Synthesis of S-(5-aryl-1,3,4-oxadiazol-2-yl) O-alkyl carbonothioate and alkyl 2-((5-aryl-1,3,4-oxadiazol-2-yl)thio) acetate, and their antimicrobial properties

Authors : Abdukhakim ZİYAEV, Sobirdjan SASMAKOV, Turdibek TOSHMURODOV, Mavluda ZIYAEVA, Jaloliddin ABDURAKHMANOV, Shukhrat KHASANOV, Shakhnoz AZİMOVA

Pages : 599-604

Doi:10.18596/jotcsa.1250629

View : 43 | Download : 59

Publication Date : 2023-08-30

Article Type : Research Paper

Abstract :The S-insert ignore into journalissuearticles values(5-aryl-1,3,4-oxadiazol-2-yl); O-alkyl carbonothioate insert ignore into journalissuearticles values(4-9); and the alkyl 2-insert ignore into journalissuearticles values(insert ignore into journalissuearticles values(5-aryl-1,3,4-oxadiazol-2-yl);thio); acetate insert ignore into journalissuearticles values(10-15); were synthesized by interaction of 5-aryl-1,3,4-oxadiazole-2-thiones with alkyl esters of chloroformic acid and chloroacetic acid. The yields of target compounds insert ignore into journalissuearticles values(7-9); obtained with isobutyl chloroformate were 69-73%, compounds insert ignore into journalissuearticles values(4-6); with propyl chloroformate - 74-79% and compounds insert ignore into journalissuearticles values(10-15); with alkyl esters of chloroacetic acid - 86-92%, respectively. The structures of the synthesized compounds were confirmed by IR, UV, 1H and 13C NMR spectra. The antibacterial and antifungal activities of these compounds were investigated. The results of in vitro antimicrobial activity tests showed that S-insert ignore into journalissuearticles values(5-phenylinsert ignore into journalissuearticles values(2-chlorophenyl);-1,3,4-oxadiazol-2-yl); O-propyl carbonothioate insert ignore into journalissuearticles values(4-5); and S-insert ignore into journalissuearticles values(5-phenylinsert ignore into journalissuearticles values(2-chlorophenyl);-1,3,4-oxadiazol-2-yl); O-isobutyl carbonothioate insert ignore into journalissuearticles values(7-8); exhibited weak, but selective antibacterial activity against gram-positive bacteria insert ignore into journalissuearticles values(Bacillus subtilis and Staphylococcus aureus);. At the same time, no activity was shown by compounds with two chlorine atoms in the aromatic ring insert ignore into journalissuearticles values(13-15); and alkyl 2-insert ignore into journalissuearticles values(insert ignore into journalissuearticles values(5-aryl-1,3,4-oxadiazol-2-yl); thio); acetate insert ignore into journalissuearticles values(10-15);.
Keywords : S 5 aryl 1, 3, 4 oxadiazol 2 yl, O alkyl carbonothioate, 5 aryl 1, 3, 4 oxadiazole 2 thiones, alkyl 2 5 aryl 1, 3, 4 ox