Molecular docking, expounding the chemo-, regio-selectivity, and the mechanism of [3 + 2] cycloloaddition reaction between nitrile-imine and (thio)-chalcone.

Autor: Ryachi, Kamal, idrissi, Mohammed El, Mohammad-Salim, Haydar, Bahkali, Ali H., de Julián-Ortiz, Jesús Vicente, Zeroual, Abdellah, Wang, Shifa, Wong, Ling Shing, Syed, Asad, Tounsi, Abdessamad
Zdroj: Chemical Monthly / Monatshefte für Chemie; Jul2024, Vol. 155 Issue 7, p697-707, 11p
Abstrakt: The study explores the application of molecular electron density theory, focusing on the [2 + 3] cycloaddition mechanisms between nitrile-imine and chalcone or thiochalcone. Density Functional Theory (DFT) calculations employing the B3LYP/6–311(d,p) methodology are utilized to determine activation and reaction energies, as well as reactivity indices. Through investigation of conceptual DFT indices, nitrile-imine is identified as a nucleophile, while chalcone and thiochalcone act as electrophiles in the reaction. The reactions exhibit both chemo- and regiospecifics, as confirmed by Parr functions, Electron Localization Function (ELF) survey, and energetic analysis, consistent with experimental results. ELF analysis suggests a two-phase mechanism for these [2 + 3] cycloadditions. Furthermore, docking studies on the resultant products reveal enhanced interaction energies with proteins due to the presence of oxygen and sulfur atoms, in their interaction with the crystal structure of COVID-19 main protease (PDB ID: 6LU7) and paves a ways for manufacturing innovation. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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