Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides.
3,4,6-Tri-O-acetyl-D-galactal, 3,4,6-tri-O-acetyl-D-glucal and 3,6,2',3',4'6'-hexa-O-acetyl-D-lactal were reacted with N-hydroxymethylphthalimide and boron trifluoride etherate to produce the corresponding phthalimidomethyl unsaturated glycosides via Ferrier rearrangement. When the galactal derivative was used, a non-Ferrier rearrangement product was also isolated as a minor product under classical Ferrier conditions. Phthalimidomethyl deoxy glycosides were readily prepared by hydrogenation of the unsaturated glycosides. Following deacetylation, the anti-inflammatory activities of these compounds were tested on mice and three were found to possess potent activity compared to hydrocortisone sodium succinate (HSS).
Meng
Xiang-Bao
XB
Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China.
Han
Dong
D
Zhang
Su-Na
SN
Guo
Wei
W
Cui
Jing-Rong
JR
Li
Zhong-Jun
ZJ
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001880:Boranes / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003837:Deoxy Sugars / Q000737:chemistry; D004195:Disease Models, Animal; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007249:Inflammation / Q000188:drug therapy; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry
D000893:Anti-Inflammatory Agents; D001880:Boranes; D003837:Deoxy Sugars; D006027:Glycosides; D010797:Phthalimides; C101707:boron trifluoride etherate; C039968:N-hydroxymethylphthalimide