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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

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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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Author to whom correspondence should be addressed.
Molecules 2010, 15(11), 8039-8047; https://doi.org/10.3390/molecules15118039
Received: 25 September 2010 / Revised: 3 November 2010 / Accepted: 5 November 2010 / Published: 8 November 2010
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. View Full-Text
Keywords: pro-drug; lactam; lumiracoxib; anti-inflammatory pro-drug; lactam; lumiracoxib; anti-inflammatory
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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. https://doi.org/10.3390/molecules15118039

AMA Style

Dos Santos JL, Chelucci R, Chiquetto R, Chung MC, Campos ML, Peccinini RG. 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(11):8039-8047. https://doi.org/10.3390/molecules15118039

Chicago/Turabian Style

Dos Santos, Jean Leandro; Chelucci, Rafael; Chiquetto, Richard; Chung, Man Chin; Campos, Michel Leandro; Peccinini, Rosangela Gonçalves. 2010. "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 15, no. 11: 8039-8047. https://doi.org/10.3390/molecules15118039

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