A new method for the preparation of 5-acylidene and 5-imino substituted rhodanine derivatives and their antioxidant and antimicrobial activities

ÜNGÖREN Ş. H., ALBAYRAK S., Gunay A., Yurtseven L., Yurttas N.

TETRAHEDRON, vol.71, no.25, pp.4312-4323, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 71 Issue: 25
  • Publication Date: 2015
  • Doi Number: 10.1016/j.tet.2015.04.069
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4312-4323
  • Keywords: Rhodanines, Wittig reaction, Chalcones, Perimidines, Antioxidant activity, Antimicrobial activity, INHIBITORS, DESIGN, ACIDS
  • Yozgat Bozok University Affiliated: Yes

Abstract

Versatile syntheses of 5-imino or 5-acylidene substituted 1,3-thiazolidin-4-one derivatives are reported from alpha-dioxothiazole systems and phosphoranes via Wittig reactions. Antimicrobial and antioxidant activity of the compounds were evaluated. 5-Carbonylmethylene substituted 2-thioxo-1,3-thiazolidines have better antioxidant properties than the 5-arylimino substituted ones. The % inhibition value of the compound 3 (90.8%) was near to that of standard BHT (93.6%) at the same concentration. Compounds 5 and 15, which have the alkyliden-amide group at the C-5 position of the 1,3-thiazolidine ring showed the highest antimicrobial activities among the synthesized compounds. (C) 2015 Elsevier Ltd. All rights reserved.