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

doi:10.1021/jm00216a022

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 journal › Article › peer-review

5 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 language	English (US)
Pages (from-to)	841-844
Number of pages	4
Journal	Journal of medicinal chemistry
Volume	20
Issue number	6
DOIs	https://doi.org/10.1021/jm00216a022
State	Published - Jun 1 1977

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@article{ce2246fad68b4d2baa88050e26812be9,

title = "Cardenolide Analogs. 2. 22-Methylenecard-14-Enolides",

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.",

author = "Fullerton, \{Dwight S.\} and Gilman, \{Thomas M.\} and Pankaskie, \{Marvin C.\} and Khalil Ahmed and From, \{Arthur H.L.\} and Duax, \{William L.\} and Rohrer, \{Douglas C.\}",

year = "1977",

month = jun,

day = "1",

doi = "10.1021/jm00216a022",

language = "English (US)",

volume = "20",

pages = "841--844",

journal = "Journal of medicinal chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "6",

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TY - JOUR

T1 - Cardenolide Analogs. 2. 22-Methylenecard-14-Enolides

AU - Fullerton, Dwight S.

AU - Gilman, Thomas M.

AU - Pankaskie, Marvin C.

AU - Ahmed, Khalil

AU - From, Arthur H.L.

AU - Duax, William L.

AU - Rohrer, Douglas C.

PY - 1977/6/1

Y1 - 1977/6/1

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0017411419

UR - https://www.scopus.com/pages/publications/0017411419#tab=citedBy

U2 - 10.1021/jm00216a022

DO - 10.1021/jm00216a022

M3 - Article

C2 - 141522

AN - SCOPUS:0017411419

SN - 0022-2623

VL - 20

SP - 841

EP - 844

JO - Journal of medicinal chemistry

JF - Journal of medicinal chemistry

IS - 6

ER -

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

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