Abstract
A set of 2-amino-4-aryl-4H-pyrano[3,2-h]quinoline-3-carbonitrile derivatives were prepared via a one-pot, three-component condensation reaction between the substituted hydroxyquinoline derivatives, some aryl and/or hetaryl aldehydes, and malononitrile in an ethanol/piperidine solution in a microwave irradiation environment. The structure of the prepared compounds was instituted on the foundations of their spectral data: IR, 1H NMR, 13C NMR, and MS. Four human cancer cell lines, MCF-7, HCT-116, HepG-2, and A549 were utilized to evaluate the antiproliferative properties of the target compounds in comparison to the positive controls, Vinblastine and Colchicine using the MTT viability assay. The cell cycle arrest behavior, detected by propidium iodide as well as the apoptosis induction, which was monitored by the flow cytometer, using the Annexin V-FITC kits, was investigated. The results illustrated that the potent cytotoxic compounds induce cell cycle arrest at the G2/M phases and trigger apoptosis in the different tested cancer cells. Finally, the structure−activity relationship (SAR) study showcases the substitution of some specific groups at the 4-, 6-, and 9-positions in the prepared 2-amino-4H-pyrano[3,2-h]quinoline derivatives, which indicates that the lipophilicity manipulates the ability of these moieties against the diverse cell lines.
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Acknowledgements
The authors extend their appreciation to the Deanship of Science Research at King Khalid University for funding this work through General Research Project under Grant Number (G.R.P-168-39). In addition, the authors deeply thank the Regional Center for Mycology & Biotechnology (RCMP), Al-Azhar University, Cairo, Egypt, for carrying out the antitumor study and also, Mr. Ali Y. A. Alshahrani for drawing the 1H NMR and 13C NMR spectra.
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Fouda, A.M., Youssef, A.M.S., Afifi, T.H. et al. Cell cycle arrest and induction of apoptosis of newly synthesized pyranoquinoline derivatives under microwave irradiation. Med Chem Res 28, 668–680 (2019). https://doi.org/10.1007/s00044-019-02325-5
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DOI: https://doi.org/10.1007/s00044-019-02325-5