No abstract

Using DFT and in silico methods a theoretical study, to verify the spectroscopically characterization, this in addition to determine the anti‐inflammatory activity of a set of eight sulfur derivatives of perezone and isoperezone was performed. In this sense, conformational studies for the target sulfurs were carried out, in order to obtain the corresponding minimum energy structures. Also, the vibrational frequencies analysis, the magnitude of 1H NMR and 13C NMR spectra for perezone, isoperezone, and its sulfur‐derivatives, obtained by the DFT/B3LYP/6‐311++G(d,p) method correlated satisfactorily with the experimental data. Moreover, the calculation of physicochemical properties, and the prediction of the anti‐inflammatory activity, employing both PASS predictor and docking studies towards COX‐2 for the target compounds, showed that Benzy perezone is a good candidate as a therapeutic agent; finally, the anti‐inflammatory activity of Benzy perezone was evaluated in vivo, showing a similar naproxen activity.

A green approach to produce the indolyl derivatives from four natural quinones (perezone, isoperezone, menadione, and plumbagin) was performed; in this regard, a comparative study was accomplished among the typical mantle heating and three nonconventional activating modes of reaction (microwave, near-infrared, and high speed ball milling or tribochemical), under solventless conditions and using bentonitic clay as a catalyst. In addition, the tribochemical production of isoperezone from perezone is also commented on. It is also worth noting that the cytotoxicity of the synthesized indolylquinones in human breast cancer cell was tested by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, with the 3-indolylisoperezone being the most active. The structural attribution of the target molecules was performed by typical spectroscopic procedures; moreover, the experimental and computed1H and13C NMR chemical shifts data, with previous acquisition of the corresponding minimum energetic structures, were in good agreement.