7α,15α-Ethano bridged steroids. Synthesis and progesterone receptor interaction

The synthesis of 7α,15α-ethano bridged steroids is described. Diels-Alder reaction of 3-methoxyestra-1,3,5(10),7,14-pentaen-17-one 4 with ethylene under high pressure provides efficient synthetic access to this class of steroids. Compounds 15 and 17 were tested for their binding affinities to the pr...

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Published inTetrahedron Vol. 55; no. 37; pp. 11267 - 11274
Main Authors Egner, Ursula, Fritzemeier, Karl-Heinrich, Halfbrodt, Wolfgang, Heinrich, Nikolaus, Kuhnke, Joachim, Müller-Fahrnow, Anke, Neef, Günter, Schöllkopf, Klaus, Schwede, Wolfgang
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.09.1999
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Summary:The synthesis of 7α,15α-ethano bridged steroids is described. Diels-Alder reaction of 3-methoxyestra-1,3,5(10),7,14-pentaen-17-one 4 with ethylene under high pressure provides efficient synthetic access to this class of steroids. Compounds 15 and 17 were tested for their binding affinities to the progesterone receptor (PR). Two low energy conformations 17a and 17b could be identified by force field calculations of compound 17. Both conformations were analysed in complex with the ligand binding domain of the human progesterone receptor (hPR LBD). The synthesis of 7α,15α-ethano bridged steroids is described. Key step in the synthetic approach is a Diels-Alder reaction of diene 4 with ethylene under high pressure. The new compounds were tested for their binding affinities to the progesterone receptor (PR).
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00638-9