| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1364580 | Bioorganic & Medicinal Chemistry Letters | 2008 | 4 Pages |
To explore the hydrophobic groove subsite within the CB1 cannabinoid receptor we have designed and synthesized a group of tail-substituted anandamide analogs. Our design involves the introduction of aryl or heterocyclic ring as terminal substituents that are connected to the last cis-arachidonyl double bond through aliphatic chains of variable lengths. Our results indicate that there are strict stereochemical requirements for the interaction of such analogs with the CB1 receptor. The optimal pharmacophore includes the phenyl, p-substituted phenyl, or 3-furyl substituents attached to the cis-double bond through a four methylene chain.
Graphical abstractSynthesis and evaluation of a series of anandamide analogs of variable chain lengths in which the terminal carbon is functionalized with a phenyl, substituted phenyl or heterocyclic group.Figure optionsDownload full-size imageDownload as PowerPoint slide
