Density Functional, Dielectric Studies and Anticancer Activity of (2e)-1-(3-Bromothiophen-2-yl)-3-(2, 3, 5-Trimethoxyphenyl) Prop-2-en-1-One

Abstract

In this work, the optimized structure parameters, and vibrational wavenumbers of (2E)-1-(3-Bromothiophen-2-yl)-3-(2, 3, 5-trimethoxyphenyl) prop-2-en-1-one (BTTP) molecule have been predicted by Density Functional Theory (DFT) method with B3LYP/6–311++G (d,p) basis set. The calculated vibrational wavenumbers have been compared with observed FT-IR (4000 − 400 cm⁻¹) and FT-Raman (3500 − 100 cm⁻¹) wavenumbers. The difference between the observed and the scaled wavenumber values of most of the fundamentals is very small. Using the aid of VEDA 4 software, the vibrational assignments were made using potential energy distributions. The calculated HOMO, LUMO energies and energy differences demonstrate that charge transfers take place within the molecule. The stability of the molecule arising from hyperconjugative interactions, and charge delocalization have been analyzed using natural bond orbitals (NBO) analysis. The results provide that charge in electron density (ED) in the bonding, and antibonding orbital and second order delocalization energies E⁽²⁾ confirms the occurrence of intramolecular charge transfer (ICT) within the molecule. Thermodynamic parameters such as entropy (S), enthalpy changes (ΔH) and heat capacity at constant pressure (C_p) are calculated in the temperature range from 100 to 700 K. The first hyperpolarizability (β), dipole moment (μ), and polarizability (α) values are being used to confirm the nonlinear optical behavior of the molecule. In addition, the dielectric properties explain the interactions between the sample and solvent at high frequencies. Finally, the compound is taken for the docking studies and molecular docking was performed against the potential target protein tankyrase and the results are compared with the drug Warfarin. The anticancer activity of BTTP confirms that it can be treated as antineoplastic against the two tested cell lines.