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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
4
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pubmed:dateCreated |
1989-5-15
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pubmed:abstractText |
The structure-activity relationships of (E)-chalcone-4-carboxylic acids, which are retinoidal benzoic acids represented by R-Ph-X-Ph-COOH (4, X = -COCH = CH-), are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60. The activity was increased by the substitution of a bulky alkyl group(s) (R), and among such compounds, (E)-4-[3-(3,5-di-tert-butylphenyl)-3-oxo-1-propenyl]benzoic acid (Ch55) and (E)-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1 -propenyl]benzoic acid (Ch80) are several times more active than retinoic acid. Though the stable conformer of chalcone derivatives is linear (s-cis form), the conformationally restricted analogue 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphtho[2,3-b]py ran-2-yl)benzoic acid (Fv80) is more active than Ch80. While the effect of introduction of an oxygen atom varied, 4-[1-hydroxy-3-oxo-3-(5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2 - naphthalenyl)-1-propenyl]benzoic acid (Re80), regarded as a derivative of Ch80 with two additional hydroxyl groups, has very strong activity.
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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 |
Apr
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
32
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
834-40
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pubmed:dateRevised |
2008-11-21
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pubmed:meshHeading |
pubmed-meshheading:2704028-Carboxylic Acids,
pubmed-meshheading:2704028-Cell Differentiation,
pubmed-meshheading:2704028-Chalcone,
pubmed-meshheading:2704028-Chemical Phenomena,
pubmed-meshheading:2704028-Chemistry,
pubmed-meshheading:2704028-Chemistry, Physical,
pubmed-meshheading:2704028-Flavonoids,
pubmed-meshheading:2704028-Humans,
pubmed-meshheading:2704028-Leukemia, Promyelocytic, Acute,
pubmed-meshheading:2704028-Molecular Conformation,
pubmed-meshheading:2704028-Molecular Structure,
pubmed-meshheading:2704028-Physicochemical Phenomena,
pubmed-meshheading:2704028-Propiophenones,
pubmed-meshheading:2704028-Structure-Activity Relationship,
pubmed-meshheading:2704028-Tumor Cells, Cultured
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pubmed:year |
1989
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pubmed:articleTitle |
Retinobenzoic acids. 2. Structure-activity relationships of chalcone-4-carboxylic acids and flavone-4'-carboxylic acids.
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pubmed:affiliation |
Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.
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pubmed:publicationType |
Journal Article,
Comparative Study,
Research Support, Non-U.S. Gov't
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