Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 17, Issue 6, Pages 1504-1507Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2007.01.006
Keywords
fluorine substitution; tetrahydrocannabinols; CB1 binding affinity
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Funding
- NIDA NIH HHS [R37 DA003672, DA 05488, R01 DA003672-24A1, R01 DA005488, DA 03672, R01 DA003672] Funding Source: Medline
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A facile synthesis of 1-fluoro-1-deoxy-Delta(8)-THC analogs with side chains seven carbons in length, in the alkane/ene/yneseries (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. (c) 2007 Published by Elsevier Ltd.
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