Issue 22, 2001

Putative metabolites of fulvestrant, an estrogen receptor downregulator. Improved glucuronidation using trichloroacetimidates

Abstract

Following regioselective protection of the estrogen receptor downregulator fulvestrant (ICI 182,780) 1 as its 17-acetate 2 or 3-benzoate 4, the 3-sulfate 5 and 3- and 17-glucuronide conjugates 8 and 12 were prepared. Satisfactory preparation of 12 required use of the tri-O-isobutyryl imidate derivative 10 in conjunction with an inverse-addition technique not previously employed in glucuronidation. The value of this method for simpler aglycones is discussed together with a study of variations in donor acyl substituent and catalyst. Another putative metabolite, the 17-ketone 19, was prepared by direct oxidation of 1.

Graphical abstract: Putative metabolites of fulvestrant, an estrogen receptor downregulator. Improved glucuronidation using trichloroacetimidates

Article information

Article type
Paper
Submitted
20 Jun 2001
Accepted
12 Oct 2001
First published
02 Nov 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 3037-3041

Putative metabolites of fulvestrant, an estrogen receptor downregulator. Improved glucuronidation using trichloroacetimidates

J. R. Ferguson, J. R. Harding, D. A. Killick, K. W. Lumbard, F. Scheinmann and A. V. Stachulski, J. Chem. Soc., Perkin Trans. 1, 2001, 3037 DOI: 10.1039/B105397N

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