Microwave-Assisted Synthesis of 1,4′-Diazaflavone and N-Alkyl Derivative Pigments with Anti-Microbial Activity

Yayli N., Üçüncü O., Yaylı N., Demir E., Demirbağ Z.

Turkish Journal of Chemistry, cilt.32, sa.6, ss.785-795, 2008 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 32 Sayı: 6
  • Basım Tarihi: 2008
  • Dergi Adı: Turkish Journal of Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.785-795
  • Anahtar Kelimeler: 1,4′-diazaflavone, Anti-microbial activity, Aza-chalcone, Microwave-assisted, N-alkyl-1,4′-diazaflavonium bromide, Pigment (3-12)
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

1,4′-Diazaflavone pigment (2) was synthesized by a simple environmentally friendly microwave-assisted one-pot method for the cyclization of 2′-amino (E)-4″-aza-chalcone (1) under solventless conditions using K-10 clay. In addition, 10 new N-alkyl (C5-12,14-15) substituted 1,4′-diazaflavonium bromide pigments (3-12) were prepared from compound 2 or directly from compound 1, with corresponding alkyl halides in acetonitrile under reflux. The anti-microbial activity of compounds 1-12 was tested. The N-alkyl substituted 1,4′-diazaflavonium bromides (3-12) showed good antimicrobial activity against the gram-positive bacteria tested with minimal bactericidal concentration (MBC) values for the reference antibiotic kanamycin. The optimum length of the alkyl chain for better and broader activity was 6-10 carbon atoms in the series of compounds (3-12).