Synthesis and cannabinoid-1 receptor binding affinity of conformationally constrained analogs of taranabant

Bioorganic & Medicinal Chemistry Letters
Ihor E KopkaWilliam Hagmann

Abstract

The design, synthesis, and binding activity of ring constrained analogs of the acyclic cannabinoid-1 receptor (CB1R) inverse agonist taranabant 1 are described. The initial inspiration for these taranabant derivatives was its conformation 1a, determined by (1)H NMR, X-ray, and molecular modeling. The constrained analogs were all much less potent than their acyclic parent structure. The results obtained are discussed in the context of a predicted binding of 1 to a homology model of CB1R.

References

May 18, 2005·Drug Discovery Today·Jos H M Lange, Chris G Kruse
Mar 3, 2009·Expert Opinion on Emerging Drugs·David R Janero, Alexandros Makriyannis

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Citations

Jan 18, 2013·Chemistry : a European Journal·Tobias AnknerPaul Helquist
Sep 29, 2011·Organic & Biomolecular Chemistry·Su-Jeong LeeChang-Woo Cho

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