Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties

Authors : Hakan BEKTAŞ, Ahmet DEMİRBAŞ, Neslihan DEMİRBAŞ

Pages : 517-528

Doi:10.3906/sag-1208-65

View : 19 | Download : 9

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :2-insert ignore into journalissuearticles values(4-Amino-3-insert ignore into journalissuearticles values(4-chlorophenyl);-5-oxo-4,5--dihydro-1H-1,2,4-triazol- 1-yl);-N`-[insert ignore into journalissuearticles values(2,6-dihalogenophenyl);-methylene]acetohydrazides insert ignore into journalissuearticles values(3a,b); was obtained via the formation of 2-insert ignore into journalissuearticles values(4-amino-3-insert ignore into journalissuearticles values(4-chlorophenyl);-5-oxo-4,5- dihydro-1H-1,2,4-triazol-1-yl);acetohydrazide insert ignore into journalissuearticles values(2);, which was obtained starting from 4-amino-5-insert ignore into journalissuearticles values(4-chlo\-rophenyl);-2,4-dihydro-3H-1,2,4-triazol-3-one insert ignore into journalissuearticles values(1); in 2 steps. 2-{[4-amino-3-insert ignore into journalissuearticles values(4-chlorophenyl);-5-oxo-4,5--dihydro-1H- 1,2,4-triazol-1-yl]acetyl}-N-phenylhydra-zine carbothioamide insert ignore into journalissuearticles values(4);, which was prepared starting from 2, was converted to the corresponding 1,3,4-thiadiazole derivative insert ignore into journalissuearticles values(5); in acidic media. Moreover, the basic treatment of 4 resulted in the formation of 4-amino-5-insert ignore into journalissuearticles values(4-chlorophenyl);- 2-[insert ignore into journalissuearticles values(4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl);methyl]-2,4- dihydro-3H-1,2,4-triazol-3-one insert ignore into journalissuearticles values(7);. The reactions of compounds 5 and 7 with methyl iodide in the presence of sodium ethoxide afforded the corresponding N-methyl insert ignore into journalissuearticles values(6); and S-methyl insert ignore into journalissuearticles values(8); derivatives, respectively. The synthesis of Mannich bases insert ignore into journalissuearticles values(10a and 10b); was performed from the reaction of 7 with morpholine or piperazine in the presence of formaldehyde. All the newly synthesized compounds were screened for their antimicrobial activity. The antimicrobial activity study revealed that compounds 3a, 3b, and 5 showed good antimicrobial activities against the test microorganisms as compared with ampicillin.
Keywords : 1, 2, 4 triazol 3 one, 5 thioxo 1, 2, 4 triazole,