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.
Key Laboratory of Chemical Biology of Hebei Province, School of Chemistry and Environmental Science, Hebei University, Baoding, Hebei 071002, China.
Pingzhu
P
Zhang
Chao
C
Wei
Enkai
E
Wang
Wei
W
Wang
Ming
M
Liu
Qingmei
Q
Yin
Hua
H
Chen
Kerang
K
Wang
Xiaoliu
X
Li
Jinchao
J
Zhang
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors; D006801:Humans; D007555:Isoxazoles / Q000737:chemistry*; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D004187:Disaccharides; D007555:Isoxazoles; D018894:Reverse Transcriptase Inhibitors; D054303:HIV Reverse Transcriptase; D006026:Glycoside Hydrolases