Synthesis and biological activities of novel isoxazoline-linked pseudodisaccharide derivatives

A series of novel isoxazoline linked pseudodisaccharide derivatives were regiospecifically synthesized by 1,3-dipolar cycloaddition of α-allyl-C-glycopyranosides and sugar-derived nitrile oxides with good yields. The structures of the compounds were characterized by NMR spectroscopy and MS spectrometry and confirmed by the X-ray crystallographic analysis of compound ((5S)-3-(2,3-O-isopropylidene-5-deoxy-d-lyxofuranose-4-yl)isoxazoline-5-yl) methyl α- C-d-galactopyranoside. Their biological activities against glycosidases (α-amylase, α-glucosidase, and β-glucosidase) and HIV-RT, and antitumor activity were preliminarily evaluated. Some of them exhibited potent inhibitory activity to HIV-RT.

Graphical abstractA series of novel isoxazoline linked pseudodisaccharide derivatives have been regiospecifically synthesized in good yields by 1,3-dipolar cycloaddition. Some compounds exhibited very good inhibitory activity to HIV-RT.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Novel isoxazoline linked pseudodisaccharide derivatives. ► 1,3-Dipolar cycloaddition reaction of α-allyl-C-glycopyranosides to nitrile oxides. ► Establish compounds configuration by NMR analysis and X-ray crystallography. ► Very good HIV-RT inhibitors.