Synthesis of (+/-) ibuprofen sugar derivatives.
- Author:
Ni SONG
1
;
Ying-xia LI
;
Xue SUN
;
Feng QU
Author Information
- Publication Type:Journal Article
- MeSH: Animals; Anti-Inflammatory Agents, Non-Steroidal; chemical synthesis; therapeutic use; Ibuprofen; analogs & derivatives; chemical synthesis; therapeutic use; Inflammation; drug therapy; Male; Mice; Molecular Conformation; Molecular Structure; Random Allocation
- From: Acta Pharmaceutica Sinica 2004;39(2):105-109
- CountryChina
- Language:Chinese
-
Abstract:
AIM(+/-) Ibuprofen sugar derivatives were prepared in order to decrease side-effects and increase bioavailability of (+/-) ibuprofen.
METHODSThe synthesis of derivatives were performed using 1,2:3, 4-di-O-isopropylidene-beta-D-galactopyranose, 1,3,4,5-tetra-O-acetyl-2-deoxy-2-amino-beta-D-gluctopyranose, 3,4 6-tri-O-acetyl-2-deoxy-2-N-acetyl-beta-D-gluctosylamine and 2,3,6,2',3',4',6'-hepta-O-acetyl-beta-D-lactosylamine as glycosyl donors, respectively. Target products (4, 7, 12a, 12b, 13) were obtained after deprotection.
RESULTSFive compounds (4, 7, 12a, 12b, 13) were synthesized as new compounds. The structures of all objective compounds were confirmed by 1HNMR, 13CNMR, HMQC, COSY, IR and MS.
CONCLUSIONIt was found that 12a showed better anti-inflammatory activity than (+/-) ibuprofen.
