A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor

A convenient synthetic approach to novel functionalized bis(isoxazoles), the promising bivalent ligands of the AMPA receptor, was elaborated. It was based on the heterocyclization reactions of readily available electrophilic alkenes with the tetranitromethane-triethylamine complex. The structural di...

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Autores principales: Vasilenko, Dmitry A., Sadovnikov, Kirill S., Sedenkova, Kseniya N., Karlov, Dmitry S., Radchenko, Eugene V., Grishin, Yuri K., Rybakov, Victor B., Kuznetsova, Tamara S., Zamoyski, Vladimir L., Grigoriev, Vladimir V., Palyulin, Vladimir A., Averina, Elena B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8588558/
https://www.ncbi.nlm.nih.gov/pubmed/34770819
http://dx.doi.org/10.3390/molecules26216411
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author Vasilenko, Dmitry A.
Sadovnikov, Kirill S.
Sedenkova, Kseniya N.
Karlov, Dmitry S.
Radchenko, Eugene V.
Grishin, Yuri K.
Rybakov, Victor B.
Kuznetsova, Tamara S.
Zamoyski, Vladimir L.
Grigoriev, Vladimir V.
Palyulin, Vladimir A.
Averina, Elena B.
author_facet Vasilenko, Dmitry A.
Sadovnikov, Kirill S.
Sedenkova, Kseniya N.
Karlov, Dmitry S.
Radchenko, Eugene V.
Grishin, Yuri K.
Rybakov, Victor B.
Kuznetsova, Tamara S.
Zamoyski, Vladimir L.
Grigoriev, Vladimir V.
Palyulin, Vladimir A.
Averina, Elena B.
author_sort Vasilenko, Dmitry A.
collection PubMed
description A convenient synthetic approach to novel functionalized bis(isoxazoles), the promising bivalent ligands of the AMPA receptor, was elaborated. It was based on the heterocyclization reactions of readily available electrophilic alkenes with the tetranitromethane-triethylamine complex. The structural diversity of the synthesized compounds was demonstrated. In the electrophysiological experiments using the patch clamp technique on Purkinje neurons, the compound 1,4-phenylenedi(methylene)bis(5-aminoisoxazole-3-carboxylate) was shown to be highly potent positive modulator of the AMPA receptor, potentiating kainate-induced currents up to 70% at 10(−11) M.
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spelling pubmed-85885582021-11-13 A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor Vasilenko, Dmitry A. Sadovnikov, Kirill S. Sedenkova, Kseniya N. Karlov, Dmitry S. Radchenko, Eugene V. Grishin, Yuri K. Rybakov, Victor B. Kuznetsova, Tamara S. Zamoyski, Vladimir L. Grigoriev, Vladimir V. Palyulin, Vladimir A. Averina, Elena B. Molecules Article A convenient synthetic approach to novel functionalized bis(isoxazoles), the promising bivalent ligands of the AMPA receptor, was elaborated. It was based on the heterocyclization reactions of readily available electrophilic alkenes with the tetranitromethane-triethylamine complex. The structural diversity of the synthesized compounds was demonstrated. In the electrophysiological experiments using the patch clamp technique on Purkinje neurons, the compound 1,4-phenylenedi(methylene)bis(5-aminoisoxazole-3-carboxylate) was shown to be highly potent positive modulator of the AMPA receptor, potentiating kainate-induced currents up to 70% at 10(−11) M. MDPI 2021-10-23 /pmc/articles/PMC8588558/ /pubmed/34770819 http://dx.doi.org/10.3390/molecules26216411 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Vasilenko, Dmitry A.
Sadovnikov, Kirill S.
Sedenkova, Kseniya N.
Karlov, Dmitry S.
Radchenko, Eugene V.
Grishin, Yuri K.
Rybakov, Victor B.
Kuznetsova, Tamara S.
Zamoyski, Vladimir L.
Grigoriev, Vladimir V.
Palyulin, Vladimir A.
Averina, Elena B.
A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor
title A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor
title_full A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor
title_fullStr A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor
title_full_unstemmed A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor
title_short A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor
title_sort facile approach to bis(isoxazoles), promising ligands of the ampa receptor
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8588558/
https://www.ncbi.nlm.nih.gov/pubmed/34770819
http://dx.doi.org/10.3390/molecules26216411
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