Abstract

FRYE, Stephen. Photochemical Rearrangement of a 6-Azasteroid Oxaziridine to a Novel 17β-Carbomethoxy-A-homo-B-seco-6-aza-3, 5-androstanedione. J. Mex. Chem. Soc [online]. 2009, vol.53, n.3, pp.131-133. ISSN 1870-249X.

4- and 6-azasteroids have been shown to be potent inhibitors of human 5α,-reductase and certain azasteroids have shown significant clinical benefit in the treatment of androgen-related disorders. In an effort to expand the diversity of steroidal heterocycles synthetically accessible for structure-activity relationship exploration, a novel reaction sequence was applied to the preparation of the 6-aza-steroid framework. To this end, photolysis of the oxaziridine derived from 17β-carbomethoxy-3β-triisopropylsilyloxy-6-azaandrost-5-ene (1) yielded a novel 7, 5-steroidal ring system that was evaluated for inhibition of human type 1 and 2 5α-reductase.

Keywords : Azasteroids; 5α-reductase; steroidal heterocycles; photochemistry; synthesis; oxaziridine.

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