Department of Pharmaceutical Chemistry, Faculty of Pharmacy, "Grigore T. Popa" University of Medicine and Pharmacy, 16 University Street, Iasi 700115, Romania.
Molecules. 2013 Aug 13;18(8):9684-703. doi: 10.3390/molecules18089684.
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).
从茶碱（1,3-二甲基黄嘌呤）出发，合成了新的噻唑烷-4-酮衍生物 7a₁₋₇、7b₁₋₇，作为潜在的抗糖尿病药物。新衍生物的结构通过光谱方法（FT-IR、¹H-NMR、¹³C-NMR）得到证实。根据铁还原能力、总抗氧化活性以及 DPPH 和 ABTS 自由基清除测定法，评估了合成化合物的体外抗氧化潜力。活性氧（ROS）和自由基被认为与多种病理事件有关，如糖尿病及其微血管和大血管并发症。通过将噻唑烷-4-酮中间体 6a、6b 与几种芳香醛缩合进行化学调节的结果是改善了抗氧化作用。所有苄叉基噻唑烷-4-酮衍生物 7a₁₋₇、7b₁₋₇均比其母体噻唑烷-4-酮更具活性。最活跃的化合物是与 4-羟基苯甲醛（化合物 7a₅、7a₆）、4-二甲氨基苯甲醛（化合物 7a₆、7b₆）和 2-硝基苯甲醛（化合物 7a₇、7b₇）缩合得到的化合物。
