Synthesis, single crystal, in-silico and in-vitro assessment of the thiazolidinones

Aisha, Muhammad Asam Raza, Umme Farwa, Umer Rashid, Jan K.Maurin, Armand Budzianowski

https://doi.org/10.1016/j.molstruc.2022.132384

Highlights

• Three Thiazolidinone were prepared and characterized using FTIR, NMR and XRD techniques.
• In-Vitro enzyme inhibition assessments were checked in order to explore their biological importance.
• DFT and Docking studies were used to compare experimental and theoretical parameters.

Abstract

This project was aimed to check the enzyme inhibition potential of the synthesized thiazolidinones. The target compounds (1–3) were prepared according to reported method and characterized with FTIR and single-crystal X-Ray Diffraction techniques. The compounds were also evaluated theoretically carrying out their docking and DFT studies. Enzyme inhibition studies were carried out spectrophotometrically via in vitro model, which showed that compounds may be useful in therapeutic treatments. Compound 2 showed the highest inhibition against AChE (67.3%), BChE (78.2%) and alpha-glucosidase (86.4%) as compared to compound 1 and compound 3 which showed AChE (53.8%) and (59.5%), BChE (76.2%) and (62.8) α-glucosidase (79.4%) and (86.1%) inhibition, respectively. Docking results of the synthesized compounds were also in favor of experimental work as they exhibited so many interactions with different amino acids residues located on the active sites of the target enzymes. The compounds were optimized with Gaussian 9 using 6–31G(d,p) basis set. In Silico ADMET study of the compounds exhibited various therapeutic properties, which depicted that they are quite similar to the drug like candidates.

    Keywords: Thiazolidinones, ADMET, Docking study, Enzyme inhibition, XRD analysis

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