Cardiac glycoside-like structure and function of 5 beta,14 beta-pregnanes.


5 beta-Reduction and 14 beta-substitution convert the planar progesterone molecule to the cardiac glycoside configuration--A and D rings of the steroid moiety are bent toward the alpha-face relative to the B and C rings. Potency of the 5 beta,14 beta-derivative in a [3H]ouabain binding assay or its ability to inhibit the sodium pump in red blood cells is enhanced by 3 beta-hydroxylation, 20 beta-hydroxylation, and 3 beta-glycosidation. Synthesis of 14,20 beta-dihydroxy-3 beta-(beta-D-glucopyranosyloxy)- 5 beta,14 beta-pregnane from digitoxin is described. The glucoside is 1/20 as potent as ouabain and elicits prominent, sustained, positive inotropy in isolated cardiac muscle.

Cite this paper

@article{Templeton1989CardiacGS, title={Cardiac glycoside-like structure and function of 5 beta,14 beta-pregnanes.}, author={John F. Templeton and Vipul Kumar and Deepak Bose and Frank S. Labella}, journal={Journal of medicinal chemistry}, year={1989}, volume={32 8}, pages={1977-81} }