The Synthesis of N-Vanillyl-arachidonoyl-amide (Arvanil) and its Analogs: An Improved Procedure for the Synthesis of the Key Synthon Methyl 14-Hydroxy-(all- cis)-5,8,11-tetradecatrienoate

Several arvanil analogs were synthesized where the end n-pentyl chain was branched and carried substituents at the terminal end of the chain. A high yielding total synthesis of these analogs was developed from methyl hex-5-ynoate, which was converted to the synthon 6 in a facile five step sequence (...

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Bibliographic Details
Published inTetrahedron Vol. 56; no. 47; pp. 9195 - 9202
Main Authors Dasse, Olivier, Mahadevan, Anu, Han, Luning, Martin, Billy R., Marzo, Vincenzo Di, Razdan, Raj K.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.11.2000
Elsevier
Subjects
anandamide
arvanil analogs
cannabinoid receptor
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
vanilloid receptors
cannabinoid receptor
vanilloid receptors
anandamide
arvanil analogs
PHARMACOLOGICAL ACTIVITY
METABOLITES
BRAIN CONSTITUENT
18-HYDROXYEICOSATETRAENOIC ACIDS
CHAIN
NEURONS
CANNABINOID RECEPTOR AGONIST
OLVANIL
CAPSAICIN
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Summary:Several arvanil analogs were synthesized where the end n-pentyl chain was branched and carried substituents at the terminal end of the chain. A high yielding total synthesis of these analogs was developed from methyl hex-5-ynoate, which was converted to the synthon 6 in a facile five step sequence (overall yield, 33%). The pharmacological profile of these novel analogs suggests that they may be acting through a novel site of action for anandamide (arachidonylethanolamide, AEA).
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00877-2