Synthesis of 11.beta.,13.beta.- and 13.beta.,16.beta.-propano steroids: probes of hormonal activity
- 1 August 1979
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 22 (8) , 966-970
- https://doi.org/10.1021/jm00194a016
Abstract
Syntheses of 11.beta.,13.beta.- and 13.beta.,16.beta.-propano derivatives of 17.alpha.-ethynyl-17.beta.-hydroxygon-4-en-3-one are described. The 13.beta.,16.beta. bridge was constructed by intramolecular alkylation of the C-16 enolate anion from 3-methoxy-13.beta.-[3''-(tosyloxy)propyl]gona-3,5-dien-17-one, the latter being obtained via Birch reduction of both aryl groups of 17.beta.-hydroxy-3-methoxy-13.beta.-(3''-phenoxypropyl)gona-1,3,5(10),8-tetraene (1). The 11.beta.,13.beta. bridge was constructed by Prins cyclization of 17.beta.-acetoxy-3-methoxy-13.beta.-(3''-oxopropyl)gona-1,3,5(10),9(11)-tetraene, itself obtained via Birch reduction of only the side-chain aryl group of 1. Binding affinities of certain of these compounds and substituted 13.beta.-propyl derivatives of 17.alpha.-ethynyl-17.beta.-hydroxygon-4-en-3-one for the [mouse, rat] uterine cytosol receptor of progesterone are reported, and the origin of the high progestational activity of norgestrel and 11.beta.-substituted progestins is discussed.This publication has 1 reference indexed in Scilit:
- Synthesis, antifertility activity, and protein binding affinity of 7(8 .fwdarw. 11.alpha.)abeo steroidsJournal of Medicinal Chemistry, 1977