302965-12-4Relevant articles and documents
Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners
Crooks, Peter A.,Kottayil, Santosh G.,Al-Ghananeem, Abeer M.,Byrn, Stephen R.,Allan Butterfield
, p. 4291 - 4295 (2006)
A series of 3-O-acyl-6-O-sulfate esters of morphine, dihydromorphine, N-methylmorphinium iodide, codeine, and dihydrocodeine were prepared and evaluated for their ability to bind to μ-, δ-, κ1-, κ2-, and κ3-opiate receptors. Several compounds exhibited good affinity for the μ-opiate receptor. Morphine-3-O-propionyl-6-O-sulfate had four times greater affinity than morphine at the μ-opiate receptor and was the most selective compound at this receptor subtype.
6-O-Glycosylation of morphine derivatives using thioglycosides as glycosyl donors
Rukhman,Yudovich,Nisnevich,Gutman
, p. 1241 - 1246 (2007/10/03)
A novel approach was developed for the synthesis of the pharmaceutically important morphine and dihydromorphine 6-β-D-glucuronides. The key step involves a selective 6-O-glycosylation of 3-O-protected morphines and dihydromorphines with thioglycosides that serve as glycosyl donors in the presence of thiophilic promoters. This novel approach may be useful for the O-glycosylation of other alkoloid derivatives.
