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

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Lapdesf - Laboratório de Pesquisa e Desenvolvimento de Fármacos, Departamento de Fármacos e Medicamentos, Faculdade de Ciências Farmacêuticas – UNESP Rodovia Araraquara Jaú Km. 01, 14801-902, Araraquara, SP, Brazil
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Departamento de Princípios Ativos, Naturais e Toxicologia, Faculdade de Ciências Farmacêuticas – UNESP Rodovia Araraquara Jaú Km. 01, 14801-902, Araraquara, SP, Brazil
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Molecules 2009, 14(9), 3187-3197; https://doi.org/10.3390/molecules14093187
Received: 12 June 2009 / Revised: 7 August 2009 / Accepted: 13 August 2009 / Published: 26 August 2009
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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. View Full-Text
Keywords: indolinone; pro-drug; anti-inflammatory; hydrolysis; diclofenac indolinone; pro-drug; anti-inflammatory; hydrolysis; diclofenac
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MDPI and ACS Style

Chung, M.C.; Dos Santos, J.L.; Oliveira, E.V.; Blau, L.; Menegon, R.F.; Peccinini, R.G. Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties. Molecules 2009, 14, 3187-3197. https://doi.org/10.3390/molecules14093187

AMA Style

Chung MC, Dos Santos JL, Oliveira EV, Blau L, Menegon RF, Peccinini RG. Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties. Molecules. 2009; 14(9):3187-3197. https://doi.org/10.3390/molecules14093187

Chicago/Turabian Style

Chung, Man C., Jean L. Dos Santos, Ednir V. Oliveira, Lorena Blau, Renato F. Menegon, and Rosângela G. Peccinini 2009. "Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties" Molecules 14, no. 9: 3187-3197. https://doi.org/10.3390/molecules14093187

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