Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1376252 | Bioorganic & Medicinal Chemistry Letters | 2007 | 4 Pages |
Abstract
A facile synthesis of 1-fluoro-1-deoxy-Δ8-THC analogs with side chains seven carbons in length, in the alkane/ene/yne- series (6, 5, and 4), was achieved from 1-fluoro-3,5-dimethoxybenzene (1). In vitro studies show that substitution by a fluorine has a significant detrimental effect on CB1 binding which is supported by in vivo testing. The implications of these results on the SAR of classical cannabinoids are discussed.
Graphical abstractSubstitution of the phenolic hydroxyl group of THCs by a fluorine (4, 5, 6) has a significant detrimental effect on CB1 binding affinity.Figure optionsDownload full-size imageDownload as PowerPoint slide
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Peter J. Crocker, Anu Mahadevan, Jenny L. Wiley, Billy R. Martin, Raj K. Razdan,