Photophysical and In Vitro-In Silico Studies on Newly Synthesized Ethyl 3-((3-Methyl-1-phenyl-1H-pyrazol-5-yl)oxy)-2-methyleneheptanoate

In the present work, the aryl-substituted pyrazolone derivative ethyl 3-((3-methyl-1-phenyl-1H-pyrazol-5-yl)oxy)-2-methyleneheptanoate (ETT) has been synthesized by the reaction of Baylis-Hillman acetate with pyrazolones and screened for their in vitro antifungal, antibacterial, and antioxidant properties. The molecule shows good in vitro antifungal and antibacterial activities due to the presence of pentane, which enhances the absorption rate by its increased lipid solubility and improves the pharmacological activity. It is also evident from the results obtained from structure-activity relationship (SAR) studies. In silico studies were conducted on the synthesized molecule, examining its interactions with DNA Gyrase, Lanosterol14 alpha demethylase, and KEAP1-NRF2 proteins. The results revealed strong binding interactions at specific sites. Further, the photophysical properties of synthesized compounds were theoretically estimated using the ab-intio technique. The ground state optimization, dipole moment, and HOMO–LUMO energy levels are calculated using the DFT-B3LYP-6-31G(d) basis set. Using the theoretically estimated HOMO–LUMO value, global chemical reactivity descriptor parameters are estimated, and the result shows the synthesised molecule has a highly electronegative and electrophilic index. NBO analysis proved the presence of intermolecular ON^.H hydrogen bonds caused by the interaction of the lone pair of oxygen with the anti-bonding orbital. The results suggest that pentane-substituted pyrazolone derivatives show good photophysical and biological applications.