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  • Title: Synthesis of new anticancer and anti-inflammatory isoxazolines and aziridines from the natural (-)-deltoin.
    Author: Znati M, Debbabi M, Romdhane A, Ben Jannet H, Bouajila J.
    Journal: J Pharm Pharmacol; 2018 Dec; 70(12):1700-1712. PubMed ID: 30229910.
    Abstract:
    OBJECTIVES: This work describes the synthesis, the bioactivity and the structure-activity relationship of new derivatives from a natural coumarin. METHODS: (-)-Deltoin 1 and the corresponding isoxazolines and aziridines were characterized by spectroscopic means. The cytotoxic (HTC-116, IGROV-1 and OVCAR-3 cancer cell lines) and 5-lipoxygenase activity of (-)-deltoin 1 and its structural analogues have been evaluated. KEY FINDINGS: The phytochemical investigation of the ethyl acetate extract of the flowers of Ferula lutea (Poir.) Maire has led to the isolation of (-)-deltoin 1. A series of new isoxazoline 2a,a'-2f,f' and aziridine 3a,a'-3e,e' derivatives have been prepared by 1,3-dipolar cycloaddition. It has been found that the derivatives 2a (IC50 = 3.3 ± 0.1 μm), 3a,a' (IC50 = 5.9 ± 0.1 μm), 3b,b' (IC50 = 6.1 ± 0.7 μm) and 3c,c' (IC50 = 7.3 ± 0.9 μm) bearing a phenyl isoxazoline, a phenylaziridine, a 4-methlphenylaziridine and a 4-methoxyphenylaziridine, respectively, are more cytotoxic than (-)-deltoin 1 (IC50 = 14.3 ± 0.2 μm). The diastereoisomers in mixture (2f,f') with a 6-chloropyridin-2-yl system have shown the best anti-5-lipoxygenase activity (% inhibition = 53.1 ± 4.8% at 200 μm). CONCLUSIONS: Some analogues have been found more bioactive than deltoin 1. Their activity has been related to the nature of the added heterocycles. It would be interesting to evaluate their in-vivo activity.
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