Fluoro-clomiphene and its synthetic precursors: synthesis and receptor binding.

Abstract:

:In an attempt to synthesize compounds with selective estrogen-receptor binding, fluoro- and amino-clomiphene were totally synthesized from benzyl chloride, and their estrogenic/antiestrogenic activity as well as that of some of their chemical intermediates was evaluated. The triazene prepared from the amino-clomiphene was converted into fluoro-clomiphene with 39% yield. In the uterotropic test, both amino- and fluoro-clomiphene exerted mild equipotent estrogenic activity, with minimal saturation doses being 50 and 100 micrograms/rat/day for three days. In the receptor binding test both derivatives demonstrated similar displacement, with an A50% value in the 10(-5) M range, as compared to 10(-6) M for clomiphene and 10(-9) M for diethyl-stilbestrol. This synthesis may be useful for the preparation of 18F-labeled clomiphene for biodistribution studies.

journal_name

Steroids

journal_title

Steroids

authors

Gazit A,Livshitz T,Shani J

doi

10.1016/0039-128x(86)90042-5

subject

Has Abstract

pub_date

1986-07-01 00:00:00

pages

73-84

issue

1-2

eissn

0039-128X

issn

1878-5867

pii

0039-128X(86)90042-5

journal_volume

48

pub_type

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