Klaus Schöllkopf

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

Abstract 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).

Synthesis and Biological Activity of 11,19-Bridged Progestins

A synthetic approach to 11,19-bridged progestins is described. The key step in the synthesis is a 6-endo-trig radical cyclisation. The new progestins were tested for their biological activities in vitro and in vivo and compared to those of known progestins.