Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides.
Xiang-Bao Meng, Dong Han, Su-Na Zhang, Wei Guo, Jing-Rong Cui, Zhong-Jun Li
文献索引:Carbohydr. Res. 342(9) , 1169-74, (2007)
全文:HTML全文
摘要
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).
相关化合物
相关文献:
2015-07-13
[Biomacromolecules 16 , 1948-57, (2015)]
2015-03-20
[Carbohydr. Res. 405 , 33-8, (2015)]
2015-04-20
[Carbohydr. Polym. 120 , 7-14, (2015)]
2012-01-01
[Steroids 77(1-2) , 59-66, (2012)]
2015-10-28
[ACS Appl. Mater. Interfaces 7 , 23633-43, (2015)]