Literature DB >> 16889960

1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors.

John W Huffman1, Lea W Padgett, Matthew L Isherwood, Jenny L Wiley, Billy R Martin.   

Abstract

Two series of 1-alkyl-2-aryl-4-(1-naphthoyl)pyrroles were synthesized and their affinities for the cannabinoid CB(1) and CB(2) receptors were determined. In the 2-phenyl series (5) the N-alkyl group was varied from n-propyl to n-heptyl. A second series of 23 1-pentyl-2-aryl-4-(1-naphthoyl)-pyrroles (6) was also prepared. Several compounds in both series have CB(1) receptor affinities in the 6-30nM range. The high affinities of these pyrrole derivatives relative to JWH-030 (1, R=C(5)H(11)) support the hypothesis that these pyrroles interact with the CB(1) receptor primarily by aromatic stacking.

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Year:  2006        PMID: 16889960     DOI: 10.1016/j.bmcl.2006.07.051

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  8 in total

1.  Severe toxicity following synthetic cannabinoid ingestion.

Authors:  J Lapoint; L P James; C L Moran; L S Nelson; R S Hoffman; J H Moran
Journal:  Clin Toxicol (Phila)       Date:  2011-10       Impact factor: 4.467

Review 2.  Marijuana-based drugs: innovative therapeutics or designer drugs of abuse?

Authors:  Kathryn A Seely; Paul L Prather; Laura P James; Jeffery H Moran
Journal:  Mol Interv       Date:  2011-02

3.  Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: steric and electronic effects of 4- and 8-halogenated naphthoyl substituents.

Authors:  Jenny L Wiley; Valerie J Smith; Jianhong Chen; Billy R Martin; John W Huffman
Journal:  Bioorg Med Chem       Date:  2012-01-30       Impact factor: 3.641

4.  1-Pentyl-3-phenylacetylindoles and JWH-018 share in vivo cannabinoid profiles in mice.

Authors:  Jenny L Wiley; Julie A Marusich; Billy R Martin; John W Huffman
Journal:  Drug Alcohol Depend       Date:  2011-11-27       Impact factor: 4.492

Review 5.  Moving around the molecule: relationship between chemical structure and in vivo activity of synthetic cannabinoids.

Authors:  Jenny L Wiley; Julie A Marusich; John W Huffman
Journal:  Life Sci       Date:  2013-09-23       Impact factor: 5.037

Review 6.  Cannabinoid receptor 2: potential role in immunomodulation and neuroinflammation.

Authors:  Slava Rom; Yuri Persidsky
Journal:  J Neuroimmune Pharmacol       Date:  2013-03-08       Impact factor: 4.147

7.  Acylation of N-p-Toluenesulfonylpyrrole Under Friedel-Crafts Conditions. Evidence for Organoaluminum Intermediates.

Authors:  John W Huffman; Valerie J Smith; Lea W Padgett
Journal:  Tetrahedron       Date:  2008-02-25       Impact factor: 2.457

8.  Discovery of High-Affinity Cannabinoid Receptors Ligands through a 3D-QSAR Ushered by Scaffold-Hopping Analysis.

Authors:  Giuseppe Floresta; Orapan Apirakkan; Antonio Rescifina; Vincenzo Abbate
Journal:  Molecules       Date:  2018-08-30       Impact factor: 4.411

  8 in total

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