Synthesis, antibacterial and antioxidant activities of new 1-alkyl-4-(1-alkyl-4-oxo-1,4-dihydroquinolin-2-yl)pyridinium bromides

KAHRİMAN N., Yayli B., AKTAS A., ISKEFIYELI Z., BERIS F. S., YAYLI N.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, cilt.69, ss.348-355, 2013 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 69
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1016/j.ejmech.2013.08.050
  • Dergi Adı: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.348-355
  • Anahtar Kelimeler: Microwave, 1,4 '-Diazaflavone, Quinoline nucleus, N,N '-Dialkyl-1,4 '-diazaflavonium bromide, Antibacterial activity, Antioxidant activity, MICROWAVE-ASSISTED SYNTHESIS, SOLVENT-FREE SYNTHESIS, N-ALKYL DERIVATIVES, CORRESPONDING 2-ARYL-2,3-DIHYDROQUINOLIN-4(1H)-ONES, ANTIMICROBIAL PROPERTIES, FUNCTIONALIZED FLAVONES, BIOLOGICAL-ACTIVITIES, TEA POLYPHENOLS, CYCLIZATION, FACILE
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

New 1-alkyl-4-(1-alkyl-4-oxo-1,4-dihydroquinolin-2-yl)pyridinium bromides (3a k) were synthesized from 1,4'-diazaflavone [2-pyridin-4-ylquinolin-4(1H)-one] and evaluated for antibacterial and antioxidant activities. A rapid one-pot preparation of 1,4'-diazaflavone (2) was done from 2'-amino substituted chalcone (1) by intramolecular Michael addition using solvent-free microwave heating. New N,N'-dialkyl substituted (C-5-C-15) 1,4'-diazaflavonium bromides were synthesized from compound 2 with corresponding alkyl halides. Compounds 3a k were active against six bacteria (MIC: 7.8-500.0 mu g/mL). They also showed good antioxidant activities in DPPI-1* scavenging (SC50: 45-133 mu g/mL) and ferric reducing/antioxidant power (14-141 p.M TEAC) tests. The biological activities decreased as alkyl chain length increased. The reason behind the obvious negative effect of alkyl chain elongation is unclear and requires investigations about the intermolecular interactions of these pyridinium salts with bioassay components. (C) 2013 Elsevier Masson SAS. All rights reserved.