Synthesis of N-alkyl derivatives and photochemistry of nitro (E)-3-azachalcones with theoretical calculations and biological activities

Yayli N., Kucuk M., Ucuncu O., Yasar A., YAYLI N., KARAOGLU S. A.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, vol.188, no.2-3, pp.161-168, 2007 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 188 Issue: 2-3
  • Publication Date: 2007
  • Doi Number: 10.1016/j.jphotochem.2006.12.004
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.161-168
  • Keywords: nitro(E)-3-azachalcones, nitro-(E)-N-decyl-3-azachalconium bromide, photodimerization, antimicrobial and antioxidant activities, DIMERIZATION, ESTERS
  • Karadeniz Technical University Affiliated: Yes


Three new N-alkyl substituted nitro (E)-3-azachalconium bromides (4-6) and two new stereoselective dimerization products (7 and 8) of o-, m-, and p-nitro substituted (E)-3-azachalcones were synthesized and tested for antimicrobial and antioxidant activities. Compounds 4-6 showed very good antimicrobial activities against Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Bacillus cereus, and Candida tropicalis and no activity against Klebsiella pneumoniae and Yersinia pseudotuberculosis. The monomers of o-, m-, and p-nitro substituted (E)-3-azachalcones (1-3) and their N-alkyl derivatives (4-6) showed good DPPH radical scavenging activity with IC50 values in the range of 0.25-0.90 mg/mL. The dimerization product 8 showed the highest activity among the eight compounds synthesized, while compound 7 was inactive in DPPH test. Compounds 4 and 8 showed similar antioxidant activity as the standard antioxidants Trolox (R) and Vitamin C.