Synthesis of chlormadinol acetate-3-beta-O-alpha-1-arabinofuranosides with positive inotropic action
Schwabe, K.
Die Pharmazie 45(4): 250-251
1990
ISSN/ISBN: 0031-7144 PMID: 1696385 Document Number: 355363
The synthesis of chlormadinol acetate-3 beta-O-alpha-L-arabinofuranoside (3; 17 alpha-Acetoxy-6-chloro-pregna-4,6-diene-20-one-3 beta-O-alpha-L- arabinofuranoside) is described. Glycosidation of chlormadinol acetate (1) was accomplished with excess 2,3,5-tri-O-benzyl-alpha-L-arabinofuranosyl chloride, Fétizon reagent, mercury cyanide and bromide in toluene at room temperature. Debenzoylation into compound 3 was carried out with methanol/methylen chloride saturated with ammonia at low temperature. Surprisingly, substance 3 shows positive inotropic effects on cats in vivo, whereas the aglycone 1 produces negative inotropy.