Synthesis and biological testing of 4'-(dimethylamino)-17 beta-hydroxy-17 alpha-(1-propynyl)benzo[12,12a]-11 alpha,18-cyclo-12a,12b-dihomo-13 alpha-estr-4-en-3-one: an interesting RU 38 486 analog.

Abstract:

:A partial synthesis of the title compound, 4'-(dimethylamino)-17 beta-hydroxy-17 alpha-(1-propynyl)benzo[12,12a]-11 alpha,18-cyclo-12a,12b- dihomo-13 alpha-estr-4-en-3-one 1, is reported. The key step in this synthesis represents an intramolecular alkenylaryl radical cyclization. Treatment of 18-[bromo-5-(dimethylamino)phenyl]gona-5,9(11)-diene-3,17-dione-3, 17- bis[cyclic 1,2-ethanediyl acetal] 5 with tributyl tin hydride and a radical initiator introduces the desired 11 beta,18-bridge. The reduced progesterone receptor affinity of this RU 38 486 analog contributes valuable information to the empirical characterization of the steroid binding site of the receptor protein and explains the observed lack of in vivo antigestational activity.

journal_name

Steroids

journal_title

Steroids

authors

Ottow E,Beier S,Elger W,Fritzemeier KH,Neef G,Wiechert R

doi

10.1016/0039-128x(94)90026-4

subject

Has Abstract

pub_date

1994-03-01 00:00:00

pages

185-9

issue

3

eissn

0039-128X

issn

1878-5867

pii

0039-128X(94)90026-4

journal_volume

59

pub_type

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