Synthesis, in vitro and in silico antitumor evaluation of 3-(2,6-dichlorophenyl)-1,5-diphenylpentane-1,5‑dione: Structure, spectroscopic, RDG, Hirshfeld and DFT based analyses.

• A new bischalcone was synthesized and characterized by single crystal X-ray diffraction. • Intermolecular interactions are studied using Hirshfeld surface analysis. • In vitro and in silico antitumor evaluation was assessed against A549 cancer cell line. • Bischalcone compound has shown significant antitumor activity. • Good antibacterial and antifungal activity have shown by bischalcone. New bischalcone derivative 3-(2,6-dichlorophenyl)-1,5-diphenylpentane-1,5‑dione (C 23 H 18 Cl 2 O 2) has been efficiently synthesized and the solid state formation of the grown crystals was characterized by X-ray crystallographic diffraction (XRD)analysis at 296 K. The single crystal XRD results show that the title compound belongs to triclinic system with unit cell dimensions, a = 9.4104 (12) (Å), b = 10.2951(13) (Å), c = 10.9411(15) (Å) and V = 980.9(Å3). The key contributor intermolecular interactions C‒O···H/H···O‒C were explored by Hirshfeld surface analysis. The active functional group interpretations have been carried using FT-IR and FT-Raman spectroscopies with the assistance of energy distributions. Density functional theory (DFT) calculations of the synthesized compound carried out for better understanding of molecular futures. Hyperconjugative interactions present in the molecule were also quantified using natural bond orbitals (NBO). Reactivity and stability of the title molecule assessed utilizing global reactivity descriptors. The condensed Fukui functions explored the available electrophile and nucleophile regions in the form of local based descriptors. The reduced density gradient (RDG) isosurfaces reveals the dominance of non-bonded interactions of the title compound. MTT assay revealed that the title compound had potentiate antitumor activity against human lung cancer A549 cells with 40.71 µg/mL IC 50 value. Moreover the capability of the compound to be interconnected within the key amino acids of lung cancer receptor binding sites was detected by molecular docking. Antibacterial and antifungal efficacy of the title compound studied using Kirby-Bauer disc diffusion technique. [Display omitted] [ABSTRACT FROM AUTHOR]