TY  - JOUR
TI  - Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides
AB  - In this study, 18 new N-octyl, N-decyl, and N-dodecyl substituted o-, m-, and p-methoxy (E)-3- and 4-azachalcones, {4- or 3-[(1E) -3-(4-, 3-, or 2-methoxyphenyl)-3-oxoprop-1-en-1-yl]-1-alkyl (C8,10,12) pyridinium bromides} (1a-6a, 1b-1b,and 1c-6c), and 4 new o-, and m-methoxy (E) -3- and 4-azachalcones (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 (MIC) values in the range of 0.42-58.7 μg/mL in most cases. Nonalkylated compounds 1-9 werenotaseffectiveasthe alkylated compounds. They showed only antimicrobial activity against gram-positive bacteria and yeast in the range of 1.77-123.7 μg/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 (E) -3-azachalcone (4a-c, 5a-c,and 6a-c)showedbetteractivityincomparisontothoseof o- and p-methoxy (E) -4-azachalcones (1a-c, 2a-c,and 3a-c).
AU  - Alpay Karaoğlu, Şengül
AU  - Kahriman, Nuran
AU  - ALBAY, CANAN
AU  - ISKENDER, Nagihan Yılmaz
AU  - YAYLI, Nurettin
PY  - 2011
JO  - Turkish Journal of Chemistry
VL  - 35
IS  - 3
SN  - 1300-0527
SP  - 441
EP  - 454
DB  - TRDizin
UR  - http://search/yayin/detay/116563
ER  -