Quantum Chemical and Biological Properties of Coumarin Derivative Compound

Abstract

This work presents the characterization of 8-t-buthyl-4-methyl-2H- chromen 2-one by quantum chemical calculations and spectral techniques. The molecular geometry, vibrational frequencies and gauge including atomic orbital (GIAO) 1H and 13C NMR chemical shift values of title compound in the ground state have been calculated using the density functional method (B3LYP) with the 6-31G(d) basis set. The theoretical vibrational frequencies and chemical shift values show good agreement with experimental values. In addition, DFT calculations of molecular electrostatic potentials and frontier molecular orbitals of the title were carried out at the B3LYP/6-31G(d) level of theory. The title compound was screened for antibacterial, antifungal and antioxidant activities.

Keywords

• Coumarin
• Theoretical
• Biological effects

References

1. Rashid, F., Rahim, M., Taha, M., Arshad, H., Ullah, T., Mahmood, M. Ali, M.,2016. Synthesis of 2-Acylated and Sulfonated 4-Hydroxycoumarins: in Vitro Urease Inhibition and Molecular Docking Studies. Bioorganic Chemistry 66, 111-116. doi: 10.1016/j.bioorg.2016.04.005.
2. Cao, Y., Liu, W., Yan, C., Wang, P., Bai, T., Wang, M. Tang, X., Wang, Z., Yang, B., Ma et. al.,2016. Design, Synthesis, and Evaluation of in Vitro and in Vivo Anticancer Activity of 4-Substituted Coumarins: A Novel Class of Potent Tubulin Polymerization Inhibitors. Journal of Medicinal Chemistry 59, 12: 5721-5729. doi: 10.1021/acs.jmedchem.6b00158.
3. Manjinder, K., Swarandeep, S., Sonali, B., Yogita, B., Gulshan,.2015. Coumarin: A Promising Scaffold for Anticancer Agents, Anti-Cancer Agents in Medicinal Chemistry 15, 1032-1048. doi: 10.2174/1871520615666150101125503.
4. Emami, S., and Dadashpour, S., 2015. Current Developments of Coumarin-Based Anti-Cancer Agents in Medicinal Chemistry. European Journal of Medicinal Chemistry 102: 611-630. doi: 10.1016/j.ejmech.2015.08.033.
5. Patel, P., Kumari, N., Patel, B., 2017.Synthesis and Biological Evaluation of Coumarin Based Isoxazoles, Pyrimidinthiones and Pyrimidin-2-Ones. Arabian Journal of Chemistry 10, 3990-4001. doi: 10.1016/j.arabjc.2014.06.010.
6. Niu, W., Wang, J.,Li, Y., Lei, Y., Zhao, W., Yang, C., Zhao, B., Lin, S., Song, S., Wang., 2017. A Novel Structural Class of Coumarin-Chalcone Fibrates as Pparalpha/Gamma Agonists with Potent Antioxidant Activities: Design, Synthesis, Biological Evaluation and Molecular Docking Studies. European Journal of Medicinal Chemistry 38, 212-220. doi: 10.1016/j.ejmech.2017.06.033.
7. Srivastava, V.K., Vyas, B., Variya, P., Patel, G., Qureshi, M., Ghate, K.,2016. Synthesis, Anti-Inflammatory, Analgesic, 5-Lipoxygenase (5-LOX) Inhibition Activities, and Molecular Docking Study of 7-Substituted Coumarin Derivatives. Bioorganic Chemistry 67, 130-138. doi:10.1016/j.bioorg.2016.06.004.
8. Luo, J.G., Sun, J.W. Chan, L., Yang, S.H., 2011.Anticancer Effects of Imperator in Isolated from Angelica Dahurica: Induction of Apoptosis in Hepg2 Cells Through Both Death-Receptor-and Mitochondriamediated Pathways. Chemotherapy 57: 449-459. doi:10.1159/000331641.

9. Hoult, J.R., and Paya, M., 1996.Pharmacological and Biochemical Actions of Simple Coumarins: Natural Products with Therapeutic Potential. General Pharmacology 27: 713-722. doi:10.1016/0306-3623(95)02112-4.
10. Maleki, A. R., Bahrami, H., Sadeghian, M. M., Matin, R., 2020. Discovering the Structure–Activity Relationships of Different O-Prenylated Coumarin Derivatives as Effective Anticancer Agents in Human Cervical Cancer Cells. Toxicology in Vitro 63: 104745. doi: 10.1016/j.tiv.2019.104745.
11. Ipek, B. O., Sucu, S., Gul, C., Yolacan, M. Guzel, M.,2023. Synthesis of Novel Hybrid Lonidamine-Coumarin Derivatives and Their Anticancer Activities. Journal of Molecular Structure 1281, 135114. doi.org/10.1016/j.molstruc.2023.135114.
12. Holiyachi, S. L., Shastri, B. M., Chougala, N. S., Naik, V., Pawar, L. A., Shastri, S. D., Joshi, V. A., Sunagar, a.,2021. Design and Synthesis of New Series of Dipyrromethane-Coumarin and Porphyrin-Coumarin Derivatives: Excellent Anticancer Agents. Journal of Molecular Structure 1237, 130424. doi.org/10.1016/j.molstruc.2021.130424
13. Schiegel,H.,1982. Comput. Chem. 214-218.
14. Dennington R., Keith, T., Millam,J.,2007. Gauss View, Version 4.1.2, Semichem, inc, Shawnee Mission.
15. Cossi,M., Rega,N.,Scalmani,G., Barone.V., 2003. J. Comput. Chem. 24,669-681.
16. Tomasi,J.,Mennucci,B.,Cammi,R., 2005 Chem. Rev. 105, 2999-3093