[Synthesis of chlormadinol acetate-3-beta-O-alpha-1-arabinofuranosides with positive inotropic action].
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.
Schwabe
K
K
Zentralinstitut für Krebsforschung, Akademie der Wissenschaften der DDR, Bereich Experimentalle und Klinische Chemotherapie, Berlin-Buch.
D000818:Animals; D001089:Arabinose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D002316:Cardiotonic Agents / Q000138:chemical synthesis*; D002415:Cats; D055598:Chemical Phenomena; D002621:Chemistry; D002715:Chlormadinone Acetate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D009200:Myocardial Contraction / Q000187:drug effects
D002316:Cardiotonic Agents; D002715:Chlormadinone Acetate; C065233:chlormadinol acetate-3-O-alpha-arabinofuranoside; D001089:Arabinose
Synthese des Chlormadinolacetat-3 beta-O-alpha-L-arabinofuranosids mit positiv inotroper Wirkung.