Dedicated with great respect to Dr. Vijay Nair on the occasion of his 75 th birthday One of the most straightforward methods for the synthesis of disubstituted alkynes is the transition metal catalyzed Sonogashira-type cross-coupling reactions. Herein we report a detailed study of our recent research on the first Zn-catalyzed protocol for C(sp 2 )-C(sp) cross-coupling reaction of aryl iodides with terminal alkynes. A wide range of functional groups were tolerated in the reaction and both functionally and structurally diverse diaryl acetylenes were prepared efficiently using this protocol. The reaction mechanism for the Zn-catalyzed Sonogashira-type coupling reaction was investigated by means of density functional theory (DFT) methods on a model system. The calculations were performed using hybrid Becke Perdew Functional (BPV86) in conjugation with LANL-2DZ basis set and found that the reaction pathway involves oxidative addition and reductive elimination mechanism.
The global spread of the COVID-19 pandemic caused by the etiological agent, severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2), triggered researchers to identify and develop novel antiviral therapeutics. Herein, we report a new molecule 2-hydroxy-1,2-diphenylethanone N(4)-methyl-N(4)-phenyl thiosemicarbazone (BMPTSC), as a potential inhibitor of SARS-CoV-2. BMPTSC was synthesized, characterized by IR and NMR studies, and the structural parameters were analyzed computationally by B3LYP/cc-pVDZ method. Molecular docking studies were performed to get insights into the energetics and compatibility of BMPTSC against various SARS-CoV-2 drug targets. The best docking poses of target protein-BMPTSC complex structures were further subjected to molecular dynamics (MD) simulations. Molecular mechanics Poisson–Boltzmann surface area (MM-PBSA) calculations on the binding of BMPTSC with the target proteins viz. spike glycoprotein and ACE-2 protein showed energy values of −179.87 and −145.61 kJ/mol, respectively. Moreover, BMPTSC obeys Lipinski’s rule, and further in silico assessment of oral bioavailability, bioactivity scores, ADME, drug-likeness, and medicinal chemistry friendliness suggests that this molecule is a promising candidate for the COVID-19 drug discovery process.
Supplementary Information
The online version contains supplementary material available at 10.1007/s11224-022-02033-8.
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