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. 2014 Sep 4;19(9):13824-47.
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

Maria Apotrosoaei  1 , Ioana Mirela Vasincu  2 , Maria Dragan  3 , Frédéric Buron  4 , Sylvain Routier  5 , Lenuta Profire  6
Affiliations

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

Maria Apotrosoaei et al. Molecules. .

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 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.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of compounds 7.
Figure 1
Figure 1
The absorbance of the derivatives 7a–l in reference to phenazone.
Figure 2
Figure 2
The absorbance of the derivatives 7a–l in reference with phenazone.
Figure 3
Figure 3
The DPPH radical scavenging ability (%) of the derivatives 7a–l.
Figure 4
Figure 4
The ABTS radical scavenging ability (%) of the derivatives 7a–l.
See this image and copyright information in PMC

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