Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide and Sulfonate Ester Derivatives

• Published in: Journal of the Brazilian Chemical Society 2022-06, Vol.33 (6), p.556-569
• Main Authors: Pacheco, Paulo, Gonzaga, Daniel, Cirne-Santos, Cláudio, Barros, Caroline, Gomes, Max, Gomes, Rafaela, Gonçalves, Mariana, Ferreira, Vitor, Rabelo, Vitor, Abreu, Paula, Faria, Robson, de Resende, Gabriel, da Rocha, David, Paixão, Izabel, da Silva, Fernando
• Format: Article
• Language: English
• Subjects: CHEMISTRY, MULTIDISCIPLINARY
• ISSN: 0103-5053; 1678-4790
• DOI: 10.21577/0103-5053.20220010

Chikungunya virus (CHIKV) is a re-emerging disease caused by an alphavirus of the Togaviridae family. Since its first description in 1952, the disease has spread worldwide, affecting populations in both tropical and temperate countries. To date, there is no licensed vaccine or specific pharmacological treatment. Therefore, there is an increasing urgency in developing new antiviral drugs capable of specifically inhibiting viral replication. In the present work, we report the synthesis and antiviral activity evaluation of nineteen naphthoquinone derivatives, containing a sulfonamide or sulfonate group. Cell viability assays indicated a low toxic potential for all tested compounds and inhibitory assays against CHIKV identified five compounds with potent activity. The compounds were also evaluated for their virucidal potential, and the results demonstrated that compound 11a exhibited a virucidal effect higher than 70% in the treatment with 20 µM. Furthermore, in silico studies were performed to predict the antiviral drug targets.