A simbiótica relação entre para-quinonas substituídas no anel A e 𝜷-lapachonas para identificação de compostos bioativos: síntese e potencial atividade contra o vírus SARS-CoV-2

Abstract

In the present work, strategies for obtaining new quinone derivatives through the synthesis of 1,2,3-triazole rings through Huisgen 1,3-dipolar cycloaddition reactions catalyzed by copper(I) were described. Ten new naphthoquinoidal derivatives were synthesized. These compounds have two quinoid centers joined through the triazole ring and the compounds obtained therefore have two redox nuclei, which is interesting from a biological point of view. Product variability was achieved by combining two β-lapachone derivatives containing the azido group with five naphthoquinoid substrates containing substituted groups in the A ring. The regioselectivity resulting from the alkyne formation reaction was studied by nuclear magnetic resonance spectroscopy. two-dimensional with a detailed analysis of the respective spectra. The unequivocal confirmation of the structure was also performed by X-ray diffraction studies. The interaction of these new compounds with two enzymes known as Mpro and PLpro, responsible for the replication of the SARS-CoV-2 COVID-19 virus were analyzed through molecular modeling calculations. Biological studies for the compounds obtained are in the final phase of completion in our laboratories.