[Synthesis of (+/-) ibuprofen sugar derivatives].
OBJECTIVE
(+/-) Ibuprofen sugar derivatives were prepared in order to decrease side-effects and increase bioavailability of (+/-) ibuprofen.


METHODS
The 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.


RESULTS
Five 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.


CONCLUSIONS
It was found that 12a showed better anti-inflammatory activity than (+/-) ibuprofen.
Song
Ni
N
Institute of Marine Drugs, Ocean University of China, Qingdao 266003, China.
Li
Ying-xia
YX
Sun
Xue
X
Qu
Feng
F
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000627:therapeutic use; D007052:Ibuprofen / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000627:therapeutic use; D007249:Inflammation / Q000188:drug therapy; D008297:Male; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D011897:Random Allocation
D000894:Anti-Inflammatory Agents, Non-Steroidal; D007052:Ibuprofen