A novel coumarin-triazole-thiophene hybrid: synthesis, characterization, ADMET prediction, molecular docking and molecular dynamics studies with a series of SARS-CoV-2 proteins.

Synthesis, characterization and theoretical studies of a novel coumarin-triazole-thiophene hybrid 4-(((4-ethyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-3-yl)thio)methyl)-6,7-dimethyl-2H-chromen-2-one (1), which was fabricated from 4-ethyl-5-(thiophen-2-yl)-4H-1,2,4-triazole-3-thiol and 4-(chloromethyl)-6,7-dimethyl-2H-chromen-2-one, are reported. The resulting compound was characterized by microanalysis, IR, 1H, and 13C APT NMR spectroscopy. The DFT calculations examined the structure and electronic properties of 1 in gas phase. Its reactivity descriptors and molecular electrostatic potential revealed the reactivity and the reactive centers of 1. ADMET properties of 1 were evaluated using the respective online tools. It was established that 1 exhibit positive gastrointestinal absorption properties and negative human blood-brain barrier penetration. The Toxicity Model Report revealed that 1 belongs to toxicity class 4. Molecular docking was additionally applied to study the interaction of 1 with some SARS-CoV-2 proteins. It was established that the title compound is active against all the applied proteins with the most efficient interaction with Papain-like protease (PLpro). The interaction of 1 with the applied proteins was also studied using molecular dynamics simulations. Graphical abstract: A novel coumarin-triazole-thiophene hybrid 4-(((4-ethyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-3-yl)thio)methyl)-6,7-dimethyl-2H-chromen-2-one (1) is reported. The structure and electronic properties of 1 were examined by the DFT calculations. ADMET properties of 1 were also evaluated. Molecular docking and molecular dynamics simulations were applied to study interactions of 1 with a series of the SARS-CoV-2 proteins. Supplementary Information: The online version contains supplementary material available at 10.1007/s12039-022-02127-0.

Synthesis of Ribose - Oleic Acid Esters in the Presence- and Absence of Candida antarctica Lipase B.

D-ribose-oleic acid esters were produced with or without a biocatalyst, using in the same organic media, dimethyl sulfoxide (DMSO): tert-butanol (TBU) or 2-methyl-2-butanol (2M2B). The yield of the ester product was above 90% in both of the reactions. The biocatalyst used was lipase B of Candida antarctica. Molecular characterization was performed by using all the analytical methods available: IR, 1H-NMR and 13C-NMR, HSQC, and ESI-MS.

D-Glucose-fatty Acid Ester Synthesis with or without a Biocatalyst in the Same Organic Media.

Esterification of D-glucose with oleic- and palmitic acids were carried out in the absence and presence of a biocatalyst, Candida antarctica lipase. The reaction medium was a mixture of dimethyl sulphoxide and tert-butanol (1:4, v/v). The reaction products were analysed by FTIR, 1H-NMR and 13C-NMR, HSQC, and by ESI-MS. Results indicated that the ester products formed were 6-O-glucose oleate and 6-O-glucose palmitate both in the absence and in the presence of the biocatalyst, with yields above 90%.