Stereoselective synthesis of enantiopure N-substituted pyrrolidin-2,5-dione derivatives by 1,3-dipolar cycloaddition and assessment of their in vitro antioxidant and antibacterial activities |
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Authors: | Siwar Ghannay Sana Bakari Ameni Ghabi Adel Kadri Moncef Msaddek Kaïss Aouadi |
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Institution: | 1. Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Faculty of Sciences of Monastir, University of Monastir, Avenue de l’Environnement, 5000 Monastir, Tunisia;2. Laboratory of Plant Biotechnology Applied to Crop Improvement, Faculty of Science of Sfax, University of Sfax, B.P. 11713000 Sfax, Tunisia;3. College of Science and Arts in Baljurashi, Al Baha University, P.O. Box (1988), Al Baha, Saudi Arabia |
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Abstract: | 1,3-Dipolar cycloaddition between a chiral nitrone and N-substituted maleimides afforded unprecedented enantiopure spiro-fused heterocycles in good yields with a high enantio- and diastereoselectivity. The reaction was taking place on the less hindered face of the nitrone. The obtaining heterocycles were screened for their in vitro antioxidant properties and the results revealed that the potent antioxidant activity was generally recorded to compounds (3g) and (3e). The in vitro antibacterial activities of these two compounds were also investigated and the results demonstrated the strongest potential of compound (3g) against all the tested bacteria. Molecular properties were analyzed and showed good oral drug candidate like properties and that could be exploited as a potential antioxidant and antimicrobial agent. Finally, the preliminary results obtained from this investigation attempted to clarify if the structurally different side chains of active compounds interfere with their biological properties. |
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Keywords: | Pyrrolidin-2 5-dione Chiral nitrone DPPH ABTS Antioxidant activity Antibacterial activity |
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