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

Alpay Karaoğlu, Şengül; Kahriman, Nuran; ALBAY, CANAN; ISKENDER, Nagihan Yılmaz; YAYLI, Nurettin

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

Canan ALBAY, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Nuran KAHRİMAN, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Nagihan Yılmaz ISKENDER, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Şengül Alpay KARAOĞLU, (Rize Üniversitesi, Fen Edebiyat Fakültesi, Biyoloji Bölümü, Rize, Türkiye)

Nurettin YAYLI (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Giresun, Türkiye)

Turkish Journal of Chemistry

1 0

Yıl: 2011 Cilt: 35 Sayı: 3 Sayfa Aralığı: 441 - 454 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

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

Öz:

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).

Anahtar Kelime:

Konular: Mühendislik, Kimya

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

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APA	ALBAY C, Kahriman N, ISKENDER N, Alpay Karaoğlu Ş, YAYLI N (2011). Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides. , 441 - 454.
Chicago	ALBAY CANAN,Kahriman Nuran,ISKENDER Nagihan Yılmaz,Alpay Karaoğlu Şengül,YAYLI Nurettin Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides. (2011): 441 - 454.
MLA	ALBAY CANAN,Kahriman Nuran,ISKENDER Nagihan Yılmaz,Alpay Karaoğlu Şengül,YAYLI Nurettin Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides. , 2011, ss.441 - 454.
AMA	ALBAY C,Kahriman N,ISKENDER N,Alpay Karaoğlu Ş,YAYLI N Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides. . 2011; 441 - 454.
Vancouver	ALBAY C,Kahriman N,ISKENDER N,Alpay Karaoğlu Ş,YAYLI N Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides. . 2011; 441 - 454.
IEEE	ALBAY C,Kahriman N,ISKENDER N,Alpay Karaoğlu Ş,YAYLI N "Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides." , ss.441 - 454, 2011.
ISNAD	ALBAY, CANAN vd. "Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides". (2011), 441-454.

APA	ALBAY C, Kahriman N, ISKENDER N, Alpay Karaoğlu Ş, YAYLI N (2011). Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides. Turkish Journal of Chemistry, 35(3), 441 - 454.
Chicago	ALBAY CANAN,Kahriman Nuran,ISKENDER Nagihan Yılmaz,Alpay Karaoğlu Şengül,YAYLI Nurettin Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides. Turkish Journal of Chemistry 35, no.3 (2011): 441 - 454.
MLA	ALBAY CANAN,Kahriman Nuran,ISKENDER Nagihan Yılmaz,Alpay Karaoğlu Şengül,YAYLI Nurettin Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides. Turkish Journal of Chemistry, vol.35, no.3, 2011, ss.441 - 454.
AMA	ALBAY C,Kahriman N,ISKENDER N,Alpay Karaoğlu Ş,YAYLI N Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides. Turkish Journal of Chemistry. 2011; 35(3): 441 - 454.
Vancouver	ALBAY C,Kahriman N,ISKENDER N,Alpay Karaoğlu Ş,YAYLI N Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides. Turkish Journal of Chemistry. 2011; 35(3): 441 - 454.
IEEE	ALBAY C,Kahriman N,ISKENDER N,Alpay Karaoğlu Ş,YAYLI N "Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides." Turkish Journal of Chemistry, 35, ss.441 - 454, 2011.
ISNAD	ALBAY, CANAN vd. "Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides". Turkish Journal of Chemistry 35/3 (2011), 441-454.