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

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 IC 50 6.50 µM when exposed to the cell line for 24 hours compared to the reference Gefitinib anticancer drug.

Synthesis, Characterization, Anti-Inflammatory, and Antimicrobial Evaluation of New 2-Pyrazolines Derivatives Derived from Guaiacol

“…The polyphenolic compound chalcone (1,3-diphenyl-2-propen-1-one) with the general formula (Ar-C=O-CH=CH-Ar) belongs to the flavonoids family (1). The general formula of chalcone C15H12O has two stereochemistry, cis and trans, but trans (-1,3-diphenyl-2-propene-1-one) is much more reactive than cis isomer (1,3-diphenyl-2-propene-1-one) as shown in "Figure . 1" (2) . Figure 1.…”