Synthesis, structure determination, molecular interaction analysis, molecular docking studies, and anticancer activity investigation of a chalcone derivative: (2E)-2-[(2,4-dimethoxyphenyl)methylidene]-3,4 dihydronaphthalen-1(2H)-one

• Main Authors: Angeline Shirmila, D., Reuben Jonathan, D., Krishna Priya, M., Laavanya, K., Hemalatha, J., Usha, G.
• Format: Conference Proceeding
• Language: English
• Subjects: Anticancer activity; Chalcone; Crystal structure; Hirshfeld surfaces; In vitro and in silico analysis
• ISSN: 2214-7853; 2214-7853
• DOI: 10.1016/j.matpr.2022.04.479

•A new chalcone derivative DMMD was synthesized using Claisen-Schmidt condensation reaction.•1H NMR and 13C NMR studies were used to characterize DMMD.•Hirshfeld surfaces and energy frameworks analysis was performed to visualize the non-bonded interactions.•Cytotoxicity and anticancer activity of DMMD was analysed using MTT assay and drug-likeness was examined using in-silico pharmacokinetic analysis.•Molecular Docking studies of DMMD with 1M17 protein showed good binding affinity with amino acid residues Met 769 and Lys 721. A new chalcone derivative was synthesized using Claisen-Schmidt condensation reaction and its structure was determined using single-crystal X-Ray Diffraction (XRD) technique. Hirshfeld surfaces were generated to visualize and quantify short contacts, regions of varying potentials, and C-H…π and π…π stacking interactions. 2D fingerprint plots were analyzed, in which the contribution due to H…H contact to the total Hirshfeld surface was found to be the most significant with 54.1%. The cytotoxicity assay proved that the compound is non-toxic to the normal Vero cell line. The anticancer activity studies affirm the potentiality of the compound to inhibit the growth of MCF-7 cell lines with 52.46% of cell viability at IC50 value of 7.8 μg/mL. Molecular docking simulation revealed that the ligand fits well at the active site of the target protein 1M17. In-silico pharmacokinetic studies reveal that the compound is orally active and demonstrates a good pharmacokinetic profile.