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Molecules 2009, 14(9), 3187-3197; doi:10.3390/molecules14093187
Communication

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

1,* , 1
,
1, 1, 1 and 2
1 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 2 Departamento de Princípios Ativos, Naturais e Toxicologia, Faculdade de Ciências Farmacêuticas – UNESP Rodovia Araraquara Jaú Km. 01, 14801-902, Araraquara, SP, Brazil
* Author to whom correspondence should be addressed.
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)
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Abstract

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.
Keywords: indolinone; pro-drug; anti-inflammatory; hydrolysis; diclofenac indolinone; pro-drug; anti-inflammatory; hydrolysis; diclofenac
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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