Synthesis of antioxidative and anti-inflammatory drugs glucoconjugates.
Glucoconjugates of (+/-)-ibuprofen, (+/-)-alpha-tocopherol (vitamin E), gentisic acid, gallic acid, 2,6-bis(tert-butyl)-4-thiophenol, and N-acetyl-L-cysteine were prepared with the objective of increasing the bioavailability of such antioxidant and anti-inflammatory drugs. The O-glucosides were synthesized using benzylated alpha-D-glucopyranosyl trichloracetimidate as glycosyl donor. For the synthesis of the S-glucosides, the glycosyl donor 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose provided higher yields than the corresponding O-acetylated imidate.
Uhrig
R K
RK
Zentrum für Molekularbiologie Heidelberg (ZMBH), Germany. r.uhrig@dkfz-heidelberg.de
Picard
M A
MA
Beyreuther
K
K
Wiessler
M
M
D000111:Acetylcysteine / Q000031:analogs & derivatives; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis*; D000975:Antioxidants / Q000138:chemical synthesis*; D001682:Biological Availability; D005707:Gallic Acid / Q000031:analogs & derivatives; D005841:Gentisates; D005960:Glucosides / Q000138:chemical synthesis; D006001:Glycoconjugates / Q000138:chemical synthesis*; D062385:Hydroxybenzoates / Q000737:chemistry; D007052:Ibuprofen / Q000031:analogs & derivatives; D009682:Magnetic Resonance Spectroscopy; D010636:Phenols / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry; D014810:Vitamin E / Q000031:analogs & derivatives
D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D005841:Gentisates; D005960:Glucosides; D006001:Glycoconjugates; D062385:Hydroxybenzoates; D010636:Phenols; D013438:Sulfhydryl Compounds; D014810:Vitamin E; D005707:Gallic Acid; C042983:thiophenol; C010925:2,5-dihydroxybenzoic acid; D007052:Ibuprofen; D000111:Acetylcysteine