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
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 an...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2010-11-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/15/11/8039/ |
| _version_ | 1818778507753291776 |
|---|---|
| author | Michel Leandro Campos Jean Leandro dos Santos Rafael Chelucci Man Chin Chung Richard Chiquetto Rosangela Gonçalves Peccinini |
| author_facet | Michel Leandro Campos Jean Leandro dos Santos Rafael Chelucci Man Chin Chung Richard Chiquetto Rosangela Gonçalves Peccinini |
| author_sort | Michel Leandro Campos |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-18T11:45:50Z |
| format | Article |
| id | doaj.art-74c935c09da84240bf944f852e78e521 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-18T11:45:50Z |
| publishDate | 2010-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-74c935c09da84240bf944f852e78e5212022-12-21T21:09:17ZengMDPI AGMolecules1420-30492010-11-0115118039804710.3390/molecules15118039Synthesis, Characterization and Pharmacological Evaluation of 1-(2-Chloro-6-Fluorophenyl)-5-Methylindolin-2-One: A New Anti-Inflammatory Compound with Reduced Gastric Ulceration PropertiesMichel Leandro CamposJean Leandro dos SantosRafael ChelucciMan Chin ChungRichard ChiquettoRosangela Gonçalves PeccininiThe 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.http://www.mdpi.com/1420-3049/15/11/8039/pro-druglactamlumiracoxibanti-inflammatory |
| spellingShingle | Michel Leandro Campos Jean Leandro dos Santos Rafael Chelucci Man Chin Chung Richard Chiquetto Rosangela Gonçalves Peccinini 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 pro-drug lactam lumiracoxib anti-inflammatory |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | pro-drug lactam lumiracoxib anti-inflammatory |
| url | http://www.mdpi.com/1420-3049/15/11/8039/ |
| work_keys_str_mv | AT michelleandrocampos synthesischaracterizationandpharmacologicalevaluationof12chloro6fluorophenyl5methylindolin2oneanewantiinflammatorycompoundwithreducedgastriculcerationproperties AT jeanleandrodossantos synthesischaracterizationandpharmacologicalevaluationof12chloro6fluorophenyl5methylindolin2oneanewantiinflammatorycompoundwithreducedgastriculcerationproperties AT rafaelchelucci synthesischaracterizationandpharmacologicalevaluationof12chloro6fluorophenyl5methylindolin2oneanewantiinflammatorycompoundwithreducedgastriculcerationproperties AT manchinchung synthesischaracterizationandpharmacologicalevaluationof12chloro6fluorophenyl5methylindolin2oneanewantiinflammatorycompoundwithreducedgastriculcerationproperties AT richardchiquetto synthesischaracterizationandpharmacologicalevaluationof12chloro6fluorophenyl5methylindolin2oneanewantiinflammatorycompoundwithreducedgastriculcerationproperties AT rosangelagoncalvespeccinini synthesischaracterizationandpharmacologicalevaluationof12chloro6fluorophenyl5methylindolin2oneanewantiinflammatorycompoundwithreducedgastriculcerationproperties |