Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides

Authors : Canan ALBAY, Nuran KAHRİMAN, Nagihan Yilmaz İSKENDER

Pages : 441-454

Doi:10.3906/zoo-1205-26

View : 12 | Download : 5

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :In this study, 18 new N-octyl, N-decyl, and N-dodecyl substituted o-, m-, and p-methoxy insert ignore into journalissuearticles values(E);-3- and 4-azachalcones, {4- or 3-[insert ignore into journalissuearticles values(1E);-3-insert ignore into journalissuearticles values(4-, 3-, or 2-methoxyphenyl);-3-oxoprop-1-en-1-yl]-1-alkyl insert ignore into journalissuearticles values(C8,10,12); pyridinium bromides} insert ignore into journalissuearticles values(1a-6a, 1b-1b, and 1c-6c);, and 4 new o-, and m-methoxy insert ignore into journalissuearticles values(E);-3- and 4-azachalcones insert ignore into journalissuearticles values(2, 3, 5, and 6); were synthesized and tested for antimicrobial activities against Escherichia coli, Yersinia pseudotuberculosis, Enterobacter aerogenes, Pseudomonas aeruginosa, Staphylococcus aureus, Enterococcus faecalis, Bacillus cereus, and Candida albicans. N-Alkyl substituted azachalconium bromides showed good antimicrobial activity against all tested microorganisms with minimal inhibitory concentration insert ignore into journalissuearticles values(MIC); values in the range of 0.42-58.7 m g/mL in most cases. Nonalkylated compounds 1-9 were not as effective as the alkylated compounds. They showed only antimicrobial activity against gram-positive bacteria and yeast in the range of 1.77-123.7 m g/mL. The optimum length of the alkyl chain for better activity is situated with 12 carbon atoms in the series of compounds 1a-c, 2a-c, 3a-c, 4a-c, 5a-c, and 6a-c. N-Alkyl derivatives of m-methoxy insert ignore into journalissuearticles values(E);-3-azachalcone insert ignore into journalissuearticles values(4a-c, 5a-c, and 6a-c); showed better activity in comparison to those of o- and p-methoxy insert ignore into journalissuearticles values(E);-4-azachalcones insert ignore into journalissuearticles values(1a-c, 2a-c, and 3a-c);.
Keywords : N Alkyl p methyl E, 3 and 4 azachalconium bromides, antimicrobial activity