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

Vasincu, Ioana Mirela; Apotrosoaei, Maria; Panzariu, Andreea-Teodora; Buron, Frédéric; Routier, Sylvain; Profire, Lenuta

doi:10.3390/molecules190915005

Open AccessArticle

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

by

Ioana Mirela Vasincu

¹

,

Maria Apotrosoaei

¹,

Andreea-Teodora Panzariu

¹,

Frédéric Buron

²

,

Sylvain Routier

^2,* and

Lenuta Profire

^1,*

¹

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, Iasi 700115, Romania

²

Institute of Organic and Analytical Chemistry, University of Orléans, Orléans 45076, Cedex 2, France

^*

Authors to whom correspondence should be addressed.

Molecules 2014, 19(9), 15005-15025; https://doi.org/10.3390/molecules190915005

Submission received: 3 July 2014 / Revised: 21 August 2014 / Accepted: 10 September 2014 / Published: 18 September 2014

(This article belongs to the Section Medicinal Chemistry)

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Abstract

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.

Keywords: ibuprofen; thiazolidine-4-one; synthesis; spectral methods; antioxidant effect

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MDPI and ACS Style

Vasincu, I.M.; Apotrosoaei, M.; Panzariu, A.-T.; Buron, F.; Routier, S.; Profire, L. Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid. Molecules 2014, 19, 15005-15025. https://doi.org/10.3390/molecules190915005

AMA Style

Vasincu IM, Apotrosoaei M, Panzariu A-T, Buron F, Routier S, Profire L. Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid. Molecules. 2014; 19(9):15005-15025. https://doi.org/10.3390/molecules190915005

Chicago/Turabian Style

Vasincu, Ioana Mirela, Maria Apotrosoaei, Andreea-Teodora Panzariu, Frédéric Buron, Sylvain Routier, and Lenuta Profire. 2014. "Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid" Molecules 19, no. 9: 15005-15025. https://doi.org/10.3390/molecules190915005

APA Style

Vasincu, I. M., Apotrosoaei, M., Panzariu, A.-T., Buron, F., Routier, S., & Profire, L. (2014). Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid. Molecules, 19(9), 15005-15025. https://doi.org/10.3390/molecules190915005

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

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