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Molecules 2014, 19(9), 13824-13847; doi:10.3390/molecules190913824

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

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.
Received: 5 August 2014 / Revised: 28 August 2014 / Accepted: 29 August 2014 / Published: 4 September 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

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 5al led to improved antioxidant potential, all derivatives 7al 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. View Full-Text
Keywords: 4-aminophenazone; thiazolidine-4-one; synthesis; spectroscopic methods; antioxidant effects 4-aminophenazone; thiazolidine-4-one; synthesis; spectroscopic methods; antioxidant effects
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Apotrosoaei, M.; Vasincu, I.M.; Dragan, M.; Buron, F.; Routier, S.; Profire, L. 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 2014, 19, 13824-13847.

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