PMID: 9185294Jun 1, 1997Paper

Synthesis of novel 21-trifluoropregnane steroids: inhibitors of 17 alpha-hydroxylase/17,20-lyase (17 alpha-lyase)

Steroids
Vincent C O NjarA M Brodie

Abstract

Novel 21-trifluoropregnenolone (6), 21-trifluoroprogesterone (7) and related compounds 4a and 8 have been synthesized in high yields from 3 beta-acetoxyandrost-5-ene-17 beta-carbaldehyde (3). The key reaction was the conversion of 3 into the 21-trifluoromethyl-20-alcohol as a diastereomeric mixture (4) by trifluoromethyltrimethylsilane (TMS-CF3) in the presence of tetrabutylammonium fluoride (TBAF). All compounds, including 6 and 7, were unambiguously characterized by IR, 1H and 19F NMR, high-resolution mass spectrometry (HRMS), and elemental analysis. On this basis, we concluded that the only report of an earlier synthesis of 6 and 7 is erroneous. Enzyme inhibition studies showed that 20 xi-hydroxy-21-trifluoropregn-4-en-3-one (8) is a potent inhibitor (IC50 value = 0.6 microM) of rat 17 alpha-hydroxylase/17,20-lyase.

References

May 14, 1976·The Journal of Organic Chemistry·M L Raggio, D S Watt
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Citations

Apr 15, 2004·Bioorganic & Medicinal Chemistry·Nobuyuki MatsunagaAkihiro Tasaka
May 28, 2003·The Journal of Steroid Biochemistry and Molecular Biology·I DucR Delansorne
Feb 5, 2000·The Journal of Steroid Biochemistry and Molecular Biology·I P NnaneA M Brodie
Feb 12, 2002·Bioorganic & Medicinal Chemistry·Joseph P BurkhartNorton P Peet
Oct 18, 2011·The Journal of Steroid Biochemistry and Molecular Biology·Francis K YoshimotoRichard J Auchus

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