Synthesis And Biological Activity Of Thiazolidin-4-ones With A Carbohydrate Moiety

Thiazolidinone is of considerable importance as a pharmacophoric group due to their potential biological activities such as anti-virus, anti-tumor, bactericidal, anti-inflammatory etc. To the best of our knowledge, most of such compounds that have been reported concentrated on the lipophilic groups as the substituents, only a few reports on the synthesis and pharmacology of the thiazolidinones containing hydrophilic groups such as amino acid, sugar moiety have been published.taking into account the carbohydrate play an important role on the identification of biological macromolecules such as protein,In order to improve hydrophilicity of molecules and enhance affinity of cells and protein.In this paper we focused on thiazolidine-4-one with linked glycosylation as a nucleoside analogue. Hope to get some lead compounds with good biological activity in anti-virus, anti-tumor for drug development.1,Synthesis and biological activity of novel thiazolidin-4-ones with a carbohydrate moietySome novel 2-aryl-3-[5-deoxy-1,2-O-isopropylidene-a-D-xylofuranose-5-C-yl] thiazolidin-4-ones were synthesized by the three-component condensation of 5-amino-5-deoxy-1,2-O-isopropylidene-a-D-xylofuranose 41,aromatic aldehyde, and mercaptoacetic acid in the presence of DCC and DMAP at room temperature. Two diastereoisomers 44 and 45 were afforded as the main products in totally isolated yields of 25.4-70%.The structures of the new compounds were determined by NMR spectroscopy and mass spectrometry (MS), and the configuration in thiazolidin-4-one ring was tentatively assigned based on the X-ray crystallographic structure of 54d and the comparison of their corresponding NMR signals. The antitumor (human cervical cancer cells) activity and the inhibition against the glycosidases (a-glucosidase,β-glucosidase,α-amylase) have been evaluated for the new compounds, some of which exhibited antitumor activity.2,Synthesis and biological activity of novel thiazolidin-4-ones with disaccharide moiety use of Staudinger/Aza-Wittig reactionDerivatives of azido-glucopyranose and furaldehyde were synthesized use of Glucose and ribose as raw material, synthesis of novel 4-thiazolidinone linked disaccharides by tandem Staudinger/aza-Wittig/cyclization in the presence of nitrine, aldehyde, and mercaptoacetic acid at room temperature. The main products in totally isolated yields of 60%.The deprotection of acetyl was on the condition of sodium methoxide.Discussion the influences of temperature on the elimination of the acetyl, The structures of the new compounds 54 and 55 were determined by NMR spectroscopy and mass spectrometry (MS), and the configuration of the newly generated chiral carbon (C-2) in the thiazolidin-4-one ring was tentatively assigned based on the X-ray crystallographic structure of 54a-4 and 54d-3, and the comparison of their corresponding NMR signals.The antitumor (human cervical cancer cells) activity, the inhibition against thereverse transcriptase and the inhibition against the glycosidases (a-glucosidase, B-glucosidase,a-amylase)have been evaluated for the new compounds 55, but none of the compounds had any inhibitory activity.