Synthesis and biological activities of N-alkyl derivatives of o-, m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations

YAYLI N., UCUNCU O., YASAR A., KUCUK M., YAYLI N., Akyuz E., ...More

TURKISH JOURNAL OF CHEMISTRY, vol.30, no.4, pp.505-514, 2006 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 30 Issue: 4
  • Publication Date: 2006
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.505-514
  • Keywords: nitro-(E)-4-azachalcones, nitro-(E)-N-decyl-4-azachalconium bromide, photodimerisation, antimicrobial and antioxidant activities, DIMERIZATION, CHALCONES
  • Recep Tayyip Erdoğan University Affiliated: No

Abstract

The N-alkyl derivatisation and photochemical dimerisation of 3 o-, m-, and p-nitro substituted 4-azachalcones (1-3) yielded 3 new o-, m-, and p-nitro substituted (E)-N-decyl-4-azachalconium bromides, (2E)-1-(2-nitrophenyl)-3-(N-decyl-4-pyridinium bromide)-2-propen-1-one (4), (2E)-1-(3-nitrophenyl)3-(N-decyl-4-pyridinium bromide)-2-propen-1-one (5), and (2E)-1-(4-nitrophenyl)-3-(N-decyl-4-pyridinium bromide)-2-propen-1-one (6), and 3 new dimers in solution, (1 beta,2 alpha)-di-(3-nitrobenzoyl)-(3 beta,4 alpha)-di(4-pyridinyl)cyclobutane (7), (1 beta,2 alpha)-di-(4-nitrobenzoyl)-(3 beta,4 alpha)-di-(4-pyridinyl)cyclobutane (8a), and (1 beta,2 beta)-di-(4-nitrobenzoyl)-(3 beta,4 alpha)-di-(4-pyridinyl)cyclobutane (8b), stereoselectively. The monomeric compounds showed good antimicrobial activity against test micro-organisms. The most sensitive microorganisms were Gram-positive bacteria. The monomers also showed high antioxidant activity, while the dimerisation products 7-8a,b were less active. Compound 6 was found to have similar or even higher activity when compared to the standard antioxidants Trolox((R)) and vitamin C, respectively. The possible dimerisation products of compounds 1-3 were calculated theoretically. Experimental and theoretical calculations showed that delta-truxinic type dimer is the most stable isomer.