Cardenolide Analogs. 2. 22-Methylenecard-14-Enolides

Dwight S. Fullerton, Thomas M. Gilman, Marvin C. Pankaskie, Khalil Ahmed, Arthur H.L. From, William L. Duax, Douglas C. Rohrer

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

22-Methylene-3β-hydroxy-5β,20(S)-card-14-enolide (11) and 22-methylene-3β-hydroxy-5β,20(fi)-card-14-enolide (12) were synthesized from digitoxin (1). Attempts to prepare the 14β-hydroxy-22-methylene analogues were unsuccessful. The 20(R) isomer (12) was found in Na+,K+-ATPase inhibition studies to be twice as active as 14-dehydrodigitoxigenin (17). The 20(S) isomer (11) was significantly less active than 17. The hydrolysis of steroid 3β-tert-butyldimethylsilyl ethers was also found to be much more difficult than with nonsteroids.

Original languageEnglish (US)
Pages (from-to)841-844
Number of pages4
JournalJournal of medicinal chemistry
Volume20
Issue number6
DOIs
StatePublished - Jun 1 1977

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