Molecules 2013, 18(8), 9684-9703; doi:10.3390/molecules18089684
Article

The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety

Received: 10 July 2013; Accepted: 5 August 2013 / Published: 13 August 2013
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: Starting from theophylline (1,3-dimethylxanthine) new thiazolidin-4-one derivatives 7a1–7, 7b1–7 have been synthesized as potential antidiabetic drugs. The structure of the new derivatives was confirmed using spectral methods (FT-IR, 1H-NMR, 13C-NMR). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the ferric reducing power, the total antioxidant activity and the DPPH and ABTS radical scavenging assays. Reactive oxygen species (ROS) and free radicals are considered to be implicated in a variety of pathological events, such as diabetes mellitus and its micro- and macrovascular complications. The results of chemical modulation of the thiazolidin-4-one intermediaries 6a, 6b through condensation with several aromatic aldehydes is the improvement of the antioxidant effect. All benzylidenethiazolidin-4-one derivatives 7a1–7, 7b1–7 are more active than their parent thiazolidin-4-ones. The most active compounds are the ones obtained by reaction of condensation with 4-hydroxybenzaldehyde (compounds 7a5, 7a6), 4-dimethylaminobenzaldehyde (compounds 7a6, 7b6) and 2-nitrobenzaldehyde (compounds 7a7, 7b7).
Keywords: thiazolidin-4-one; xanthine; synthesis; spectral methods; antioxidant effect
PDF Full-text Download PDF Full-Text [440 KB, uploaded 18 June 2014 20:09 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

Lupascu, F.G.; Dragostin, O.M.; Foia, L.; Lupascu, D.; Profire, L. The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety. Molecules 2013, 18, 9684-9703.

AMA Style

Lupascu FG, Dragostin OM, Foia L, Lupascu D, Profire L. The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety. Molecules. 2013; 18(8):9684-9703.

Chicago/Turabian Style

Lupascu, Florentina G.; Dragostin, Oana M.; Foia, Liliana; Lupascu, Dan; Profire, Lenuta. 2013. "The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety." Molecules 18, no. 8: 9684-9703.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert