1235-97-8Relevant articles and documents
Microbial transformation of 17α-ethynyl- and 17α-ethylsteroids, and tyrosinase inhibitory activity of transformed products
Choudhary, M. Iqbal,Sultan, Sadia,Khan, Mahmud Tareq Hassan,Rahman, Atta-ur
, p. 798 - 802 (2005)
The microbial transformation of the 17α-ethynyl-17β- hydroxyandrost-4-en-3-one (1) (ethisterone) and 17α-ethyl-17β- hydroxyandrost-4-en-3-one (2) by the fungi Cephalosporium aphidicola and Cunninghamella elegans were investigated. Incubation of compound 1 with C. aphidicola afforded oxidized derivative, 17α-ethynyl-17β- hydroxyandrosta-1,4-dien-3-one (3), while with C. elegans afforded a new hydroxy derivative, 17α-ethynyl-11α,17β-dihydroxyandrost-4-en-3-one (4). On the other hand, the incubation of compound 2 with the fungus C. aphidicola afforded 17α-ethyl-17β-hydroxyandrosta-1,4-dien-3-one (5). Two new hydroxylated derivatives, 17α-ethyl-11α,17β- dihydroxyandrost-4-en-3-one (6) and 17α-ethyl-6α,17β-dihydroxy- 5α-androstan-3-one (7) were obtained from the incubation of compound 2 with C. elegans. Compounds 1-6 exhibited tyrosinase inhibitory activity, with compound 6 being the most potent member (IC50 = 1.72 μM).
STEROID SPIROLACTONIZATION
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Page 138, (2008/06/13)
A steroid comprising a 17-spirolactone or corresponding open lactone structure is obtained by carbonylation of a 17-alkenyl or 17-alkynyl substrate. A 17-alkenyl intermediate may be prepared by semi-hydrogenation of a 17-alkynyl group. Multiple reaction schemes are disclosed for preparation of a 3-keto-9,11-epoxy-17-spirolactone steroid such as eplerenone. Novel intermediates are also disclosed, as well as steps for forming such novel intermediates, or converting them to further intermediates or products, by semi-hydrogenation, carbonylation, 6,7-dehydrogenation, furylation or other transformations or combinations thereof.
