department of Chemistry 61080 Trabzon, Turkey.
authors: Hacer
authors: H
authors: Bayrak
authors: Ahmet
authors: A
authors: Demirbas
authors: Neslihan
authors: N
authors: Demirbas
authors: Sengül Alpay
authors: SA
authors: Karaoglu
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology*; D000983:Antipyrine / Q000737:chemistry*; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000890:Anti-Infective Agents; D014230:Triazoles; D000983:Antipyrine