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

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.