Design, Synthesis and the Biological Evaluation of New 1,3-Thiazolidine-4-ones Based on the 4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one Scaffold

Molecules

Maria Apotrosoaei¹  Ioana Mirela Vasincu¹  Maria Dragan¹  Frຝéric Buron²  Sylvain Routier² 

[1] Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy “Grigore T. Popa”, 16 University Street, Iasi 700115, Romania; E-Mails:;Institute of Organic and Analytical Chemistry, University of Orléans, Orléans 45076, Cedex 2, France; E-Mail:

关键词: 4-aminophenazone;    thiazolidine-4-one;    synthesis;    spectroscopic methods;    antioxidant effects;   

DOI  :  10.3390/molecules190913824

来源: mdpi

【 摘 要 】

New thiazolidine-4-one derivatives based on the 4-aminophenazone (4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one) scaffold have been synthesized as potential anti-inflammatory drugs. The pyrazoline derivatives are known especially for their antipyretic, analgesic and anti-inflammatory effects, but recently there were synthesized new compounds with important antioxidant, antiproliferative, anticancer and antidiabetic activities. The beneficial effects of these compounds are explained by nonselective inhibition of cyclooxygenase izoenzymes, but also by their potential scavenging ability for reactive oxygen and nitrogen species. The structure of the new compounds was proved using spectroscopic methods (FR-IR, ¹H-NMR, ¹³C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the ferric reducing antioxidant power, phosphomolydenum reducing antioxidant power, DPPH and ABTS radical scavenging assays. The chemical modulation of 4-aminophenazone (6) through linkage to thiazolidine-propanoic acid derivatives 5a–l led to improved antioxidant potential, all derivatives 7a–l being more active than phenazone. The most active compounds are the derivatives 7e, and 7k, which showed the higher antioxidant effect depending on the antioxidant assay considered.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.