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

dc.contributorUniversidade Estadual Paulista (UNESP)
dc.creatordos Santos, Jean Leandro
dc.creatorChelucci, Rafael
dc.creatorChiquetto, Richard
dc.creatorChin, Chung Man
dc.creatorCampos, Michel Leandro
dc.creatorPeccinini, Rosangela Goncalves
dc.date2014-05-20T13:24:46Z
dc.date2014-05-20T13:24:46Z
dc.date2010-11-01
dc.date.accessioned2017-04-05T20:01:16Z
dc.date.available2017-04-05T20:01:16Z
dc.identifierMolecules. Basel: Mdpi Ag, v. 15, n. 11, p. 8039-8047, 2010.
dc.identifier1420-3049
dc.identifierhttp://hdl.handle.net/11449/7776
dc.identifier10.3390/molecules15118039
dc.identifierWOS:000284582100034
dc.identifierWOS000284582100034.pdf
dc.identifierhttp://dx.doi.org/10.3390/molecules15118039
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/856325
dc.descriptionThe 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.
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.languageeng
dc.publisherMdpi Ag
dc.relationMolecules
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectpro-drug
dc.subjectlactam
dc.subjectlumiracoxib
dc.subjectanti-inflammatory
dc.titleSynthesis, Characterization and Pharmacological Evaluation of 1-(2-Chloro-6-Fluorophenyl)-5-Methylindolin-2-One: A New Anti-Inflammatory Compound with Reduced Gastric Ulceration Properties
dc.typeOtro


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