Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists

Research output: Contribution to journalArticle

4 Citations (Scopus)
9 Downloads (Pure)

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

Fingerprint

Cannabinoid Receptor Antagonists
indoles
Dimers
Hydrogen bonds
Crystal structure
Derivatives
crystal structure
methylidyne
dimers
interactions
inversions
hydrogen bonds
alpha-phenylindole
indole
Cannabinoids
rings

Keywords

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

Cite this

@article{c66a0958f56b4b87be6991bda92545c9,
title = "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-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.",
keywords = "crystal structure, indole, cannabinoid allosteric antagonist, N-H...O crystal structure",
author = "Kerr, {Jamie R.} and Laurent Trembleau and Storey, {John M. D.} and Wardell, {James L.} and Harrison, {William T. A.}",
note = "Acknowledgements 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.",
year = "2015",
month = "6",
doi = "10.1107/S2056989015008476",
language = "English",
volume = "71",
pages = "654--659",
journal = "Acta Crystallographica Section E: Structure Reports Online",
issn = "1600-5368",
publisher = "International Union of Crystallography",
number = "6",

}

TY - JOUR

T1 - Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists

AU - Kerr, Jamie R.

AU - Trembleau, Laurent

AU - Storey, John M. D.

AU - Wardell, James L.

AU - Harrison, William T. A.

N1 - Acknowledgements 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.

PY - 2015/6

Y1 - 2015/6

N2 - 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.

AB - 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.

KW - crystal structure

KW - indole

KW - cannabinoid allosteric antagonist

KW - N-H...O crystal structure

U2 - 10.1107/S2056989015008476

DO - 10.1107/S2056989015008476

M3 - Article

VL - 71

SP - 654

EP - 659

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

IS - 6

ER -