261506-31-4Relevant articles and documents
Putative metabolites of fulvestrant, an estrogen receptor downregulator. Improved glucuronidation using trichloroacetimidates
Ferguson,Harding,Killick,Lumbard,Scheinmann,Stachulski
, p. 3037 - 3041 (2007/10/03)
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.
Glucuronide and sulfate conjugates of ICI 182,780, a pure anti- estrogenic steroid. Order of addition, catalysis and substitution effects in glucuronidation
Ferguson, John R.,Harding, John R.,Lumbard, Keith W.,Scheinmann, Feodor,Stachulski, Andrew V.
, p. 389 - 392 (2007/10/03)
The 3-sulfate 4 and 3- and 17-glucuronide conjugates 5 and 6 of the pure anti-estrogenic steroid ICI 182,780 1, which is expected to be an effective agent for the treatment of breast cancer, have been prepared. The synthesis of 6 could only be satisfactorily achieved using an inverse addition technique, not previously employed in the glucuronic acid series: the value of this technique for some other aglycones is discussed.
