2-(Piperidin-4-yl)acetamides as potent inhibitors of soluble epoxide hydrolase with anti-inflammatory activity

The pharmacological inhibition of soluble epoxide hydrolase (sEH) has been suggested as a potential therapy for the treatment of pain and inflammatory diseases through the stabilization of endogenous epoxyeicosatrienoic acids. Numerous potent sEH inhibitors (sEHI) have been developed, however many c...

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Autores: Martín López, Juan, Codony, Sandra, Bartra, Clara, Morisseau, Christophe, Loza García, María Isabel, Sanfeliu, Coral, Hammock, Bruce D., Brea Floriani, José Manuel, Vázquez, Santiago
Tipo de documento: artigo
Data de publicação:2021
País:España
Recursos:Universidad de Santiago de Compostela (USC)
Repositório:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
Idioma:inglês
OAI Identifier:oai:minerva.usc.gal:10347/45078
Acesso em linha:https://hdl.handle.net/10347/45078
Access Level:Acceso aberto
Palavra-chave:Amide
Benzohomoadamantane
DMPK properties
Piperidine
Soluble epoxide hydrolase
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spelling 2-(Piperidin-4-yl)acetamides as potent inhibitors of soluble epoxide hydrolase with anti-inflammatory activityMartín López, JuanCodony, SandraBartra, ClaraMorisseau, ChristopheLoza García, María IsabelSanfeliu, CoralHammock, Bruce D.Brea Floriani, José ManuelVázquez, SantiagoAmideBenzohomoadamantaneDMPK propertiesPiperidineSoluble epoxide hydrolaseThe pharmacological inhibition of soluble epoxide hydrolase (sEH) has been suggested as a potential therapy for the treatment of pain and inflammatory diseases through the stabilization of endogenous epoxyeicosatrienoic acids. Numerous potent sEH inhibitors (sEHI) have been developed, however many contain highly lipophilic substituents limiting their availability. Recently, a new series of benzohomoadamantane-based ureas endowed with potent inhibitory activity for the human and murine sEH was reported. However, their very low microsomal stability prevented further development. Herein, a new series of benzohomoadamantane-based amides were synthetized, fully characterized, and evaluated as sEHI. Most of these amides were endowed with excellent inhibitory potencies. A selected compound displayed anti-inflammatory effects with higher effectiveness than the reference sEHI, TPPUMDPIUniversidade de Santiago de Compostela. Centro de Investigación en Medicina Molecular e Enfermidades Crónicas (CiMUS)Universidade de Santiago de Compostela. Departamento de Farmacoloxía, Farmacia e Tecnoloxía Farmacéutica20212021-12-1720212021-12-17journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10347/45078reponame: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 PID2020-118127RB-I00 SINTESIS DE COMPUESTOS CON MECANISMOS INNOVADORES CONTRA ENFERMEDADES NEURODEGENERATIVAS Y DOLOR NEUROPATICOAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-106285RB-C22 MODULACION DE LA EPOXIDO HIDROLASA SOLUBLE EN CEREBRO Y TEJIDOS PERIFERICOS: IMPLICACION EN LA NEUROINFLAMACION TEMPRANAAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 SAF2017-82771-R SINTESIS DE COMPUESTOS CON MECANISMOS INNOVADORES CONTRA ENFERMEDADES NEURODEGENERATIVASopen accesshttp://purl.org/coar/access_right/c_abf2© 2021 by the authors. 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/)http://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:minerva.usc.gal:10347/450782026-06-15T12:47:27Z
dc.title.none.fl_str_mv 2-(Piperidin-4-yl)acetamides as potent inhibitors of soluble epoxide hydrolase with anti-inflammatory activity
title 2-(Piperidin-4-yl)acetamides as potent inhibitors of soluble epoxide hydrolase with anti-inflammatory activity
spellingShingle 2-(Piperidin-4-yl)acetamides as potent inhibitors of soluble epoxide hydrolase with anti-inflammatory activity
Martín López, Juan
Amide
Benzohomoadamantane
DMPK properties
Piperidine
Soluble epoxide hydrolase
title_short 2-(Piperidin-4-yl)acetamides as potent inhibitors of soluble epoxide hydrolase with anti-inflammatory activity
title_full 2-(Piperidin-4-yl)acetamides as potent inhibitors of soluble epoxide hydrolase with anti-inflammatory activity
title_fullStr 2-(Piperidin-4-yl)acetamides as potent inhibitors of soluble epoxide hydrolase with anti-inflammatory activity
title_full_unstemmed 2-(Piperidin-4-yl)acetamides as potent inhibitors of soluble epoxide hydrolase with anti-inflammatory activity
title_sort 2-(Piperidin-4-yl)acetamides as potent inhibitors of soluble epoxide hydrolase with anti-inflammatory activity
dc.creator.none.fl_str_mv Martín López, Juan
Codony, Sandra
Bartra, Clara
Morisseau, Christophe
Loza García, María Isabel
Sanfeliu, Coral
Hammock, Bruce D.
Brea Floriani, José Manuel
Vázquez, Santiago
author Martín López, Juan
author_facet Martín López, Juan
Codony, Sandra
Bartra, Clara
Morisseau, Christophe
Loza García, María Isabel
Sanfeliu, Coral
Hammock, Bruce D.
Brea Floriani, José Manuel
Vázquez, Santiago
author_role author
author2 Codony, Sandra
Bartra, Clara
Morisseau, Christophe
Loza García, María Isabel
Sanfeliu, Coral
Hammock, Bruce D.
Brea Floriani, José Manuel
Vázquez, Santiago
author2_role author
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 (CiMUS)
Universidade de Santiago de Compostela. Departamento de Farmacoloxía, Farmacia e Tecnoloxía Farmacéutica
dc.subject.none.fl_str_mv Amide
Benzohomoadamantane
DMPK properties
Piperidine
Soluble epoxide hydrolase
topic Amide
Benzohomoadamantane
DMPK properties
Piperidine
Soluble epoxide hydrolase
description The pharmacological inhibition of soluble epoxide hydrolase (sEH) has been suggested as a potential therapy for the treatment of pain and inflammatory diseases through the stabilization of endogenous epoxyeicosatrienoic acids. Numerous potent sEH inhibitors (sEHI) have been developed, however many contain highly lipophilic substituents limiting their availability. Recently, a new series of benzohomoadamantane-based ureas endowed with potent inhibitory activity for the human and murine sEH was reported. However, their very low microsomal stability prevented further development. Herein, a new series of benzohomoadamantane-based amides were synthetized, fully characterized, and evaluated as sEHI. Most of these amides were endowed with excellent inhibitory potencies. A selected compound displayed anti-inflammatory effects with higher effectiveness than the reference sEHI, TPPU
publishDate 2021
dc.date.none.fl_str_mv 2021
2021-12-17
2021
2021-12-17
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/10347/45078
url https://hdl.handle.net/10347/45078
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 PID2020-118127RB-I00 SINTESIS DE COMPUESTOS CON MECANISMOS INNOVADORES CONTRA ENFERMEDADES NEURODEGENERATIVAS Y DOLOR NEUROPATICO
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-106285RB-C22 MODULACION DE LA EPOXIDO HIDROLASA SOLUBLE EN CEREBRO Y TEJIDOS PERIFERICOS: IMPLICACION EN LA NEUROINFLAMACION TEMPRANA
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 SAF2017-82771-R SINTESIS DE COMPUESTOS CON MECANISMOS INNOVADORES CONTRA ENFERMEDADES NEURODEGENERATIVAS
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
http://creativecommons.org/licenses/by/4.0/
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
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
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
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score 15,811543

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