Synthesis of a novel series of [1,5]-benzothiazepine-C-β-D-glycoside derivatives in a facile one-pot method and insight into their anti-oxidant properties

• Published in: Journal of molecular structure 2023-06, Vol.1281, p.135138, Article 135138
• Main Authors: Pradhan, Sheersha, Muthuvel, Panneerselvam, Mohan Das, Thangamuthu
• Format: Article
• Language: English
• Subjects: 4,6-O-Butylidene-D-glucopyranose; a-,b-unsaturated-b-C-glycosidic ketones; Anti-oxidant, DPPH; Benzothiazepine
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.135138

•A novel class of [1,5]-benzothiazepine-C-β-D-glycosides was synthesized from α, β-unsaturated- β -C-glycosidic ketones in a facile one-pot method.•The overall characterization of the synthesized products was done using NMR and elemental analyses.•The β-anomeric form of the products was supported by 1H NMR spectroscopic data.•The [1,5]-benzothiazepine-β-C-glycoside with 1,3-benzodioxole-substitution (compound 10d) showed excellent anti-oxidant characteristics at all concentrations ranging from 100 to 600 μg/mL. The development of seven-membered heterocyclic scaffolds, namely benzothiazepine, has gained much recognition in mild environmentally friendly conditions such as low temperature and short reaction time due to its vast medicinal pertinence. A novel class of [1,5]-benzothiazepine-C-β-D-glycosides was synthesized in a facile one-pot method from α, β-unsaturated-b-C-glycosidic ketones where the use of p-TSA had shown a better result. The β-anomeric forms of the C-glycosidic compounds were assigned from 1H NMR spectroscopy. Studies propose that the series of [1,5]-benzothiazepine-based β-C-glycosides showed moderate anti-oxidant activities with maximum inhibitory activity of 60%. The second generation [1,5]-benzothiazepine-β-C-glycoside (piperonal derivative) with 1,3-benzodioxole-substitution (compound 10d) especially showed excellent anti-oxidant characteristics at all concentrations ranging from 100 to 600 μg/mL. [Display omitted]