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 in | Tetrahedron Vol. 55; no. 37; pp. 11267 - 11274 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Elsevier Ltd
01.09.1999
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Online Access | Get full text |
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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). |
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/S0040-4020(99)00638-9 |