Fluorinated-antioxidant derivatives with improved pharmacological activity: a theoretical study.

It has become obvious that fluorinated drugs have a significant role in medicinal applications. In this study, the fluorination of ferulic acid (FA) antioxidant was investigated using density functional theory calculations. We have explored the most important chemical properties of FA that affects the pharmacological activity of antioxidant. We found that the intramolecular hydrogen bonding and charge transfers of the FA were influenced by fluorine substitution. Our results also reveal that the fluorination altered the stability, solubility and molecular polarity of the FA. Moreover, our results show that the electronic spectra of fluorinated derivatives of FA exhibit the red and blue shifts toward higher and lower wavelengths, respectively, compared to the original FA. Our calculations show that the free energy transfer of fluorinated derivatives of the FA in water was negative that it meant that the designed molecules dissolving in aqueous phase occurred simultaneously. We also found that the fluorination can increase the first hyperpolarizability of the FA. Our results present an efficient strategy to improve the nonlinear optical responses of the antioxidants. Consequently, the results of present study show that the fluorination of FA could be considered as a promising strategy to design useful drugs with better pharmacological properties.[Formula: see text]Fluorination is an effective strategy to improve pharmacological activity of frulic acid antioxidant.Communicated by Ramaswamy H. Sarma.