One-pot synthesis and molecular docking study of pyrazoline derivatives as an anticancer agent
Pyrazoline derivatives as an anticancer agent
DOI:
https://doi.org/10.46542/pe.2023.232.260265Keywords:
Anticancer, Molecular docking, One-pot synthesis, PyrazolineAbstract
Background: Pyrazoline is a series of heterocyclics with an N–N bond linkage, which is the determining factor in their biological activities, including anticancer.
Objectives: This research aims to synthesise pyrazoline derivative compounds with anticancer potential.
Method: 4-Metoxyacetophenon, halogen-substituted benzaldehyde, and phenylhydrazine were used to prepare pyrazoline derivatives (4a, b) under basic conditions using a microwave-assisted, one-pot, three-component reaction method. UV, FTIR, 1H-NMR, and HRMS spectrometers were used to confirm the molecular structure of pyrazolines (4a, b) using their UV, FTIR, 1H-NMR, and HRMS spectra. The anticancer activity of the compounds (4a, b) was evaluated using molecular docking studies to observe the receptor-ligand interaction of the compounds with the Estrogen Receptor Erα.
Result: The pyrazoline (4a, b) produced positive results, with approximately 40% yield. It can be used as an anticancer agent due to its binding free energy values of -9.74 and -9.29 respectively, and a receptor-ligan interaction.
Discussion and Conclusion: New pyrazolines (4a, b) have been successfully synthesised with good yields through the one-pot three-component reaction and have potential as anti-breast cancer agents because of their good affinity for the ERα evidenced by the negative binding free energy values and receptor-ligand interactions that are similar to natural ligand, 4OHT.
References
Ahmad, A., Husain, A., Khan, S. A., Mujeeb, M. & Bhandari, A. 2016. Synthesis, Antimicrobial and Antitubercular Activities of Some Novel Pyrazoline Derivatives Antimicrobial and Antitubercular Activities of Novel Pyrazoline Derivatives. Journal of Saudi Chemical Society, 20(5):577–84 https://doi.org/10.1016/j.jscs.2014.12.004
Ali, S., Rasool, M., Chaoudhry, H., Pushparaj, P. N., Jha, P., Hafiz, A., Mahfooz, M., Sami, G.A., Kamal, M.A., Bashir, S., Ali, A. & Jamal, M.S. (2016). Molecular Mechanisms and Mode of Tamoxifen Resistance in Breast Cancer. Bioinformation, 12(3):135-139 https://doi.org/10.6026/97320630012135
Constantinescu, T. & Claudiu N.L. (2021). Anticancer Activity of Natural and Synthetic Chalcones. International Journal of Molecular Sciences, 22(21) https://doi.org/10.3390/ijms222111306
Hawaiz, F.E., Hussein, A.J. & Samad, M.K. (2014). One-Pot Three Component Synthesis of Some New Azo-Pyrazoline Derivatives. European Journal of Chemistry. 5(2): 233–236 https://doi.org/10.5155/eurjchem.5.2.233-236.979
Kumar, L., Lal, K., Yadav, P., Kumar, A., & Paul, A.K. (2020). Synthesis, Characterization, α-Glucosidase Inhibition and Molecular Modeling Studies of Some Pyrazoline-1H-1,2,3-Triazole Hybrids. Journal of Molecular Structure, 1216 https://doi.org/10.1016/j.molstruc.2020.128253
Lumachi, F. (2015). Current Medical Treatment of Estrogen Receptor-Positive Breast Cancer. World Journal of Biological Chemistry, 6(3):231 http://dx.doi.org/10.4331/wjbc.v6.i3.231
Sharma, S., Kaur, S., Bansal, T. & Gaba, J. (2014). Review on Synthesis of Bioactive Pyrazoline Derivatives. Chemical Science Transactions, 3(3):861-875. https://doi.org/10.7598/cst2014.796
Sakthinathan, S.P., Vanangamudi, G. & Thirunarayanan, G. (2012). Synthesis, Spectral Studies and Antimicrobial Activities of Some 2-Naphthyl Pyrazoline Derivatives. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 95:693–700 https://doi.org/10.1016/j.saa.2012.04.082
Sun, Y.S., Zhao, Z., Yang, Z.N., Xu, F., Lu, H.J., Zhu, Z.Y., Shi, W., Jiang, J., Yao, P.P. & Zhu, H. P. (2017). Risk Factors and Preventions of Breast Cancer. International Journal of Biological Sciences, 13(11):1387–97. https://doi.org/10.7150/ijbs.21635
Zamri, A., Teruna, H.Y. & Ikhtiarudin, I. (2016). The Influence of Power Variation on Selectivity of Synthesis Reaction of 2 ’-hydroxychalcone Analogue Under Microwave Irradiation. Molekul, 11:299–307 http://dx.doi.org/10.20884/1.jm.2016.11.2.220
