7 alpha,15 alpha-ethano bridged steroids. Synthesis and progesterone receptor interaction

Authors
Egner, U Fritzemeier, KH Halfbrodt, W Heinrich, N Kuhnke, J Muiller-Fahrnow, A Neef, G Schollkopf, K Schwede, W
Citation
U. Egner et al., 7 alpha,15 alpha-ethano bridged steroids. Synthesis and progesterone receptor interaction, TETRAHEDRON, 55(37), 1999, pp. 11267-11274
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
37
Year of publication
1999
Pages
11267 - 11274
Database
ISI
SICI code
0040-4020(19990910)55:37<11267:7AABSS>2.0.ZU;2-O
Abstract
The synthesis of 7 alpha,15 alpha-ethano bridged steroids is described. Die ls-Alder reaction of 3-methoxyestra-1,3,5(10),7,14-pentaen-17-one 4 with et hylene under high pressure provides efficient synthetic access to this clas s of steroids. Compounds 15 and 17 were tested for their binding affinities to the progesterone receptor (PR). Two low energy conformations 17a and 17 b could be identified by force field calculations of compound 17. Both conf ormations were analysed in complex with the ligand binding domain of the hu man progesterone receptor (hPR LBD). (C) 1999 Elsevier Science Ltd. All rig hts reserved.