3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB 1 cannabinoid receptor

JW Huffman, R Mabon, MJ Wu, J Lu, R Hart…

Index: Huffman, John W.; Mabon, Ross; Wu, Ming-Jung; Lu, Jianzhong; Hart, Richard; Hurst, Dow P.; Reggio, Patricia H.; Wiley, Jenny L.; Martin, Billy R. Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 4 p. 539 - 549

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Citation Number: 125

Abstract

A series of 1-pentyl-1H-indol-3-yl-(1-naphthyl) methanes (9–11) and 2-methyl-1-pentyl-1H- indol-3-yl-(1-naphthyl) methanes (12–14) have been synthesized to investigate the hypothesis that cannabimimetic 3-(1-naphthoyl) indoles interact with the CB1 receptor by hydrogen bonding to the carbonyl group. Indoles 9–11 have significant (Ki= 17–23nM) receptor affinity, somewhat less than that of the corresponding naphthoylindoles (5, 15, 16 ...