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J Nat Prod. 2013 Oct 25;76(10):1966-9. doi: 10.1021/np400585t. Epub 2013 Sep 27.

Synthesis and bioconversions of formestane.

Author information

1
Chemistry, Biochemistry and Physics Department, The University of Tampa , 401 West Kennedy Boulevard, Tampa, Florida 33606-1490, United States.

Abstract

In an effort to generate new steroidal aromatase inhibitors, formestane (4-hydroxyandrost-4-ene-3,17-dione) (1) was biotransformed by Rhizopus oryzae to yield the known 4β,5α-dihydroxyandrostane-3,17-dione as the major product (5) and bioconverted by Beauveria bassiana to afford the known reduced 4,17β-dihydroxyandrost-4-en-3-one (6) and 3α,17β-dihydroxy-5β-androstan-4-one (7) and the new 4,11α,17β-trihydroxyandrost-4-en-3-one (8). All the metabolites showed more potent activities than their parent congener in the aromatase and MCF-7 breast cancer assays. The bioactivities and structural elucidation of these metabolites as well as the semisynthesis of formestane (1) from testosterone (2) are reported herein.

PMID:
24074257
DOI:
10.1021/np400585t
[Indexed for MEDLINE]

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