Apparent bioisosteric replacement of--S--by NCN: synthesis of N--cyano-2-aza-A-nor-5alpha-androstan-17beta-ol acetate, an aza steroid androgen.
The synthesis of N-cyano-2-aza-A-nor-5alpha-androstan-17beta-ol acetate is described. Cyclization of 1,4-dibromo-1,4-seco-2,3bisnor-5alpha-androstan-17beta-ol acetate with benzylamine in the presence of potassium iodide gives the N-benzyl-2-aza-A-nor steroid. Debenzylation with cyanogen bromide (Von Braun reaction) affords the N-cyano-2-aza-A-nor steroid, which has androgenic activity slightly weaker than that of the corresponding thia compound. The results indicate that NCN may be substituted for--S--as well as for =S. This compound is the first hormonally active steroid containing nitrogen as a heteroatom in the perhydrocyclopentanophenanthrene nucleus.
D000731:Androstanes / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D001378:Azasteroids / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D009132:Muscles / Q000187:drug effects; D009929:Organ Size / Q000187:drug effects; D051381:Rats; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D045165:Testosterone Congeners / Q000138:chemical synthesis*
D000731:Androstanes; D001378:Azasteroids; D013260:Steroids, Heterocyclic; D045165:Testosterone Congeners