Synthesis, characterization, and anti-cancer activity of chalcone derivatives as-potent anaplastic lymphoma kinase inhibitors

• Published in: Structural chemistry 2021-08, Vol.32 (4), p.1597-1609
• Main Authors: Lakshmanan, Sivalingam, Govindaraj, Dharman, Mahalakshmi, K., Thirumurugan, K., Ramalakshmi, N., Antony, S. Arul
• Format: Article
• Language: English
• Subjects: Amino acids; Anticancer properties; Binding; Chemistry; Chemistry and Materials Science; Computer Applications in Chemistry; Doppler effect; Electron density; Emission analysis; Emission spectra; Free energy; Hydrogen bonding; Kinases; Morphology; NMR; Nuclear magnetic resonance; Original Research; Photoluminescence; Physical Chemistry; Receptors; Red shift; Solvents; Synthesis; Theoretical and Computational Chemistry; Toxicity
• ISSN: 1040-0400; 1572-9001
• DOI: 10.1007/s11224-020-01707-5

Chalcone derivatives ( 7a–k ) have been synthesized and characterized by 1 H-NMR, 13 C-NMR, mass, and elemental analysis. The synthesized compounds 7a, 7d , and 7g have been examined and it is confirmed that the most promising cytotoxicity and also cell morphology analysis exhibited good apoptotic activity against lung cancer A549 cell. The free energy binding of compound 7d exhibits − 8.96 kcal/mol with five hydrogen bonding Asn1254, Arg1253, Asp1249, and Gly1123 amino acids of ALK receptors. The LUMO of the electron density present in α, β-double bond and influence the anticancer activity. The Mulliken atomic charges and MEPs are scrutinizing the ligand interaction with the amino acid binding of ALK receptors. UV-visible and photoluminescence spectra showed that the properties of chalcone derivatives have a significant effect on the visible absorption and emission maxima (531–535 nm) red shift in the emission spectra which also systematically investigated electrochemical in various solvents with increasing solvent polarity.