Barbuceanu Stefania-Felicia, Draghici Constantin, Barbuceanu Florica, Bancescu Gabriela, Saramet Gabriel
Organic Chemistry Department, Faculty of Pharmacy, "Carol Davila" University of Medicine and Pharmacy.
Chem Pharm Bull (Tokyo). 2015;63(9):694-700. doi: 10.1248/cpb.c15-00379.
In the present study, a series of new heterocyclic condensed systems with bridgehead nitrogen from the thiazolo[3,2-b][1,2,4]triazoles class was synthesized starting from some 4-(4-X-phenylsulfonyl)phenyl)-4H-1,2,4-triazole-3-thioles 1a-c (X=H, Cl, Br). The intermediates of S-alkylated 1,2,4-triazoles, 2-(5-(4-(4-X-phenylsulfonyl)phenyl)-2H-1,2,4-triazol-3-ylthio)-1-(4-fluorophenyl)ethanones 2a-c, were obtained by treatment of triazoles 1a-c with 2-bromo-4'-fluoroacetophenone. The 2-(4-(4-X-phenylsulfonyl)phenyl)-6-(4-fluorophenyl)thiazolo[3,2-b][1,2,4]triazoles 3a-c were obtained by cyclization of S-alkylated 1,2,4-triazoles 2a-c in sulfuric acid media, at 0 °C. For the synthesis of 2-(4-(4-X-phenylsulfonyl)phenyl)-5-(4-fluorobenzylidene)-thiazolo[3,2-b][1,2,4]triazol-6(5H)-ones 4a-c, the triazoles 1a-c were treated with 4-fluorobenzaldehyde, chloroacetic acid and anhydrous sodium acetate, in the presence of acetic acid and acetic anhydride. The structures of the newly synthesized compounds have been confirmed by elemental analysis and spectral methods (IR, 1H-NMR, 13C-NMR, MS). The antimicrobial activity of all new compounds has been screened against some bacteria and yeasts.
在本研究中，从一些4-(4-X-苯基磺酰基)苯基)-4H-1,2,4-三唑-3-硫醇1a-c（X = H、Cl、Br）出发，合成了一系列具有桥头氮的噻唑并[3,2-b][1,2,4]三唑类新型杂环稠合体系。通过用2-溴-4'-氟苯乙酮处理三唑1a-c，得到S-烷基化的1,2,4-三唑中间体2-(5-(4-(4-X-苯基磺酰基)苯基)-2H-1,2,4-三唑-3-基硫基)-1-(4-氟苯基)乙酮2a-c。在0℃下，通过S-烷基化的1,2,4-三唑2a-c在硫酸介质中环化，得到2-(4-(4-X-苯基磺酰基)苯基)-6-(4-氟苯基)噻唑并[3,2-b][1,2,4]三唑3a-c。为了合成2-(4-(4-X-苯基磺酰基)苯基)-5-(4-氟亚苄基)-噻唑并[3,2-b][1,2,4]三唑-6(5H)-酮4a-c，在乙酸和乙酸酐存在下，用4-氟苯甲醛、氯乙酸和无水乙酸钠处理三唑1a-c。新合成化合物的结构已通过元素分析和光谱方法（红外光谱、1H-核磁共振、13C-核磁共振、质谱）得到证实。已针对一些细菌和酵母筛选了所有新化合物的抗菌活性。
