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, cilt.188, sa.2-3, ss.161-168, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 188 Sayı: 2-3
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1016/j.jphotochem.2006.12.004
  • Dergi Adı: JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.161-168
  • Anahtar Kelimeler: nitro(E)-3-azachalcones, nitro-(E)-N-decyl-3-azachalconium bromide, photodimerization, antimicrobial and antioxidant activities, DIMERIZATION, ESTERS
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

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.