Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists

Jamie R. Kerr; Laurent Trembleau; John M. D. Storey; James L. Wardell; William T. A. Harrison

doi:10.1107/S2056989015008476

Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists

Jamie R. Kerr, Laurent Trembleau, John M. D. Storey, James L. Wardell, William T. A. Harrison

Chemistry

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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 language	English
Pages (from-to)	654-659
Number of pages	6
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	6
Early online date	20 May 2015
DOIs	https://doi.org/10.1107/S2056989015008476
Publication status	Published - Jun 2015

Keywords

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

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Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists
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Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists: CCDC 1062393: 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
DOI: 10.5517/cc14nhr1
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
DOI: 10.5517/cc14nhny
Dataset
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
DOI: 10.5517/cc14nhq0
Dataset

Cite this

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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 = jun,

doi = "10.1107/S2056989015008476",

language = "English",

volume = "71",

pages = "654--659",

journal = "Acta Crystallographica Section E: Structure Reports Online",

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publisher = "International Union of Crystallography",

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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 -

Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists

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Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists: CCDC 1062393: Experimental Crystal Structure Determination

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

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

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