Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives

Authors : Seda FANDAKLI, Serap BAŞOĞLU, Hakan BEKTAŞ, Meltem YOLAL

Pages : 567-582

Doi:10.3906/yer-1207-3

View : 26 | Download : 7

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Ethyl[4-arylmethyleneamino-3-insert ignore into journalissuearticles values(4-metylphenyl);-5-oxo-4,5-dihydro- 1H-1,2,4-triazole-1-yl]acetates insert ignore into journalissuearticles values(3a-e and 10a-d); were obtained starting from 4-amino-2,4-dihydro-3H-1,2,4-triazol-3-ones insert ignore into journalissuearticles values(1 and 9); in 2 steps. The treatment of 3a-e with NaBH4 resulted in the formation of 3 kinds of product incorporating carboxcilic acid insert ignore into journalissuearticles values(4a-c); or alcohol insert ignore into journalissuearticles values(5a-e); functionality. [4-{[insert ignore into journalissuearticles values(4-Methoxyphenyl);methylene]amino}- and 4-{[pyridin-4-ylmethylene]amino}-3-insert ignore into journalissuearticles values(4-methylphenyl);-5-oxo-4,5-dihydro-1H- 1,2,4-triazole-1-yl] acetic acids insert ignore into journalissuearticles values(6a, 6e); were obtained by the hydrolysis of the corresponding esters insert ignore into journalissuearticles values(5a-5e);. The treatment of 6a with NaBH4 caused the reduction of only the imine bond; the carboxyl group remained unchanged. Then this carboxylic acid was converted to the corresponding hydrazide insert ignore into journalissuearticles values(8); in 2 steps by reaction with ethanol and hydrazine hydrate, respectively. The synthesis of Mannich bases was performed by the reaction of the corresponding 1,2,4-triazoles containing an imine group insert ignore into journalissuearticles values(10a-d); with several primary or secondary amines including morpholine or piperazine nucleus. All newly synthesized compounds were screened for their antimicrobial activity. The antimicrobial activity study revealed that the Mannich bases insert ignore into journalissuearticles values(11-16); showed good activity against the test microorganisms as compared with ampicillin.
Keywords : 1, 2, 4 Triazole 3 one, reduction, hydrolysis, Mannich base, antimicrobial activity