Cardenolide analogs. 2. 22-Methylenecard-14-enolides
- 1 June 1977
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 20 (6), 841-844
- https://doi.org/10.1021/jm00216a022
Abstract
22-Methylene-3.beta.-hydroxy-5.beta.,20(S)-card-14-enolide and 22-methylene-3.beta.-hydroxy-5.beta.,20(R)-card-14-enolide were synthesized from digitoxin [an important drug used for treating congestive heart failure]. Attempts to prepare the 14.beta.-hydroxy-22-methylene analogues were unsuccessful. The 20(R) isomer was twice as active as 14-dehydrodigitoxigenin (17) in Na+, K+-ATPase [rat brain] inhibition studies. The 20(S) isomer was significantly less active than 17. The hydrolysis of steroid 3.beta.-tert-butyldimethylsilyl ethers was also much more difficult than with nonsteroids.This publication has 3 references indexed in Scilit:
- Cardenolide analogs. 1. A 17.beta.-unsaturated aldehydeJournal of Medicinal Chemistry, 1976
- Structures of modified cardenolides. II. (20R)-3β-Hydroxy-22-methylene-5β-card-14-enolineActa crystallographica Section B, Structural science, crystal engineering and materials, 1976
- ON THE ACTION OF STROPHANTHIN GCanadian Journal of Biochemistry, 1965