Abstract
The enantiomers of the leukotriene D4 antagonist 3-[[[3-[2-(7-chloroquinolin-2-yl)-(E)-ethenyl]phenyl] [[3-(dimethylamino)-3-oxopropyl]thio]methyl]thio]propionic acid (L-660,711)(MK-571) have been prepared, their absolute stereochemistry has been assigned as S for (+)-1 and R for (-)-1 by X-ray analysis of a synthetic intermediate (5), and the biological activity of the enantiomers has been explored. Unexpectedly, the enantiomers are both comparably biologically active with (+)-1 slightly more intrinsically active at the LTD4 receptor in vitro.
MeSH terms
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Animals
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Binding, Competitive
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Cell Membrane / metabolism
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Chemical Phenomena
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Chemistry
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Guinea Pigs
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In Vitro Techniques
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Lung / metabolism
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Molecular Conformation
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Propionates / chemical synthesis*
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Propionates / chemistry
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Propionates / pharmacology
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Quinolines / chemical synthesis*
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Quinolines / chemistry
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Quinolines / pharmacology
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Receptors, Immunologic / antagonists & inhibitors*
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Receptors, Immunologic / drug effects
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Receptors, Immunologic / metabolism
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Receptors, Leukotriene
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SRS-A / antagonists & inhibitors*
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SRS-A / metabolism
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Propionates
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Quinolines
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Receptors, Immunologic
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Receptors, Leukotriene
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SRS-A
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verlukast