L-Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities
A study was planned to synthesize the phthalimide derivatives as phthalimides have versatile biological activities. To synthesize the phthalimide derivatives, initially the reaction was optimized with various catalysts, and L-proline was found to be the best catalyst as it provided excellent yield....
Saved in:
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley
2018-01-01
|
| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2018/5198325 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832564486749290496 |
|---|---|
| author | Shagufta Perveen Raha Orfali |
| author_facet | Shagufta Perveen Raha Orfali |
| author_sort | Shagufta Perveen |
| collection | DOAJ |
| description | A study was planned to synthesize the phthalimide derivatives as phthalimides have versatile biological activities. To synthesize the phthalimide derivatives, initially the reaction was optimized with various catalysts, and L-proline was found to be the best catalyst as it provided excellent yield. A series of phthalimide derivatives was synthesized by facile one-top reaction of phthalic acid with aryl amines under mild reaction conditions in the presence of L-proline as catalyst. Products were obtained in excellent yields and structurally characterized by 1H, 13C NMR, and mass spectral data. Products 1–7 were evaluated for antioxidant, anti-inflammatory, and lipoxygenase enzyme inhibition activities. Compounds 1 and 4 showed potent antioxidant activity under DPPH with IC50 values 27.3 and 25.0 μM when compared with the standard BHA (IC50 = 44.2 μM), respectively. Compounds 1 and 4 further showed strong lipoxygenase inhibition activity with IC50 values 21.34 and 20.45 μM when compared with standard baicalein (IC50 = 22.60 μM), respectively. Compound 2 was found to be promising and about equal to the used standard aspirin in the inhibition of bovine serum albumin denaturation, while other compounds showed weak-to-moderate % inhibition. |
| format | Article |
| id | doaj-art-8ea2b8ed25514f30b20f4120982ffe37 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2018-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-8ea2b8ed25514f30b20f4120982ffe372025-02-03T01:11:00ZengWileyJournal of Chemistry2090-90632090-90712018-01-01201810.1155/2018/51983255198325L-Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition ActivitiesShagufta Perveen0Raha Orfali1Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaA study was planned to synthesize the phthalimide derivatives as phthalimides have versatile biological activities. To synthesize the phthalimide derivatives, initially the reaction was optimized with various catalysts, and L-proline was found to be the best catalyst as it provided excellent yield. A series of phthalimide derivatives was synthesized by facile one-top reaction of phthalic acid with aryl amines under mild reaction conditions in the presence of L-proline as catalyst. Products were obtained in excellent yields and structurally characterized by 1H, 13C NMR, and mass spectral data. Products 1–7 were evaluated for antioxidant, anti-inflammatory, and lipoxygenase enzyme inhibition activities. Compounds 1 and 4 showed potent antioxidant activity under DPPH with IC50 values 27.3 and 25.0 μM when compared with the standard BHA (IC50 = 44.2 μM), respectively. Compounds 1 and 4 further showed strong lipoxygenase inhibition activity with IC50 values 21.34 and 20.45 μM when compared with standard baicalein (IC50 = 22.60 μM), respectively. Compound 2 was found to be promising and about equal to the used standard aspirin in the inhibition of bovine serum albumin denaturation, while other compounds showed weak-to-moderate % inhibition.http://dx.doi.org/10.1155/2018/5198325 |
| spellingShingle | Shagufta Perveen Raha Orfali L-Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities Journal of Chemistry |
| title | L-Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities |
| title_full | L-Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities |
| title_fullStr | L-Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities |
| title_full_unstemmed | L-Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities |
| title_short | L-Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities |
| title_sort | l proline catalyzed synthesis of phthalimide derivatives and evaluation of their antioxidant anti inflammatory and lipoxygenase inhibition activities |
| url | http://dx.doi.org/10.1155/2018/5198325 |
| work_keys_str_mv | AT shaguftaperveen lprolinecatalyzedsynthesisofphthalimidederivativesandevaluationoftheirantioxidantantiinflammatoryandlipoxygenaseinhibitionactivities AT rahaorfali lprolinecatalyzedsynthesisofphthalimidederivativesandevaluationoftheirantioxidantantiinflammatoryandlipoxygenaseinhibitionactivities |