- Synthesis of 20-hydroxy-, 20-amino-, and 20-nitro-14-hydroxy-21-nor- 5β,14β-pregnane C-3 glycosides and related derivatives: Structure-activity relationships of pregnanes that bind to the digitalis receptor
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The preparation of derivatives of 14-hydroxy-21-nor-5β,14β-pregnane and 5β,14β-pregnane C-3 α-L-rhamnosides and tris-β-D-digitoxosides is described. These derivatives, possessing a C-17β COCH2OH, CH2OH, CO2H, CO2Me, CH2NH2, or CH2NO2 group, bind to the digitalis receptor recognition site of heart muscle as measured in a radioligand binding assay. The 21-norpregnane derivatives consistently show greater binding affinity than the corresponding 20α- and 20β-pregnane analogs. The C-20 nitro rhamnoside is comparable to digitoxin in binding affinity. The 17β-CH2NO2 group is the most effective replacement for the unsaturated lactone in the binding assay found so far, showing binding affinity comparable to that of the cardiac glycosides.
- Templeton,Ling,Zeglam,LaBella
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