Synthesis and antimicrobial activities of 2-(5-mercapto)-1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives

Authors : Ahmet DEMİRBAŞ, Deniz ŞAHİN, Neslihan DEMİRBAŞ

Pages : 347-358

View : 17 | Download : 12

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :The synthesis of 4-amino-2-[insert ignore into journalissuearticles values(5-mercapto-1,3,4-oxadiazol-2- yl);methyl]-5-insert ignore into journalissuearticles values(4-methylphenyl);-2,4-dihydro-3H-1,2,4-triazol-3-one insert ignore into journalissuearticles values(2); and 4-amino-2-[insert ignore into journalissuearticles values(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl);methyl]- 5-insert ignore into journalissuearticles values(4-methylphenyl);-2,4-dihydro-3H-1,2,4-triazol-3-one insert ignore into journalissuearticles values(5); was performed starting from 2-[4-amino-3-insert ignore into journalissuearticles values(4-methylphenyl);-5-oxo-4,5- dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide insert ignore into journalissuearticles values(1);. The treatment of 2 and 5 with 4-fluorobenzaldehyde insert ignore into journalissuearticles values(for 8); or salicylaldehyde insert ignore into journalissuearticles values(for 6); afforded the corresponding Schiff bases insert ignore into journalissuearticles values(6 and 8);. The condensation of 5 with phenacyl bromide produced 4-amino-5-insert ignore into journalissuearticles values(4-methylphenyl);-2- [insert ignore into journalissuearticles values(6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl);methyl]- 2,4-dihydro-3H-1,2,4-triazol-3-one insert ignore into journalissuearticles values(7);. The alkylation of 2 and 8 was carried out by using methyl iodide in basic media. Compounds 3 and 10a,b were prepared by aminoalkylation of 2 and 8 with 4-fluorophenyl piperazine, morpholine, or 4-methyl piperazine in the presence of formaldehyde. The synthesized compounds were screened for their antimicrobial activities and, with the exception of 2, 4, 7, and 9, were found to possess good or moderate activities against the screened bacterial strains except Candida tropicalis and Candida albicans.
Keywords : 1, 2, 4 Triazole, 1, 3, 4 oxadiazole, Mannich base, antimicrobial activity