Abstract
Two novel methyl-substituted arachidonic acid derivatives were prepared in an enantioselective manner from commercially available chiral building blocks, and were found to be excellent templates for the development of (13S)-methyl-substituted anandamide analogues. One of the compounds synthesized, namely, (13S,5Z,8Z,11Z,14Z)-13-methyl-eicosa-5,8,11,14-tetraenoic acid N-(2-hydroxyethyl)amide, is an endocannabinoid analogue with remarkably high affinity for the CB1 cannabinoid receptor.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkylation
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Arachidonic Acid / chemical synthesis*
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Arachidonic Acid / chemistry
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Arachidonic Acids / chemical synthesis*
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Arachidonic Acids / chemistry
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Cannabinoid Receptor Modulators / chemistry*
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Cannabinoid Receptor Modulators / metabolism
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Endocannabinoids*
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Magnetic Resonance Spectroscopy
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Models, Molecular
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Receptor, Cannabinoid, CB1 / chemistry*
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Receptor, Cannabinoid, CB1 / metabolism
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Stereoisomerism
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Structure-Activity Relationship
Substances
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(13S,5Z,8Z,11Z,14Z)-13-methyl-eicosa-5,8,11,14-tetraenoic acid N-(2-hydroxyethyl)amide
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Arachidonic Acids
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Cannabinoid Receptor Modulators
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Endocannabinoids
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Receptor, Cannabinoid, CB1
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Arachidonic Acid