Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human Monoamine Oxidase inhibitors

A new series of 2-phenylbenzofuran derivatives were designed and synthesized to determine relevant structural features for the MAO inhibitory activity and selectivity. Methoxy substituents were introduced in the 2-phenyl ring, whereas the benzofuran moiety was not substituted or substituted at the p...

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Autores: Delogu, Giovanna Lucia, Kumar, Amit, Gatto, Gianluca, Bustelo Paz, Fernando, Saavedra, Lucía M, Rodríguez Franco, María Isabel, Laguna-Francia, Reyes, Viña Castelao, María Dolores
Tipo de recurso: artículo
Fecha de publicación:2021
País:España
Institución:Universidad de Santiago de Compostela (USC)
Repositorio:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
Idioma:inglés
OAI Identifier:oai:minerva.usc.gal:10347/32623
Acceso en línea:http://hdl.handle.net/10347/32623
Access Level:acceso abierto
Palabra clave:3209
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spelling Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human Monoamine Oxidase inhibitorsDelogu, Giovanna LuciaKumar, AmitGatto, GianlucaBustelo Paz, FernandoSaavedra, Lucía MRodríguez Franco, María IsabelLaguna-Francia, ReyesViña Castelao, María Dolores3209A new series of 2-phenylbenzofuran derivatives were designed and synthesized to determine relevant structural features for the MAO inhibitory activity and selectivity. Methoxy substituents were introduced in the 2-phenyl ring, whereas the benzofuran moiety was not substituted or substituted at the positions 5 or 7 with a nitro group. Substitution patterns on both the phenyl ring and the benzofuran moiety determine the affinity for MAO-A or MAO-B. The 2-(3-methoxyphenyl)-5-nitrobenzofuran 9 was the most potent MAO-B inhibitor (IC50 = 0.024 μM) identified in this series, whereas 7-nitro-2-phenylbenzofuran 7 was the most potent MAO-A inhibitor (IC50 = 0.168 μM), both acting as reversible inhibitors. The number and position of the methoxyl groups on the 2-phenyl ring, have an important influence on the inhibitory activity. Molecular docking studies confirmed the experimental results and highlighted the importance of key residues in enzyme inhibition.ElsevierUniversidade de Santiago de Compostela. Centro de Investigación en Medicina Molecular e Enfermidades CrónicasUniversidade de Santiago de Compostela. Departamento de Farmacoloxía, Farmacia e Tecnoloxía Farmacéutica20212021-01-0520212021-01-05journal articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10347/32623reponame:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostelainstname:Universidad de Santiago de Compostela (USC)InglésengAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 RTI2018-093955-B-C21 INNOVADORES COMPUESTOS NEUROGENICOS Y FOTOCONMUTABLES PARA ENFERMEDADES NEUROLOGICAS. DESARROLLO GUIADO POR UNA PLATAFORMA OMICA DE TOXICOLOGIA Y DE MECANISMOS DE ACCIONopen accesshttp://purl.org/coar/access_right/c_abf2© 2021 Elsevier Inc. All rights reservedhttps://creativecommons.org/licenses/by-nc-nd/4.0/deed.esinfo:eu-repo/semantics/openAccessoai:minerva.usc.gal:10347/326232026-06-15T12:47:27Z
dc.title.none.fl_str_mv Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human Monoamine Oxidase inhibitors
title Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human Monoamine Oxidase inhibitors
spellingShingle Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human Monoamine Oxidase inhibitors
Delogu, Giovanna Lucia
3209
title_short Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human Monoamine Oxidase inhibitors
title_full Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human Monoamine Oxidase inhibitors
title_fullStr Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human Monoamine Oxidase inhibitors
title_full_unstemmed Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human Monoamine Oxidase inhibitors
title_sort Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human Monoamine Oxidase inhibitors
dc.creator.none.fl_str_mv Delogu, Giovanna Lucia
Kumar, Amit
Gatto, Gianluca
Bustelo Paz, Fernando
Saavedra, Lucía M
Rodríguez Franco, María Isabel
Laguna-Francia, Reyes
Viña Castelao, María Dolores
author Delogu, Giovanna Lucia
author_facet Delogu, Giovanna Lucia
Kumar, Amit
Gatto, Gianluca
Bustelo Paz, Fernando
Saavedra, Lucía M
Rodríguez Franco, María Isabel
Laguna-Francia, Reyes
Viña Castelao, María Dolores
author_role author
author2 Kumar, Amit
Gatto, Gianluca
Bustelo Paz, Fernando
Saavedra, Lucía M
Rodríguez Franco, María Isabel
Laguna-Francia, Reyes
Viña Castelao, María Dolores
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade de Santiago de Compostela. Centro de Investigación en Medicina Molecular e Enfermidades Crónicas
Universidade de Santiago de Compostela. Departamento de Farmacoloxía, Farmacia e Tecnoloxía Farmacéutica
dc.subject.none.fl_str_mv 3209
topic 3209
description A new series of 2-phenylbenzofuran derivatives were designed and synthesized to determine relevant structural features for the MAO inhibitory activity and selectivity. Methoxy substituents were introduced in the 2-phenyl ring, whereas the benzofuran moiety was not substituted or substituted at the positions 5 or 7 with a nitro group. Substitution patterns on both the phenyl ring and the benzofuran moiety determine the affinity for MAO-A or MAO-B. The 2-(3-methoxyphenyl)-5-nitrobenzofuran 9 was the most potent MAO-B inhibitor (IC50 = 0.024 μM) identified in this series, whereas 7-nitro-2-phenylbenzofuran 7 was the most potent MAO-A inhibitor (IC50 = 0.168 μM), both acting as reversible inhibitors. The number and position of the methoxyl groups on the 2-phenyl ring, have an important influence on the inhibitory activity. Molecular docking studies confirmed the experimental results and highlighted the importance of key residues in enzyme inhibition.
publishDate 2021
dc.date.none.fl_str_mv 2021
2021-01-05
2021
2021-01-05
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10347/32623
url http://hdl.handle.net/10347/32623
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 RTI2018-093955-B-C21 INNOVADORES COMPUESTOS NEUROGENICOS Y FOTOCONMUTABLES PARA ENFERMEDADES NEUROLOGICAS. DESARROLLO GUIADO POR UNA PLATAFORMA OMICA DE TOXICOLOGIA Y DE MECANISMOS DE ACCION
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
© 2021 Elsevier Inc. All rights reserved
https://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
© 2021 Elsevier Inc. All rights reserved
https://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
instname:Universidad de Santiago de Compostela (USC)
instname_str Universidad de Santiago de Compostela (USC)
reponame_str Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
collection Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869402717574660096
score 15.812455

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