Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists

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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
Issue number6
Early online date20 May 2015
Publication statusPublished - Jun 2015

Bibliographical note

We thank the EPSRC National Crystallography Service (University of Southampton) for the data collections and the EPSRC National Mass Spectrometry Service (University of Swansea) for the HRMS data. We thank John Low for carrying out the Cambridge Database survey.


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


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