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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
3
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pubmed:dateCreated |
1990-4-6
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pubmed:abstractText |
A series of unsaturated steroids bearing a 3-carboxy substituent has been prepared and assayed in vitro as inhibitors of human and rat prostatic steroid 5 alpha-reductase (EC 1.3.1.30). It is proposed that the observed tight binding of the 3-androstene-3-carboxylic acids is due to mimicry of a putative, high-energy, enzyme-bound enolate intermediate formed during the NADPH-dependent conjugate reduction of testosterone by steroid 5 alpha-reductase. These compounds were prepared through palladium(0)-catalyzed carbomethoxylations of enol (trifluoromethyl)sulfonates derived from 3-keto precursors. Modification of A and B ring unsaturation and substitution at C-3, -4, -6, and -11 was explored. Mono- and dialkylcarboxamides were employed as 17 beta side chains to enhance inhibitory activity with the human enzyme.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Mar
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
33
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
943-50
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pubmed:dateRevised |
2010-11-18
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pubmed:meshHeading |
pubmed-meshheading:2308145-5-alpha Reductase Inhibitors,
pubmed-meshheading:2308145-Animals,
pubmed-meshheading:2308145-Carboxylic Acids,
pubmed-meshheading:2308145-Humans,
pubmed-meshheading:2308145-Male,
pubmed-meshheading:2308145-Prostate,
pubmed-meshheading:2308145-Rats,
pubmed-meshheading:2308145-Steroids,
pubmed-meshheading:2308145-Structure-Activity Relationship
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pubmed:year |
1990
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pubmed:articleTitle |
Inhibition of steroid 5 alpha-reductase by unsaturated 3-carboxysteroids.
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pubmed:affiliation |
Department of Medicinal Chemistry, Smith Kline & French Laboratories, King of Prussia, Pennsylvania 19406.
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pubmed:publicationType |
Journal Article
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