Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

Molecules

Ioana Mirela Vasincu¹  Maria Apotrosoaei¹  Andreea-Teodora Panzariu¹  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: ibuprofen;    thiazolidine-4-one;    synthesis;    spectral methods;    antioxidant effect;   

DOI  :  10.3390/molecules190915005

来源: mdpi

【 摘 要 】

New thiazolidine-4-one derivatives of 2-(4-isobutylphenyl)propionic acid (ibuprofen) have been synthesized as potential anti-inflammatory drugs. The structure of the new compounds was proved using spectral methods (FR-IR, ¹H-NMR, ¹³C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the total antioxidant activity, the DPPH and ABTS radical scavenging assays. Reactive oxygen species (ROS) and free radicals are considered to be involved in many pathological events like diabetes mellitus, neurodegenerative diseases, cancer, infections and more recently, in inflammation. It is known that overproduction of free radicals may initiate and amplify the inflammatory process via upregulation of genes involved in the production of proinflammatory cytokines and adhesion molecules. The chemical modulation of acyl hydrazones of ibuprofen 3a–l through cyclization to the corresponding thiazolidine-4-ones 4a–n led to increased antioxidant potential, as all thiazolidine-4-ones were more active than their parent acyl hydrazones and also ibuprofen. The most active compounds are the thiazolidine-4-ones 4e, m, which showed the highest DPPH radical scavenging ability, their activity being comparable with vitamin E.

【 授权许可】

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