DDQ/Fe(NO3)3-Catalyzed Aerobic Synthesis of 3-Acyl Indoles and an In Silico Study for the Binding Affinity of N-Tosyl-3-acyl Indoles toward RdRp against SARS-CoV-2

• DOI: 10.1021/acs.joc.2c02009
• Publication Date: 2023-01-09T16:47:20Z
• Authors: Gopal Rana; Abhishek Kar; Sandip Kundal; Dulal Musib; Umasish Jana
• Keywords: Tosyl

In the present study, we herein report a DDQ-catalyzed new protocol for synthesis of substituted 3-acylindoles. Being potential system virtual hydrogen storage, introduction catalytic DDQ in combination with Fe(NO3)3·9H2O and molecular oxygen as co-catalysts offers regioselective oxo-functionalization C-3 alkyl-/aryllidine indolines even scale-up investigations. Intermediate isolation, their spectroscopic characterization, density functional theory calculations indicate that method involves dehydrogenative allylic hydroxylation 1,3-functional group isomerization/aromatization followed by terminal oxidation to afford 3-acylindoles quantitatively very high regioselectivity. This is general large number substrates varieties groups tolerance emerging high-yield outcome. Moreover, docking studies were performed some selected ligands an RNA-dependent RNA polymerase complex (RdRp complex) SARS-CoV-2 illustrate binding those ligands. The results revealed few possess inhibit RdRp SARS-Cov-2 energies (−6.7 −8.19 kcal/mol), which are comparably higher respect reported conventional re-purposed drugs such Remdesivir, Ribavirin, so forth (−4 −7 kcal/mol).