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On cardioactive steroids. Communication XV. A stereoselective synthesis of (21 R )‐21‐methyldigitoxigenin, a fully active cardenolide with a wide margin of safety: A contribution to the topology of the Digitalis receptors
Author(s) -
Wiesner Karel,
Tsai Thomas Y. R.,
Kumar Ravindra,
Sivaramakrishnan Harihran
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670427
Subject(s) - digitoxigenin , chemistry , epimer , cardenolide , inotrope , stereochemistry , stereoselectivity , topology (electrical circuits) , biochemistry , endocrinology , glycoside , combinatorics , mathematics , catalysis , medicine
Two efficient preparations of the title compound, one from common C 19 ‐steroids, the other frm digitoxigenin, are described. The less active minor epimer (21 S )‐methyldigitoxigenin was also obtained and characterized. The positive inotropic effects and margins of safety of the two C(21)‐epimers (tested as glucosides) are discussed in terms of the topological properties of the Digitalis receptors.