Journal
JOURNAL OF MOLECULAR STRUCTURE
Volume 1290, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.molstruc.2023.135892
Keywords
Anti-HepG2; Coumarin-isoxazole derivatives; [3+2] dipolar cycloaddition reaction; Apoptosis; Molecular docking
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A series of coumarin-isoxazole derivatives were synthesized and characterized, and their cytotoxicity against HepG2 cell lines and toxicity against Vero cell lines were evaluated. MC-16, a monoclinic crystal with P21/c space group, was confirmed by X-ray and 2D-NMR. Eight compounds exhibited varying levels of cytotoxicity against HepG2 cells, with MC-14 showing the strongest activity and inducing apoptosis. Docking results revealed effective protein interactions for the bioactive compounds.
In here, a series of coumarin-isoxazole derivatives were synthesized, characterized by spectroscopy technologies and evaluated for their cytotoxicity against HepG2 cell lines. Meanwhile, eight bioactive compounds were also evaluated for their toxicity on normal Vero cell lines. MC-16, a monoclinic crystal with P21/c space group, was further confirmed by X-ray and 2D-NMR. Results demonstrated that b5 was reacted with 7 equivalents NCS to given c5, and then MC-16 was obtained by the reaction of nitrile oxides derivatized from c5 with e1, passing intermediate state TS1. Bioactive results indicated that eight compounds (MC-2, MC-4, MC-5, MC-9, MC-10, MC-14, MC-19 and MC-20) exhibited weak to strong cytotoxicity against HepG2 cell lines, and their toxicity to Vero cells was much lower than that of Cisplatin (IC50 (HpeG2) = 8.44 & mu;M/ L, IC50 (Vero) = 28.63 & mu;M/ L, SI= 3.39). Among them, MC-14 (IC50 (HpeG2) = 12.85 & mu;M/ L, IC50 (Vero) = 144.32 & mu;M/ L, SI= 11.23) owned the strongest anti- HepG2 activity and obviously induced apoptosis under 48 & mu;M. Structure-relationship analysis displayed that substituent group R = Cl or Br was the key factors to enhance the anti-HepG2 activity. The docking results revealed that bioactive compounds can effectively interacted with protein (PDB ID: 6O5N).
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