Cyclization of some carbothioamide derivatives containing antipyrine and triazole moieties and investigation of their antimicrobial activities
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, cilt.45, sa.11, ss.4726-4732, 2010 (SCI-Expanded, Scopus)
- 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.