Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists

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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-phenylpropanoate, C25H22ClNO2, (I), 2-bromo-3-(2-
nitro-1-phenylethyl)-1H-indole, C16H13BrN2O2, (II), 5-methoxy-3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole, C23H20N2O3, (III), and 5-chloro-3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole, C22H17ClN2O2, (IV). The dominant intermolecular interaction in each case is an N—H O hydrogen bond, which generates either chains or inversion dimers. Weak C—H O, C—H and – interactions 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.
Original languageEnglish
Pages (from-to)654-659
Number of pages6
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number6
Early online date20 May 2015
DOIs
Publication statusPublished - Jun 2015

Keywords

  • crystal structure
  • indole
  • cannabinoid allosteric antagonist
  • N-H...O crystal structure

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  • Datasets

    Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists: CCDC 1062392: Experimental Crystal Structure Determination

    Kerr, J. R. (Contributor), Trembleau, L. (Contributor), Storey, J. (Contributor), Wardell, J. L. (Contributor) & Harrison, W. (Contributor), Cambridge Crystallographic Data Centre, 29 Apr 2015

    Dataset

    Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists: CCDC 1062391: Experimental Crystal Structure Determination

    Kerr, J. R. (Contributor), Trembleau, L. (Contributor), Storey, J. (Contributor), Wardell, J. L. (Contributor) & Harrison, W. (Contributor), Cambridge Crystallographic Data Centre, 29 Apr 2015

    Dataset

    Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists: CCDC 1062390: Experimental Crystal Structure Determination

    Kerr, J. R. (Contributor), Trembleau, L. (Contributor), Storey, J. (Contributor), Wardell, J. L. (Contributor) & Harrison, W. (Contributor), Cambridge Crystallographic Data Centre, 29 Apr 2015

    Dataset

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