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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

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 7al in reference to phenazone.
Figure 2
Figure 2
The absorbance of the derivatives 7al in reference with phenazone.
Figure 3
Figure 3
The DPPH radical scavenging ability (%) of the derivatives 7al.
Figure 4
Figure 4
The ABTS radical scavenging ability (%) of the derivatives 7al.

References

    1. Jamwal A., Javed A., Bhardwaj V. A review on pyrazole derivatives of pharmacological potential. J. Pharm. BioSci. 2013;3:114–123.
    1. El-Hawash S., Badawey E.-S., El-Ashmawey I. Nonsteroidal antiinflammatory agents-part 2. Antiinflammatory, analgesic and antipyretic activity of some substituted 3-pyrazolin-5-ones and 1,2,4,5,6,7-3H-hexahydroindazol-3-ones. Eur. J. Med. Chem. 2006;41:155–165. doi: 10.1016/j.ejmech.2005.09.006. - DOI - PubMed
    1. Le Bourdonnec B., Meulon E., Yous S., Goossens J.-F., Houssin R., Hénichart J.-P. Synthesis and pharmacological evaluation of new pyrazolidine-3,5-diones as AT1 angiotensin II receptor antagonists. J. Med. Chem. 2000;43:2685–2697. doi: 10.1021/jm9904147. - DOI - PubMed
    1. El-Sayed M.A., Abdel-Aziz N.I., Abdel-Aziz A.A., El-Azab A.S., ElTahir K.E. Synthesis, biological evaluation and molecular modeling study of pyrazole and pyrazoline derivatives as selective COX-2 inhibitors and anti-inflammatory agents. Bioorg. Med. Chem. 2012;20:3306–3316. doi: 10.1016/j.bmc.2012.03.044. - DOI - PubMed
    1. Fushimi N., Fujikura H., Shiohara H., Teranishi H., Shimizu K., Yonekubo S., Ohno K., Miyagi T., Itoh F., Shibazaki T., et al. Structure-activity relationship studies of 4-benzyl-1H-pyrazol-3-yl β-d-glucopyranoside derivativesas potent and selective sodium glucose co-transporter 1 (SGLT1) inhibitors with therapeutic activity on postprandial hyperglycemia. Bioorg. Med. Chem. 2012;20:6598–6612. doi: 10.1016/j.bmc.2012.09.037. - DOI - PubMed

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