Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties

Detalhes bibliográficos
Autor(a) principal: Chin, Chung Man [UNESP]
Data de Publicação: 2009
Outros Autores: dos Santos, Jean Leandro [UNESP], Oliveira, Ednir Vizioli [UNESP], Blau, Lorena [UNESP], Menegon, Renato Farina [UNESP], Peccinini, Rosangela Goncalves [UNESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.3390/molecules14093187
http://hdl.handle.net/11449/7781
Resumo: The compound 1-(2,6-dichlorophenyl)indolin-2-one (1), planned as a pro-drug of diclofenac (2), was easily synthesized in 94% yield by an intramolecular reaction in the presence of coupling agent (i.e., EDC). Compound 1 showed anti-inflammatory and analgesic activity without gastro-ulcerogenic effects. The chemical and enzymatic hydrolysis profile of the lactam derivative 1 does not indicate conversion to diclofenac (2). This compound is a new non-ulcerogenic prototype for treatment of chronic inflammatory diseases.
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spelling Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Propertiesindolinonepro-druganti-inflammatoryhydrolysisdiclofenacThe compound 1-(2,6-dichlorophenyl)indolin-2-one (1), planned as a pro-drug of diclofenac (2), was easily synthesized in 94% yield by an intramolecular reaction in the presence of coupling agent (i.e., EDC). Compound 1 showed anti-inflammatory and analgesic activity without gastro-ulcerogenic effects. The chemical and enzymatic hydrolysis profile of the lactam derivative 1 does not indicate conversion to diclofenac (2). This compound is a new non-ulcerogenic prototype for treatment of chronic inflammatory diseases.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)UNESP, Fac Ciencias Farmaceut, Dept Farmacos & Medicamentos, Lapdesf Lab Pesquisa & Desenvolvimento Farmacos, BR-14801902 Araraquara, SP, BrazilUNESP, Fac Ciencias Farmaceut, Dept Principios Ativos Nat & Toxicol, BR-14801902 Araraquara, SP, BrazilUNESP, Fac Ciencias Farmaceut, Dept Farmacos & Medicamentos, Lapdesf Lab Pesquisa & Desenvolvimento Farmacos, BR-14801902 Araraquara, SP, BrazilUNESP, Fac Ciencias Farmaceut, Dept Principios Ativos Nat & Toxicol, BR-14801902 Araraquara, SP, BrazilFAPESP: 07/56115-0Molecular Diversity Preservation International-mdpiUniversidade Estadual Paulista (Unesp)Chin, Chung Man [UNESP]dos Santos, Jean Leandro [UNESP]Oliveira, Ednir Vizioli [UNESP]Blau, Lorena [UNESP]Menegon, Renato Farina [UNESP]Peccinini, Rosangela Goncalves [UNESP]2014-05-20T13:24:46Z2014-05-20T13:24:46Z2009-09-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article3187-3197application/pdfhttp://dx.doi.org/10.3390/molecules14093187Molecules. Basel: Molecular Diversity Preservation International-mdpi, v. 14, n. 9, p. 3187-3197, 2009.1420-3049http://hdl.handle.net/11449/778110.3390/molecules14093187WOS:000270201900007WOS000270201900007.pdf973433360797541310667434239290930000-0003-4141-0455Web of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengMolecules3.0980,855info:eu-repo/semantics/openAccess2024-06-24T14:51:24Zoai:repositorio.unesp.br:11449/7781Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T14:24:22.143138Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties
title Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties
spellingShingle Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties
Chin, Chung Man [UNESP]
indolinone
pro-drug
anti-inflammatory
hydrolysis
diclofenac
title_short Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties
title_full Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties
title_fullStr Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties
title_full_unstemmed Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties
title_sort Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties
author Chin, Chung Man [UNESP]
author_facet Chin, Chung Man [UNESP]
dos Santos, Jean Leandro [UNESP]
Oliveira, Ednir Vizioli [UNESP]
Blau, Lorena [UNESP]
Menegon, Renato Farina [UNESP]
Peccinini, Rosangela Goncalves [UNESP]
author_role author
author2 dos Santos, Jean Leandro [UNESP]
Oliveira, Ednir Vizioli [UNESP]
Blau, Lorena [UNESP]
Menegon, Renato Farina [UNESP]
Peccinini, Rosangela Goncalves [UNESP]
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade Estadual Paulista (Unesp)
dc.contributor.author.fl_str_mv Chin, Chung Man [UNESP]
dos Santos, Jean Leandro [UNESP]
Oliveira, Ednir Vizioli [UNESP]
Blau, Lorena [UNESP]
Menegon, Renato Farina [UNESP]
Peccinini, Rosangela Goncalves [UNESP]
dc.subject.por.fl_str_mv indolinone
pro-drug
anti-inflammatory
hydrolysis
diclofenac
topic indolinone
pro-drug
anti-inflammatory
hydrolysis
diclofenac
description The compound 1-(2,6-dichlorophenyl)indolin-2-one (1), planned as a pro-drug of diclofenac (2), was easily synthesized in 94% yield by an intramolecular reaction in the presence of coupling agent (i.e., EDC). Compound 1 showed anti-inflammatory and analgesic activity without gastro-ulcerogenic effects. The chemical and enzymatic hydrolysis profile of the lactam derivative 1 does not indicate conversion to diclofenac (2). This compound is a new non-ulcerogenic prototype for treatment of chronic inflammatory diseases.
publishDate 2009
dc.date.none.fl_str_mv 2009-09-01
2014-05-20T13:24:46Z
2014-05-20T13:24:46Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.3390/molecules14093187
Molecules. Basel: Molecular Diversity Preservation International-mdpi, v. 14, n. 9, p. 3187-3197, 2009.
1420-3049
http://hdl.handle.net/11449/7781
10.3390/molecules14093187
WOS:000270201900007
WOS000270201900007.pdf
9734333607975413
1066743423929093
0000-0003-4141-0455
url http://dx.doi.org/10.3390/molecules14093187
http://hdl.handle.net/11449/7781
identifier_str_mv Molecules. Basel: Molecular Diversity Preservation International-mdpi, v. 14, n. 9, p. 3187-3197, 2009.
1420-3049
10.3390/molecules14093187
WOS:000270201900007
WOS000270201900007.pdf
9734333607975413
1066743423929093
0000-0003-4141-0455
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Molecules
3.098
0,855
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 3187-3197
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International-mdpi
publisher.none.fl_str_mv Molecular Diversity Preservation International-mdpi
dc.source.none.fl_str_mv Web of Science
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
_version_ 1808128356230627328

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