Studies on modified estrogens: Towards the synthesis of novel 14,15-cyclopropa[a]estra-1,3,5(10),8-tetraenes

Authors
Schwarz, S Thieme, I Kosemund, D Undeutsch, B Kummer, M Gorls, H Romer, W Kaufmann, G Elger, W Hillisch, A Schneider, B
Citation
S. Schwarz et al., Studies on modified estrogens: Towards the synthesis of novel 14,15-cyclopropa[a]estra-1,3,5(10),8-tetraenes, PHARMAZIE, 56(11), 2001, pp. 843-849
Citations number
18
Categorie Soggetti
Pharmacology & Toxicology
Journal title
PHARMAZIE
ISSN journal
00317144 → ACNP
Volume
56
Issue
11
Year of publication
2001
Pages
843 - 849
Database
ISI
SICI code
0031-7144(200111)56:11<843:SOMETT>2.0.ZU;2-L
Abstract
To improve the ratio of non-hormonal to hormonal activity, estrogens 3 and 4 were modified at various molecule positions. Isomerization of the 14 alph a ,15 zeta -methylene bridge, controlled 3-methoxy group cleavage with resp ect to the 14 alpha ,15 alpha -methylene bridge stereochemistry, reduction of the 8-double bond, and substitution of the oxyfunctionality at C-17 by a methylene and a difluoromethylene moiety were in the focus. As a result of in vivo and in vitro tests, compounds 27 and 29 were selected as potential follow-up candidates of lead 3.