ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Spectroscopic, quantum computational, molecular docking and biological parameters of 4-phenylbutyrophenone: a neuroleptic agent

B. R. Raajaraman, N. R. Sheela, and S. Muthu

Department of Applied Physics, Sri Venkateswara College of Engineering, Sriperumbudur, India

E-mail: mutgee@gmail.com

Received: 14 October 2020  Accepted: 18 March 2021

Abstract:

In this work, density functional theory and vibrational spectroscopic studies are carried out to elucidate the structure, physiochemical parameters and biological behaviors of 4-phenylbutyrophenone. By using energy minimization, the optimized structure of 4-phenylbutyrophenone (4PBP) is obtained. The functional group present in the compound and its properties are obtained by FT-IR, FT-Raman and NMR methods, and it is compared with simulated scaled values along with assignments by potential energy distribution. The inter- and intramolecular charge transfer and stability of the molecule are obtained by natural bond orbital analysis. The reactive areas of the molecule are studied quantitatively and qualitatively by Fukui function analysis and molecular electrostatic potential diagram, respectively. By using frontier molecular orbital theory, the highest occupied molecular orbital, lowest unoccupied molecular orbital and other various parameters are calculated and compared with the known antipsychotic drug melperone. The electronic transition is obtained by experimental UV–Vis spectrum, and it is compared with the time-dependent DFT method with various solvents. The effect of temperature on the molecule is discussed to know the thermal stability of the molecule. The drug-likeness values of 4PBP are compared with known human drugs to confirm the same neuroleptic activities, and it confirms the drug nature of 4PBP. In addition, comparative molecular docking was analyzed with this ligand and melperone (an a typical antipsychotic) with the suitable target protein. Lipophilicity studies compared with other drugs show that this has good transport well inside the human lipid system. Molecular docking supports the neurological activity of the compound with a low binding energy value of −7.55 kcal/mol to bound easily without additional energy with the target proteins confirms 4PBP is a good neuroleptics potential candidate.

Keywords: Density Functional Theory; Natural Bond Orbital; Molecular Electrostatic Potential; Molecular Docking

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01617-8

Chemical Papers 75 (8) 3931–3948 (2021)