AIM: (+/-) 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. CONCLUSION: It was found that 12a showed better anti-inflammatory activity than (+/-) ibuprofen.
AIM: (+/-) 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. CONCLUSION: It was found that 12a showed better anti-inflammatory activity than (+/-) ibuprofen.