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

Molecules

Florentina Geanina Lupascu²  Oana Maria Dragostin²  Liliana Foia¹  Dan Lupascu² 

[1] Department of Biochemistry, Faculty of Dentistry, “Grigore T. Popa” University of Medicine and Pharmacy, 16 University Street, Iasi 700115, Romania; E-Mail:;Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Grigore T. Popa” University of Medicine and Pharmacy, 16 University Street, Iasi 700115, Romania; E-Mails:

关键词: thiazolidin-4-one;    xanthine;    synthesis;    spectral methods;    antioxidant effect;   

DOI  :  10.3390/molecules18089684

来源: mdpi

【 摘 要 】

Starting from theophylline (1,3-dimethylxanthine) new thiazolidin-4-one derivatives 7a_1–7, 7b_1–7 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 7a_1–7, 7b_1–7 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).

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.