Ethyl 4-{1-[(2,4-dinitro­phen­yl)hydrazono]eth­yl}-5-(2-naphthyl­methoxy­meth­yl)isoxazole-3-carboxyl­ate

The title compound, C(26)H(23)N(5)O(8), was prepared and its structure investigated to further develop a working hypothesis for the essential binding pharmacophore for ligands of the System Xc- transporter [Patel et al. (2004 ▶). Neuropharmacology, 46, 273–284]. The hydrazone group displays an E geo...

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Autores principales: Natale, Nicholas R., Szabon-Watola, Monica I., Twamley, Brendan, Bridges, Richard J., Patel, Sarjubhai, Rajale, Trideep
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968060/
https://www.ncbi.nlm.nih.gov/pubmed/21581603
http://dx.doi.org/10.1107/S1600536808041901
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author Natale, Nicholas R.
Szabon-Watola, Monica I.
Twamley, Brendan
Bridges, Richard J.
Patel, Sarjubhai
Rajale, Trideep
author_facet Natale, Nicholas R.
Szabon-Watola, Monica I.
Twamley, Brendan
Bridges, Richard J.
Patel, Sarjubhai
Rajale, Trideep
author_sort Natale, Nicholas R.
collection PubMed
description The title compound, C(26)H(23)N(5)O(8), was prepared and its structure investigated to further develop a working hypothesis for the essential binding pharmacophore for ligands of the System Xc- transporter [Patel et al. (2004 ▶). Neuropharmacology, 46, 273–284]. The hydrazone group displays an E geometry and the isoxazole double bond and C=N group of the hydrazone are in an s-cis relationship. The secondary amino NH group forms an intra­molecular N—H⋯O hydrogen bond to a ring nitro group. There is a dihedral angle of 44.27 (5)° between the isoxazole plane and the hydrazone group plane.
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spelling pubmed-29680602010-12-30 Ethyl 4-{1-[(2,4-dinitro­phen­yl)hydrazono]eth­yl}-5-(2-naphthyl­methoxy­meth­yl)isoxazole-3-carboxyl­ate Natale, Nicholas R. Szabon-Watola, Monica I. Twamley, Brendan Bridges, Richard J. Patel, Sarjubhai Rajale, Trideep Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(26)H(23)N(5)O(8), was prepared and its structure investigated to further develop a working hypothesis for the essential binding pharmacophore for ligands of the System Xc- transporter [Patel et al. (2004 ▶). Neuropharmacology, 46, 273–284]. The hydrazone group displays an E geometry and the isoxazole double bond and C=N group of the hydrazone are in an s-cis relationship. The secondary amino NH group forms an intra­molecular N—H⋯O hydrogen bond to a ring nitro group. There is a dihedral angle of 44.27 (5)° between the isoxazole plane and the hydrazone group plane. International Union of Crystallography 2008-12-17 /pmc/articles/PMC2968060/ /pubmed/21581603 http://dx.doi.org/10.1107/S1600536808041901 Text en © Natale et al. 2009 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
Natale, Nicholas R.
Szabon-Watola, Monica I.
Twamley, Brendan
Bridges, Richard J.
Patel, Sarjubhai
Rajale, Trideep
Ethyl 4-{1-[(2,4-dinitro­phen­yl)hydrazono]eth­yl}-5-(2-naphthyl­methoxy­meth­yl)isoxazole-3-carboxyl­ate
title Ethyl 4-{1-[(2,4-dinitro­phen­yl)hydrazono]eth­yl}-5-(2-naphthyl­methoxy­meth­yl)isoxazole-3-carboxyl­ate
title_full Ethyl 4-{1-[(2,4-dinitro­phen­yl)hydrazono]eth­yl}-5-(2-naphthyl­methoxy­meth­yl)isoxazole-3-carboxyl­ate
title_fullStr Ethyl 4-{1-[(2,4-dinitro­phen­yl)hydrazono]eth­yl}-5-(2-naphthyl­methoxy­meth­yl)isoxazole-3-carboxyl­ate
title_full_unstemmed Ethyl 4-{1-[(2,4-dinitro­phen­yl)hydrazono]eth­yl}-5-(2-naphthyl­methoxy­meth­yl)isoxazole-3-carboxyl­ate
title_short Ethyl 4-{1-[(2,4-dinitro­phen­yl)hydrazono]eth­yl}-5-(2-naphthyl­methoxy­meth­yl)isoxazole-3-carboxyl­ate
title_sort ethyl 4-{1-[(2,4-dinitro­phen­yl)hydrazono]eth­yl}-5-(2-naphthyl­methoxy­meth­yl)isoxazole-3-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968060/
https://www.ncbi.nlm.nih.gov/pubmed/21581603
http://dx.doi.org/10.1107/S1600536808041901
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AT patelsarjubhai ethyl4124dinitrophenylhydrazonoethyl52naphthylmethoxymethylisoxazole3carboxylate
AT rajaletrideep ethyl4124dinitrophenylhydrazonoethyl52naphthylmethoxymethylisoxazole3carboxylate

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