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Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists.

ABSTRACT: The crystal structures of four indole derivatives with various substituents at the 2-, 3- and 5-positions of the ring system are described, namely, ethyl 3-(5-chloro-2-phenyl-1H-indol-3-yl)-3-phenyl-propano-ate, C25H22ClNO2, (I), 2-bromo-3-(2-nitro-1-phenyl-eth-yl)-1H-indole, C16H13BrN2O2, (II), 5-meth-oxy-3-(2-nitro-1-phenyl-eth-yl)-2-phenyl-1H-indole, C23H20N2O3, (III), and 5-chloro-3-(2-nitro-1-phenyl-eth-yl)-2-phenyl-1H-indole, C22H17ClN2O2, (IV). The dominant inter-molecular inter-action in each case is an N-H?O hydrogen bond, which generates either chains or inversion dimers. Weak C-H?O, C-H?? and ?-? inter-actions occur in these structures but there is no consistent pattern amongst them. Two of these compounds act as modest enhancers of CB1 cannabanoid signalling and two are inactive.

SUBMITTER: Kerr JR

PROVIDER: S-EPMC4459378 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists.

Kerr Jamie R JR Trembleau Laurent L Storey John M D JM Wardell James L JL Harrison William T A WT

Acta crystallographica. Section E, Crystallographic communications 20150520 Pt 6

The crystal structures of four indole derivatives with various substituents at the 2-, 3- and 5-positions of the ring system are described, namely, ethyl 3-(5-chloro-2-phenyl-1H-indol-3-yl)-3-phenyl-propano-ate, C25H22ClNO2, (I), 2-bromo-3-(2-nitro-1-phenyl-eth-yl)-1H-indole, C16H13BrN2O2, (II), 5-meth-oxy-3-(2-nitro-1-phenyl-eth-yl)-2-phenyl-1H-indole, C23H20N2O3, (III), and 5-chloro-3-(2-nitro-1-phenyl-eth-yl)-2-phenyl-1H-indole, C22H17ClN2O2, (IV). The dominant inter-molecular inter-action in ...[more]

PMID: 26090143

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