188976-60-5Relevant academic research and scientific papers
Synthesis and structure-activity relationships of 17β-substituted 14β- hydroxysteroid 3-(α-l-rhamnopyranoside)s: Steroids that bind to the digitalis receptor
Templeton, John F.,Ling, Yangzhi,Marat, Kirk,LaBella, Frank S.
, p. 1439 - 1446 (2007/10/03)
The preparation of 17β-substituted 14β-hydroxysteroid C-3 α-L- rhamnopyranosides is described. These derivatives have a 14β,20-ether, 14β,20-lactone, or 17β-CH2CH2OH, -CH2CH2NH2, -CH=CHNO2(
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
Templeton,Ling,Zeglam,LaBella
, p. 42 - 45 (2007/10/02)
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.
