Photochemical rearrangement of a 6-azasteroid oxaziridine to a novel 17b-carbomethoxy-a-homo-b-seco-6-aza-3, 5-androstanedione Reportar como inadecuado




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Journal of the Mexican Chemical Society 2009, 53 (3)

Autor: Stephen Frye

Fuente: http://www.redalyc.org/


Introducción



Journal of the Mexican Chemical Society ISSN: 1870-249X editor.jmcs@gmail.com Sociedad Química de México México Frye, Stephen Photochemical Rearrangement of a 6-Azasteroid Oxaziridine to a Novel 17B-Carbomethoxy-A-homoB-seco-6-aza-3, 5-androstanedione Journal of the Mexican Chemical Society, vol.
53, núm.
3, julio-septiembre, 2009, pp.
131-133 Sociedad Química de México Distrito Federal, México Available in: http:--www.redalyc.org-articulo.oa?id=47512154008 How to cite Complete issue More information about this article Journals homepage in redalyc.org Scientific Information System Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Non-profit academic project, developed under the open access initiative J.
Mex.
Chem.
Soc.
2009, 53(3), 131-133 © 2009, Sociedad Química de México ISSN 1870-249X Article Photochemical Rearrangement of a 6-Azasteroid Oxaziridine to a Novel 17β-Carbomethoxy-A-homo-B-seco-6-aza-3, 5-androstanedione Stephen Frye*1 Department of Medicinal Chemistry, Glaxo Inc.
Research Institute, Five Moore Drive, Research Triangle Park, North Carolina Received June 23, 2009; accepted August 31, 2009 Abstract.
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-azasteroid 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. Key words: Azasteroids, 5a-reductase, steroidal heterocycles, photochemistry, synthesis, oxaziridine Resumen.
Los 4- y 6-azaesteroides mostraron ser potent...





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