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Design and synthesis of (13S)-methyl-substituted arachidonic acid analogues: templates for novel endocannabinoids.

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.

SUBMITTER: Papahatjis DP

PROVIDER: S-EPMC3786736 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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Design and synthesis of (13S)-methyl-substituted arachidonic acid analogues: templates for novel endocannabinoids.

Papahatjis Demetris P DP Nahmias Victoria R VR Nikas Spyros P SP Schimpgen Marion M Makriyannis Alexandros A

Chemistry (Weinheim an der Bergstrasse, Germany) 20100401 13

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. ...[more]

PMID: 20187040

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