Design, synthesis, characterization, and cytotoxicity activity evaluation of mono-chalcones and new pyrazolines derivatives

Kassim Ali Salum; Mohammad Murwih Alidmat; Melati Khairulddean; Nik Nur Syazni Nik Mohammad Kamal; Musthahimah Muhammad

doi:10.7324/JAPS.2020.10803

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Abstract

The development of resistance and side effects of chemotherapeutic drugs are common obstacles in the treatment of cancer. With the expansion of health problems nowadays, there is a need to continuously develop new drugs that are more efficient in targeting tumor cells and safe to normal cells. This study designed a series of new chalcones and pyrazoline derivatives based on their binding energy from the molecular docking study. The synthesis involved Claisen–Schmidt condensation to form two chalcones, 1 and 2, which are then cyclized at room temperature to form eight new pyrazoline derivatives, 3–10. A one-pot reaction of acetophenone, 2-ethoxybenzaldehyde, and hydrazide derivatives (thiosemicarbazide and phenyl hydrazide) under reflux formed two new pyrazoline derivatives, 11 and 12, without the isolation of chalcones. All the synthesized chalcones and pyrazolines were characterized using the Fourier transform infrared spectroscopy–attenuated total reflectance and nuclear magnetic resonance (1D and 2D). The cytotoxicity activity of the chalcones and new pyrazoline compounds were investigated against breast cancer cell lines (MCF-7 and MD-MB-231) and normal breast cell lines (MCF-10A). The results show that only compound 7 showed the minimum inhibition against MCF-7 with IC₅₀6.50 μM when exposed to the cell line for 24 hours compared to the reference Gefitinib anticancer drug.

Keyword: Chalcone pyrazoline claisen–schmidt condensation acetophenone.

Citation:

Salum KA, Murwih M, Khairuddean M, Kamal NNSNM, Muhammad M. Design, synthesis, characterization, and cytotoxicity activity evaluation of mono-chalcones and new pyrazolines derivatives. J Appl Pharm Sci, 2020; 10(08):020-036.

Copyright: © The Author(s). This is an open-access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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