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3-Indolyl-1-naphthylmethanes: New Cannabimimetic Indoles Provide Evidence for Aromatic StackingInter

3-Indolyl-1-naphthylmethanes: New Cannabimimetic Indoles Provide Evidence for Aromatic StackingInter

  1. Quantum Dude
    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 carbonylgroup. Indoles 9–11 have significant (Ki=17–23 nM) receptor affinity, somewhat
    less than that of the corresponding naphthoylindoles (5, 15, 16). 2-Methyl-1-indoles 12–14 have little affinity for the CB1
    receptor, in contrast to 2-methyl-3-(1-naphthoyl)indoles 17–19, which have affinities comparable to those of 5, 15, 16. A cannabimimetic
    indene hydrocarbon (26) was synthesized and found to have Ki=264 nM. Molecular modeling and receptor docking
    studies of naphthoylindole 16, its 2-methylcongener (19) and indolyl-1-naphthylmethanes 11 and 14, combined with the receptor
    affinities of these cannabimimetic indoles, strongly suggest that these cannabinoid receptor ligands bind primarily by aromatic
    stacking interactions in the transmembrane helix 3-4-5-6 region of the CB1 receptor.