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

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Nakahata, Douglas H. ; Corsino, Carlos E. S. P. ; de Morais, Guilherme C. ; Pereira, Gabriele M. ; Cruz, Allefe B. ; Pereira, Douglas Henrique ; Cassani, Natasha M. ; Ruiz, Uriel Enrique A. ; Santos, Igor A. ; Jardim, Ana Carolina G. ; Corbi, Pedro P.

• Tipo de documento: Artigo Científico
• Fonte: Journal of the Brazilian Chemical Society; v. 35, n. 11, p. 12-pg., 2024-01-01.

Resumo

This study presents the synthesis and characterization of five Schiff bases derived from the reaction of 4-(2-aminoethyl)-benzenesulfonami de (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 mu mol L-1,-1 , while compound 5 was cytotoxic at this concentration. Compound 5 was active against the Chikungunya virus at the concentration of 10 mu mol L-1,-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 mu mol L-1.-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)

• Processo FAPESP: 21/10265-8 - Centro de Inovação Teranóstica em Câncer (CancerThera)
• Beneficiário: Carmino Antonio de Souza
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs
• Processo FAPESP: 13/08293-7 - CECC - Centro de Engenharia e Ciências Computacionais
• Beneficiário: Munir Salomao Skaf
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs
• Processo FAPESP: 15/20882-3 - Complexos metálicos com sulfametoxidiazina e sulfadimetoxina: síntese, caracterização e aplicações como agentes antimicrobianos para uso tópico
• Beneficiário: Douglas Hideki Nakahata
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 17/11485-6 - Desenvolvimentos computacionais e teóricos baseados em métodos ab initio e na Teoria do Funcional de Densidade
• Beneficiário: Rogério Custodio
• Modalidade de apoio: Auxílio à Pesquisa - Regular