Structural, spectroscopic and quantum chemical analysis of an exocyclic extended double-bonded chalcone single crystal, with pharmaceutical scanning for breast cancer using MCF-7 cell line and EGFR domain target

Abstract

A chalcone derivative, (2E)-2-[(2E)-3-(4-methoxyphenyl)prop‑2-en-1-ylidene]-3,4-dihydronaphthalen-1(2H)-one [MPDN] was synthesized by slow evaporation method using Claisen-Schmidt condensation reaction. Single-crystal X-Ray Diffraction (SXRD) analysis was carried out to determine the structure, inter and intramolecular interactions, and conformation of the title molecule. The SXRD study shows that the compound crystallizes in a monoclinic crystal system with a space group P 21/c with lattice parameters; a = 15.178 (2), b = 7.369 (9), c = 14.322 (19) Å and β = 108.113 (4)° and V = 1522.6 (3)Å3. The molecular interactions in the structure were studied using Hirshfeld surface analysis. The Hirshfeld surface mapped over dnorm, electrostatic potential, shape index, curvedness, and energy framework were also analyzed, which provide valuable information about all kinds of available molecular interactions. The compound was further studied theoretically for the molecular structure, crystal geometry, and chemical reactivity descriptors via Density Functional Theory (DFT) calculations. Charge transfer across the energy levels (NBO) and the charge density over the atoms (Mulliken) were also analyzed. Vibration frequencies (stretching/bending) were analyzed using both experimental and theoretical spectra. The Ultra Violet-Visible (UV–Vis) spectrum shows π-π* transitions with a band gap 2.9 eV (Tauc-plot). Thermo-gravimetric and Differential Thermal Analysis (TGA/DTA) thermograms were studied to note the thermal behavior of MPDN. Cytotoxicity on (VERO) and in-vitro investigation (MCF-7) cell lines was done to quantify the material's efficacy as an anticancer agent. The optimized molecule was also docked with a protein target (PDB ID: 1M17) to study its pharmaceutical viability to inhibit cancer proliferation using AutoDock 4.2.6 software and was found to be a potential anticancer agent.