Computational Characterization of Perezone, Isoperezone and their Sulfur‐Derivatives: Anti‐inflammatory Activity.

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.

Can (S)‐Stereoisomers of Perezone and Its Derivatives Show Similar Activity to Its (R)‐Stereoisomers? A Computational Characterization and Docking Study

“…In this sense, for 1 a-d a medium band for C3À O3 was detected at a range 1231.22 to 1235.57 cm À 1 . These values match with the theoretical (R)stereoisomer data, [5] and at 1231.47-1248.89 cm À 1 was observed a band for C3À O3.…”

“…[a] Most stable stereoisomer between analogs. [b] See reference [5] an appropriated analysis of the vibrational modes; this in addition to the corresponding shielding or deshielding effects, δ ppm.…”

“…Therefore, the analyses are centered on selected vibrational modes: OÀ H, C1=O1, and C4=O4 for all molecules, in addition to C6À H6, C3À O3 or C3À H3, and C6À O6 for perezone and isoperezone respectively, and C6-S for perezone sulfurs and C3-S for isoperezone sulfurs. The harmonic frequencies, with scaling factor (0.9679) [5,9,[15][16][17] of selected modes were compared to the available experimental data. Some selected calculated harmonic frequencies and the descriptions concerning the assignment are listed in Table 2 and were compared with the experimental and (R)-stereoisomer data.…”

“…[6][7][8] In this sense, the base set, 6-311 + + G(d,p), employed to evaluate the vibrational analysis has resulted a very good approximation for organic molecules. [5,[9][10] Considering our actual research program, we are interested in the spectroscopical characterization (IR and NMR), [5,[11][12] in addition to the study of pharmacologically interesting organic compounds, both natural and synthetic, using appropriately computational studies. Hence, the goal of this research, implicates the convenience to produce, a set of hypothetic molecules, 1 and 3, and their corresponding sulfur-derivatives (a-d), evaluating their molecular properties at a theoretical level, comparing the corresponding results with the known (R)stereoisomers using DFT-methodology at B3LYP/6-311 + + G-(d,p) level.…”

A Theoretical Study of the Adsorption Process of B-aflatoxins Using Pyracantha koidzumii (Hayata) Rehder Biomasses

“…Recently, computational theoretical chemistry methods have been used in property predictions, drug designs, and the study of molecular interactions in a wide variety of compounds [14][15][16][17]. In this context, a feasible strategy is the use of quantum chemical calculations to accurately explain the aflatoxin-biosorbent interactions and the main functional groups responsible in the biosorption process.…”