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

Abstract

Abstract: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, 1 H-NMR, 13 C-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 7a 5 , 7a 6 ), 4-dimethylaminobenzaldehyde (compounds 7a 6 , 7b 6 ) and 2-nitrobenzaldehyde (compounds 7a 7 , 7b 7 ).

Thiazolidine‐4‐ones from Thiocarbohydrazides

“…The latter compounds were evaluated for their antioxidant activity using in vitro assays: ferric reducing power, total antioxidant activity, ABTS, and DPPH radical scavenging ability. The synthesized compound results support the antioxidant potential and their possible applications in several diseases mediated by reactive oxygen species including diabetes mellitus .…”

Recent Synthetic Approaches Towards Biologically Potent Derivatives/Analogues of Theophylline

“…So, keeping in view these findings, Lupascu et al . in 2013 proposed the synthesis of heterocyclic compound having thiazolidine structure linked to xanthine moiety as potential antidiabetic drug. The thiazolidine derivatives were synthesized starting from theophylline 4 , which upon three steps was converted into its 7‐acetohydrazide derivative 156 .…”

Study of N-Alkyl Derivatives of Theophylline by Gas Chromatography-Mass Spectrometry

“…Нами впервые изучено поведение при электронной ионизации (ЭИ) полученных соединений 2a, 2d, 2c, 2e, 2f, 3, 7-металлил-(2b), 7-[2-(2-хлорэтокси)этил]-(2g), 7-[2-(2гидроксиэтокси)этил]-(2h) и 7-(2,3-дибромпропил)-теофиллина (4) (схемы [1][2][3]. В масс-спектрах всех изученных соединений присутствуют пики, характерные для фрагментации теофиллина, которая была опубликована ранее в литературе [24].…”