The synthesis and the biological evaluation of new thiazolidin-4-one derivatives containing a xanthine moiety.
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).
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, "Grigore T. Popa" University of Medicine and Pharmacy, 16 University Street, Iasi 700115, Romania.
Florentina Geanina
FG
Lupascu
Oana Maria
OM
Dragostin
Liliana
L
Foia
Dan
D
Lupascu
Lenuta
L
Profire
D000975:Antioxidants / Q000378:metabolism; D001547:Benzaldehydes / Q000138:chemical synthesis* / Q000494:pharmacology; D005609:Free Radicals / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D017550:Spectroscopy, Fourier Transform Infrared; D013329:Structure-Activity Relationship; D019820:Xanthine / Q000138:chemical synthesis* / Q000494:pharmacology
D000975:Antioxidants; D001547:Benzaldehydes; D005609:Free Radicals; D019820:Xanthine; C043850:2-nitrobenzaldehyde; C011483:4-hydroxybenzaldehyde