Apparent bioisosteric replacement of -S- by NCN: synthesis of N-cyano-2-aza-A-nor-5.alpha.-androstan-17.beta.-ol acetate, an aza steroid androgen
- 1 January 1979
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 22 (1) , 119-120
- https://doi.org/10.1021/jm00187a028
Abstract
The synthesis of N-cyano-2-aza-A-nor-5.alpha.-androstan-17.beta.-ol acetate is described. Cyclization of 1,4-dibromo-1,4-seco-2,3-bisnor-5.alpha.-androstan-17.beta.-ol acetate with benzylamine in the presence of KI 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 1st hormonally active steroid [in rats] containing nitrogen as a heteroatom in the perhydrocyclopentanophenanthrene nucleus.This publication has 0 references indexed in Scilit: