Synthesis and preliminary anti-inflammatory evaluation of 17beta-amino-3beta-methoxy-5-androstene hydrochloride and related derivatives

To study the anti-inflammatory properties of 17beta-amino-steroids, some 17beta-aminoandrostene hydrochlorides based on the 3beta-methoxy-5-androstene nucleus were prepared. The syntheses were accomplished via a two-stage amination of 3beta-methoxy-5-androsten-17-one, involving reduction of an intermediate 17-imine or, for the synthesis of 17beta-amino-3beta-methoxy-5-androstene, the 17-oxime. The compounds were examined for anti-inflammatory activity in the rat cotton pellet model of inflammation. All tested aminosteroids displayed significant activity. Two compounds also were screened in an adjuvant-induced arthritis model of inflammation and displayed activity.