Abstract
A new series of C4-N,N-dialkylaniline-substituted 4-aryl-4H-chromenes were synthesized, and their anti-proliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549), and cervical cancer (HeLa). The best among them, the 4-aryl-4H-chromene with C4-1-phenylpiperidine substitution was selected for further structure activity relationship (SAR) studies. Among the derivatives, N,6-dimethyl-3-nitro-4-(4-(piperidine-1-yl)phenyl)-4H-chromene-2-amine 3k showed most potent cytotoxic activity against all three cancer cell lines. Toxicity studies revealed that the 4-aryl-4H-chromenes specifically target the cancer cell lines. Molecular docking studies of this compound revealed its efficient interaction with the active site of αβ-tubulin protein.
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Acknowledgments
AP thanks Pondicherry University for fellowship. JM (09/559/(0076)/2011/EMR-1, dated 30-3-3011) and MK (09/559/(0100)/2013/EMR-I, dated 16-3-2013) thank the Council of Scientific and Industrial Research (CSIR) for Senior Research Fellowship (SRF). Authors thank the Centre for Bioinformatics (Funded by Department of Biotechnology and Department of Information Technology, New Delhi, India) and Central Instrumentation Facility, Pondicherry University, for providing the computational facilities and spectroscopic instruments to carry out the research work. HSPR thanks the UGC for the Special Assistance Program (SAP) and the Department of Science and Technology (DST) for the Fund for Improvement of S&T Infrastructure in Higher Educational Institutions (FIST). Authors also thank ‘‘Interdisciplinary Programme of Life Sciences for Advanced Research and Education’’ (IPLS) funded by DBT, India, for support.
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Parthiban, A., Kumaravel, M., Muthukumaran, J. et al. Synthesis, in vitro and in silico anti-proliferative activity of 4-aryl-4H-chromene derivatives. Med Chem Res 25, 1308–1315 (2016). https://doi.org/10.1007/s00044-016-1569-z
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DOI: https://doi.org/10.1007/s00044-016-1569-z