The role of fluorine substitution in the structure–activity relationships (SAR) of classical cannabinoids

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• 作者：Peter J. Crocker ; Anu Mahadevan ; Jenny L. Wiley ; Billy R. Martin ; Raj K. Razdan
• 关键词：Fluorine substitution ; Tetrahydrocannabinols ; CB1 binding affinity
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2007
• 期刊代码：10_0960894x
• 类别：ch
• 出版时间：15 March 2007
• 卷：17
• 期：6
• 页码：1504-1507
• 文件大小：130 K

摘要

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.