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Pelanserin: 3-[3-(4-phenyl­piperazin-1-yl)prop­yl]quinazoline-2,4(1H,3H)-dione

The title compound, C(21)H(24)N(4)O(2), is a potent serotonin 5-HT(2) and α(1)-adrenoceptor antagonist. The n-propyl chain links the quinazolinedione heterocycle and the phenyl­piperazine group in which the benzene ring is equatorially located and the piperazine ring has the expected chair conformat...

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Detalles Bibliográficos
Autores principales: Aguirre Hernández, Gerardo, Somanathan, Ratnasamy, Bernès, Sylvain
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4158516/
https://www.ncbi.nlm.nih.gov/pubmed/25249922
http://dx.doi.org/10.1107/S160053681401602X
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author Aguirre Hernández, Gerardo
Somanathan, Ratnasamy
Bernès, Sylvain
author_facet Aguirre Hernández, Gerardo
Somanathan, Ratnasamy
Bernès, Sylvain
author_sort Aguirre Hernández, Gerardo
collection PubMed
description The title compound, C(21)H(24)N(4)O(2), is a potent serotonin 5-HT(2) and α(1)-adrenoceptor antagonist. The n-propyl chain links the quinazolinedione heterocycle and the phenyl­piperazine group in which the benzene ring is equatorially located and the piperazine ring has the expected chair conformation. The dihedral angle between the planes of the benzene ring and the quinazolinedione ring system is 74.1 (1)°. In the crystal, mol­ecules form centrosymmetric dimers through R (2) (2)(8) hydrogen-bonded rings involving the amine and one carbonyl group of the quinazolinedione moiety. These dimers are extended into chains extending along the a-axis direction through expanded centrosymmetric cyclic C—H⋯O associations involving the second carbonyl group, giving R (2) (2)(20) and R (1) (2)(7) motifs.
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spelling pubmed-41585162014-09-23 Pelanserin: 3-[3-(4-phenyl­piperazin-1-yl)prop­yl]quinazoline-2,4(1H,3H)-dione Aguirre Hernández, Gerardo Somanathan, Ratnasamy Bernès, Sylvain Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(21)H(24)N(4)O(2), is a potent serotonin 5-HT(2) and α(1)-adrenoceptor antagonist. The n-propyl chain links the quinazolinedione heterocycle and the phenyl­piperazine group in which the benzene ring is equatorially located and the piperazine ring has the expected chair conformation. The dihedral angle between the planes of the benzene ring and the quinazolinedione ring system is 74.1 (1)°. In the crystal, mol­ecules form centrosymmetric dimers through R (2) (2)(8) hydrogen-bonded rings involving the amine and one carbonyl group of the quinazolinedione moiety. These dimers are extended into chains extending along the a-axis direction through expanded centrosymmetric cyclic C—H⋯O associations involving the second carbonyl group, giving R (2) (2)(20) and R (1) (2)(7) motifs. International Union of Crystallography 2014-07-23 /pmc/articles/PMC4158516/ /pubmed/25249922 http://dx.doi.org/10.1107/S160053681401602X Text en © Aguirre Hernández et al. 2014 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Aguirre Hernández, Gerardo
Somanathan, Ratnasamy
Bernès, Sylvain
Pelanserin: 3-[3-(4-phenyl­piperazin-1-yl)prop­yl]quinazoline-2,4(1H,3H)-dione
title Pelanserin: 3-[3-(4-phenyl­piperazin-1-yl)prop­yl]quinazoline-2,4(1H,3H)-dione
title_full Pelanserin: 3-[3-(4-phenyl­piperazin-1-yl)prop­yl]quinazoline-2,4(1H,3H)-dione
title_fullStr Pelanserin: 3-[3-(4-phenyl­piperazin-1-yl)prop­yl]quinazoline-2,4(1H,3H)-dione
title_full_unstemmed Pelanserin: 3-[3-(4-phenyl­piperazin-1-yl)prop­yl]quinazoline-2,4(1H,3H)-dione
title_short Pelanserin: 3-[3-(4-phenyl­piperazin-1-yl)prop­yl]quinazoline-2,4(1H,3H)-dione
title_sort pelanserin: 3-[3-(4-phenyl­piperazin-1-yl)prop­yl]quinazoline-2,4(1h,3h)-dione
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4158516/
https://www.ncbi.nlm.nih.gov/pubmed/25249922
http://dx.doi.org/10.1107/S160053681401602X
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