Synthesis, Characterization and in vitro Evaluation of 4-(2-Aminoethyl)benzenesulfonamide Schiff Bases against Arboviruses

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Douglas H. Nakahata ; Carlos E. S. P. Corsino ; Guilherme C. de Morais ; Gabriele M. Pereira ^[4] ; Állefe B. Cruz ^[5] ; Douglas Henrique Pereira ; Natasha M. Cassani ^[7] ; Uriel Enrique A. Ruiz ^[8] ; Igor A. Santos ^[9] ; Ana Carolina G. Jardim ; Pedro P. Corbi ^[11]

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 35, n. 11 2024-05-10.

Abstract

This study presents the synthesis and characterization of five Schiff bases derived from the reaction of 4-(2-aminoethyl)-benzenesulfonamide (compound 1) with corresponding aldehydes, (benzaldehyde, 2-pyridinecarboxaldehyde, 2-quinolinecarboxaldehyde, 8-hydroxy2-quinolinecarboxaldehyde and 4-imidazolecarboxaldehyde, for compounds 2-6, respectively). Characterization was performed by various spectroscopic techniques and supported by density functional theory (DFT) calculations. The crystal structures revealed how the substituent groups influenced the present supramolecular interactions. Compounds 1-4 and 6 showed no cytotoxicity to BHK-21 and VERO E6 cells at the highest concentration of 50 µmol L-1, while compound 5 was cytotoxic at this concentration. Compound 5 was active against the Chikungunya virus at the concentration of 10 µmol L-1, highlighting the effect of the 8-hydroxyquinoline substituent for the antiviral activity. For Zika virus, compound 6 was the only one active at 50 µmol L-1. The results suggest the potential of combining sulfonamides with other chemotypes for further development of antiviral agents, especially in the treatment of arboviral diseases. (AU)

• FAPESP's process: 15/20882-3 - Metal complexes of sulfamethoxydiazine and sulfadimethoxine: synthesis, characterization and applications as antimicrobial agents for topical use
• Grantee: Douglas Hideki Nakahata
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 13/08293-7 - CCES - Center for Computational Engineering and Sciences
• Grantee: Munir Salomao Skaf
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 17/11485-6 - Computational and theoretical developments based on ab initio methods and the Density Functional Theory
• Grantee: Rogério Custodio
• Support Opportunities: Regular Research Grants
• FAPESP's process: 21/10265-8 - Cancer Theranostics Innovation Center (CancerThera)
• Grantee: Carmino Antonio de Souza
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC