Recent advances in the synthesis of endocannabinoid related ligands.
Chem Phys Lipids
; 121(1-2): 21-33, 2002 Dec 31.
Article
de En
| MEDLINE
| ID: mdl-12505687
ABSTRACT
The chemical strategies used for the synthesis of various ligands related to the endocannabinoid system namely anandamide (AEA), 2-arachidonylglycerol (2-Ara-Gl), CB1/(vanilloid receptors) VR1, anandamide membrane transporter (AMT) and fatty acid amide hydrolase (FAAH) are described in this review. In general, the chemical synthesis of analogs with changes in the head group of AEA was quite straightforward involving the conversion of an acid to an amide or an ester. Analogs which had modifications in the end pentyl chain were more difficult to synthesize and required multistep synthetic sequences to prepare the target compounds. A facile total synthesis of 2-Ara-Gl was reported and an HPLC procedure for its identification and quantification was developed, but because of the instability of 2-Ara-Gl another synthesis was developed so that it can be stored as the more stable phenylboronate ester. Similarly the chemical synthesis of various ligands in the remaining areas of CB1/VR1, AMT and FAAH are described. A summary of the present state of knowledge about the SAR in each area is presented to help in the design and synthesis of novel ligands for the future.
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Collection:
01-internacional
Base de données:
MEDLINE
Sujet principal:
Acides gras insaturés
Limites:
Animals
Langue:
En
Journal:
Chem Phys Lipids
Année:
2002
Type de document:
Article
Pays d'affiliation:
États-Unis d'Amérique