Next Article in Journal
The Apoptotic Effect of 1’S-1’-Acetoxychavicol Acetate from Alpinia Conchigera on Human Cancer Cells
Previous Article in Journal
Recent Advance in Heterocyclic Organozinc and Organomanganese Compounds; Direct Synthetic Routes and Application in Organic Synthesis
Molecules 2010, 15(11), 8039-8047; doi:10.3390/molecules15118039
Communication

Synthesis, Characterization and Pharmacological Evaluation of 1-(2-Chloro-6-Fluorophenyl)-5-Methylindolin-2-One: A New Anti-Inflammatory Compound with Reduced Gastric Ulceration Properties

1,* , 1, 1, 1, 2 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: 25 September 2010 / Revised: 3 November 2010 / Accepted: 5 November 2010 / Published: 8 November 2010
Download PDF [174 KB, uploaded 18 June 2014]

Abstract

The new compound 1-(2-chloro-6-fluorophenyl)-5-methylindolin-2-one (1), designed using the prodrug approach, was easily obtained in 85% yield and characterized by nuclear magnetic resonance, elemental analysis, mass spectrometry and infrared spectroscopy. The lactam 1 showed anti-inflammatory and analgesic activity comparable to that of the COX-2 inhibitor lumiracoxib, without gastro-ulceration effects. Stability studies demonstrated that the lactam function was stable and did not hydrolyze in pH 1.2 or 7.4. Furthermore, using a thioglycollate-induced peritonitis model, compound 1 was shown to inhibit cell migration by 50.4%, while lumiracoxib inhibited it by 18%. This compound represents a new non-ulcerogenic prototype for the treatment of chronic inflammatory diseases.
Keywords: pro-drug; lactam; lumiracoxib; anti-inflammatory pro-drug; lactam; lumiracoxib; anti-inflammatory
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
MDPI and ACS Style

Dos Santos, J.L.; Chelucci, R.; Chiquetto, R.; Chung, M.C.; Campos, M.L.; Peccinini, R.G. Synthesis, Characterization and Pharmacological Evaluation of 1-(2-Chloro-6-Fluorophenyl)-5-Methylindolin-2-One: A New Anti-Inflammatory Compound with Reduced Gastric Ulceration Properties. Molecules 2010, 15, 8039-8047.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert