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
Article Menu

Article Versions

Export Article

Open AccessCommunication
Molecules 2010, 15(11), 8039-8047; doi:10.3390/molecules15118039

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
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 alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top