Conformation and activity of tetrahydrofuran lignans and analogs as specific platelet-activating-factor antagonists

The six (racemic or meso) isomers of 3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)tetrahydrofuran and four corresponding desmethyl analogues were prepared and assayed as inhibitors of platelet activating factor (PAF) receptor binding to rabbit platelet plasma membranes. The inhibition by these isomers i...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1986-10, Vol.29 (10), p.1917-1921
Main Authors: Biftu, Tesfaye, Gamble, Nancy F, Doebber, Thomas, Hwang, San Bao, Shen, Tsung Ying, Snyder, James, Springer, James P, Stevenson, Robert
Format: Article
Language:English
Subjects:
Animals
Chemistry
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Furans - chemical synthesis
Furans - pharmacology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lignans
Molecular Conformation
Organic chemistry
Organic compounds
Physics
Plant Extracts - chemical synthesis
Plant Extracts - pharmacology
Platelet Activating Factor - antagonists & inhibitors
Preparations and properties
Rabbits
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
Structure-Activity Relationship
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Summary:The six (racemic or meso) isomers of 3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)tetrahydrofuran and four corresponding desmethyl analogues were prepared and assayed as inhibitors of platelet activating factor (PAF) receptor binding to rabbit platelet plasma membranes. The inhibition by these isomers is stereodependent and varies with the gross shape of the molecules as determined by the molecular mechanics program MM2. The most potent PAF antagonist in this group of compounds is trans-2,5-bis(3,4,5-trimethoxyphenyl)tetrahydrofuran (L-652,731, 14) with an IC50 of 0.02 microM.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00160a020