Synthesis of (±) ibuprofen sugar derivatives

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-β-D-galactopyranose, 1,3,4,5-tetra-O-acetyl-2-deoxy-2-amino-β-D-gluctopyranose, 3,4,6-tri-O-acetyl-2-deoxy-2-n-acetyl-β-D-gluctosylamine and 2,3,6,2′,3′,4′,6′-hepta-O-acetyl-β-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.