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Crystal structure of 4,4′-bis­[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl

The title compound, C(28)H(32)N(2), (I), is one of a second generation of compounds designed and synthesized based on a very potent and selective α9α10 nicotinic acetyl­choline receptor antagonist ZZ161C {1,1′-[[1,1′-biphen­yl]-4,4′-diylbis(prop-2-yne-3,1-di­yl)]bis­(3,4-di­methyl­pyridin-1-ium) bro...

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Autores principales: Walbaum, Anqi, Fifer, E. Kim, Parkin, Sean, Crooks, Peter A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5458311/
https://www.ncbi.nlm.nih.gov/pubmed/28638646
http://dx.doi.org/10.1107/S2056989017007277
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author Walbaum, Anqi
Fifer, E. Kim
Parkin, Sean
Crooks, Peter A.
author_facet Walbaum, Anqi
Fifer, E. Kim
Parkin, Sean
Crooks, Peter A.
author_sort Walbaum, Anqi
collection PubMed
description The title compound, C(28)H(32)N(2), (I), is one of a second generation of compounds designed and synthesized based on a very potent and selective α9α10 nicotinic acetyl­choline receptor antagonist ZZ161C {1,1′-[[1,1′-biphen­yl]-4,4′-diylbis(prop-2-yne-3,1-di­yl)]bis­(3,4-di­methyl­pyridin-1-ium) bromide}, which has shown analgesic effects in a chemotherapy-induced neuropathy animal model. Compound (I) was synthesized by the reaction of 4,4′-bis­(3-bromo­prop-1-yn-1-yl)-1,1′-biphenyl with piperidine at room temperature in aceto­nitrile. The single-crystal used for X-ray analysis was obtained by dissolving (I) in a mixture of di­chloro­methane and methanol, followed by slow evaporation of the solvent. In the crystal of (I), the biphenyl moiety has a twisted conformation, with a dihedral angle of 25.93 (4)° between the benzene rings. Both piperidine head groups in (I) are in the chair conformation and are oriented so that the N-atom lone pairs of each piperidine group point away from the central biphenyl moiety.
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spelling pubmed-54583112017-06-21 Crystal structure of 4,4′-bis­[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl Walbaum, Anqi Fifer, E. Kim Parkin, Sean Crooks, Peter A. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(28)H(32)N(2), (I), is one of a second generation of compounds designed and synthesized based on a very potent and selective α9α10 nicotinic acetyl­choline receptor antagonist ZZ161C {1,1′-[[1,1′-biphen­yl]-4,4′-diylbis(prop-2-yne-3,1-di­yl)]bis­(3,4-di­methyl­pyridin-1-ium) bromide}, which has shown analgesic effects in a chemotherapy-induced neuropathy animal model. Compound (I) was synthesized by the reaction of 4,4′-bis­(3-bromo­prop-1-yn-1-yl)-1,1′-biphenyl with piperidine at room temperature in aceto­nitrile. The single-crystal used for X-ray analysis was obtained by dissolving (I) in a mixture of di­chloro­methane and methanol, followed by slow evaporation of the solvent. In the crystal of (I), the biphenyl moiety has a twisted conformation, with a dihedral angle of 25.93 (4)° between the benzene rings. Both piperidine head groups in (I) are in the chair conformation and are oriented so that the N-atom lone pairs of each piperidine group point away from the central biphenyl moiety. International Union of Crystallography 2017-05-19 /pmc/articles/PMC5458311/ /pubmed/28638646 http://dx.doi.org/10.1107/S2056989017007277 Text en © Walbaum et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Walbaum, Anqi
Fifer, E. Kim
Parkin, Sean
Crooks, Peter A.
Crystal structure of 4,4′-bis­[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl
title Crystal structure of 4,4′-bis­[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl
title_full Crystal structure of 4,4′-bis­[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl
title_fullStr Crystal structure of 4,4′-bis­[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl
title_full_unstemmed Crystal structure of 4,4′-bis­[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl
title_short Crystal structure of 4,4′-bis­[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl
title_sort crystal structure of 4,4′-bis­[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5458311/
https://www.ncbi.nlm.nih.gov/pubmed/28638646
http://dx.doi.org/10.1107/S2056989017007277
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