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

Canan ALBAY; Nuran KAHRİMAN; Nagihan Yilmaz İSKENDER

Makale detayları

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

Yazarlar:

Canan ALBAY | Nuran KAHRİMAN | Nagihan Yilmaz İSKENDER

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2011 Vol.35 Issue 3, pp.441-454

Belge Tipi:

Makale

Yayın Tarihi:

2/2011

Belge Dili:

Türkçe

Document ID (Org No.):

2000727832

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

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 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 (E)-3-azachalcone (4a-c, 5a-c, and  6a-c) showed better activity in comparison to those of o- and  p-methoxy (E)-4-azachalcones (1a-c, 2a-c, and 3a-c).

 

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 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 (E)-3-azachalcone (4a-c, 5a-c, and  6a-c) showed better activity in comparison to those of o- and  p-methoxy (E)-4-azachalcones (1a-c, 2a-c, and 3a-c).

Makale detayları

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

Yazarlar: Canan ALBAY | Nuran KAHRİMAN | Nagihan Yilmaz İSKENDER

Yayıncı: TUBITAK

Dergi: Turkish Journal of Chemistry 2011 Vol.35 Issue 3, pp.441-454

Belge Tipi: Makale

Yayın Tarihi: 2/2011

Belge Dili: Türkçe

Document ID (Org No.): 2000727832

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Canan ALBAY | Nuran KAHRİMAN | Nagihan Yilmaz İSKENDER

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2011 Vol.35 Issue 3, pp.441-454

Belge Tipi:

Makale

Yayın Tarihi:

2/2011

Belge Dili:

Türkçe

Document ID (Org No.):

2000727832

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527