Synthesis, configuration, and antimicrobial properties of novel substituted and cyclized '2 ',3 ''-thiazachalcones'

USTA A., Yasar A., YILMAZ N., GUELEC C., Yayh N., KARAOGLU S. A., ...More

HELVETICA CHIMICA ACTA, vol.90, no.8, pp.1482-1490, 2007 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 90 Issue: 8
  • Publication Date: 2007
  • Doi Number: 10.1002/hlca.200790154
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1482-1490
  • Karadeniz Technical University Affiliated: Yes

Abstract

Nine new thiazachalcone-based drugs, compounds I - 9, were prepared and fully characterized. The configurations of the photochemical -dimerization products 7-9 were rationalized by semi-empirical calculations. Both the experimental data and the theoretical calculations showed that the delta-truxinic acid type dimer is the most stable isomer of all. All compounds were tested for their antibacterial and antifungal activities. The N-alkylated congeners 4-6 showed strong antimicrobial activities against various bacteria and a yeast-like fungus. The MIC and MBC values were as low as 0.1 mu g/ml. All the compounds were active against the Gram-positive bacterium Staphylococcus aureas.