Synthesis of methyl (E)-2 ',4 ''-thiazachalcones and their N-alkyl derivatives, photochemistry with theoretical calculations and antimicrobial activities


USTA A., YAŞAR A., Yayli N., Karaoglu Ş., YAYLI N.

TURKISH JOURNAL OF CHEMISTRY, vol.33, no.5, pp.621-632, 2009 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 33 Issue: 5
  • Publication Date: 2009
  • Doi Number: 10.3906/kim-0809-44
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.621-632
  • Keywords: Thiazachalcones, N-decyl-4-thiazaclaconium bromide, photodimerization, antimicrobial activity, STEREOSELECTIVE PHOTOCHEMISTRY, CHALCONES, DIMERIZATION, SPECTRA, NITRO

Abstract

A series of 9 new (E)-thiazachalcones (1-3), and their N-alkyl substituted derivatives (4-6), and stereoselective dimerization products (7-9) were synthesized, then tested for antimicrobial activity against all test microorganisms except Pseudomonas aeruginosa. The new compounds (1-6) without dimerization products (7-9) showed good antimicrobial property against Staphylococcus aureus, Listeria monocitogenes, and Enterococcus faecalis. The possible dimerization products of compounds (1-3) were calculated theoretically. Experimental and theoretical calculation showed that delta-truxinic type dimer is the most stable isomer.