Synthesis and biological activities of methylenebis-4H -1,2,4-triazole derivatives

Authors : Yıldız UYGUN, Hacer BAYRAK, Havva ÖZKAN

Pages : 812-823

Doi:10.3906/kim-1212-66

View : 12 | Download : 6

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :5,5`-Methylenebisinsert ignore into journalissuearticles values(4--phenyl-4H-1,2,4-triazole-3-thiol); insert ignore into journalissuearticles values(2); was synthesized starting from hydrazinecarbothioamide compound insert ignore into journalissuearticles values(1);. Treatment of compound 2 with ethyl bromoacetate produced diethyl 5,5`-{methylenebis[insert ignore into journalissuearticles values(4-phenyl-4H-1,2,4-triazole-5,3-diyl);thio]}diacetate insert ignore into journalissuearticles values(3);, which was converted to the corresponding diacetohydrazide derivative insert ignore into journalissuearticles values(4); by treatment with hydrazine hydrate. The reaction of compound 4 with several aldehydes produced the corresponding arylidene hydrazides, 5a--d. Syntheses of Mannich bases 6a--c were carried out by the treatment of compound 2 with several amines in the presence of formaldehyde. insert ignore into journalissuearticles values(4{[5-insert ignore into journalissuearticles values({5-[insert ignore into journalissuearticles values(4-Amino-2-chlorophenyl);thio]-4-phenyl-4H-1,2,4-triazol-3-ylmethyl);-4-phenyl-4H-1,2,4-triazol-3-yl]thio}-3-chlorophenyl);amine insert ignore into journalissuearticles values(8); was prepared by reduction of 2 nitro groups of 3,3` -methylenebis{5-[insert ignore into journalissuearticles values(2-chloro-4-nitrophenyl);thio]-4-phenyl-4H-1,2,4-triazole} insert ignore into journalissuearticles values(7); that were obtained from the condensation of 2} with 3,4-dichloronitrobenzene. The newly synthesized compounds were screened for their antimicrobial activities; some of them were found to be active towards the test microorganisms as the results demonstrated that the synthesized compounds exhibited a broad spectrum of activity with minimum inhibitory concentration insert ignore into journalissuearticles values(MIC); values of 31.3--500 m g/mL against gram-positive and gram-negative bacteria, Candia albicans and Saccharomyces cerevisiae. All compounds displayed lower activity in this series against the microorganisms with MIC values of 31.3--500 m g/mL than did the compared control drugs of ampicillin, streptomycin, and fluconazole.
Keywords : 1, 2, 4 Triazole, morpholine, furan, Schiff base, Mannich base, antimicrobial activity