Rayat, Harnak Singh (1995) The synthesis of potential steroid receptor antagonists. PhD thesis, University of Warwick.

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Abstract

The first section of this thesis presents a review of the literature on
endocrine hormones, synthetic steroids, and synthetic steroid receptor
antagonists. Particular emphasis is placed upon the estrogen, progesterone
and glucocorticoid activity of these compounds. The structure, activity and
preparation of some progesterone/glucocorticoid receptor antagonists is
also reviewed.
The second section of this thesis presents a route for the synthesis of
19-aryl substituted androstanes. These compounds have been designed to
explore their potential antiprogestational and antiglucocorticoid activity. It
is demonstrated that a bulky aromatic functionality may be introduced at
the sterically hindered C-19 methyl group, by the nucleophilic attack of an
organometallic nucleophile on a 10~-formyl-19-norandrostane, which is
suitably protected at positions C-3 and C-17. The subsequent careful
manipulation of the C-3 and C-17 functionalities has led to a succesful 11
step synthesis (scheme 4.19) of 17~-hydroxy-17a-(prop-l-yne)-19-(p-N,N-
dimethylaminophenyl)androst-5-en-3-one (3.1), which should be of interest
for biological evaluation.

Item Type:	Thesis (PhD)
Subjects:	Q Science > QD Chemistry
Library of Congress Subject Headings (LCSH):	Steroids, Endocrinology, Hormones, Estrogen -- Antagonists, Estrogen -- Receptors, Progesterone -- Antagonists, Progesterone -- Receptors
Official Date:	March 1995
Dates:	Date Event March 1995 Submitted
Institution:	University of Warwick
Theses Department:	Department of Chemistry
Thesis Type:	PhD
Publication Status:	Unpublished
Supervisor(s)/Advisor:	Matlin, S. A.
Extent:	vi, 184 leaves : illustrations
Language:	eng

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