Chikungunya fever is an arboviral disease that manifests as an acute illness, whose symptoms include fever, rash, and severe, debilitating arthralgia. Despite its low mortality rate, the disease can present severe forms, especially in at-risk groups such as neonates, the elderly, and individuals with comorbidities. In the search for new drugs to treat the disease, our group has been exploring N-acylhydrazone as a privileged structure in medicinal chemistry. Quinolines and their chemical derivatives have been assayed against a diverse panel of viruses with promising results. In this project, we hybridised the N-acylhydrazone with the 7-Chloroquinoline ring to produce a series of 33 compounds, which were synthesised, purified and subjected to antiviral activity assays to determine their Half Maximal Effective Concentration (EC₅₀) against the virus and the Cytotoxic Concentrations 50% (CC₅₀) against the host cells (Dose-response curves with 10 dilution points). Three compound exhibited EC₅₀ values lower than 10 µM: GPQF-8Q33 (EC_50: 0.56 µM; SI: 77.7), GPQF-8Q28 (EC₅₀: 1.26 µM; SI: 79.4) and GPQF-8Q34 (EC₅₀: 9.08 µM; SI: 40). These compounds were in silico docked into the NsP2 protease, a potential target of the virus and exhibited a panel of interaction consistent with molecular recognition. Molecular dynamics simulation corroborates the stability of the complexes as well as indicates which interactions are mostly predominant in recognition binding. Synthesis was accomplished by simple coupling of aldehydes with quinoline-hydrazines, in mild conditions (EtOH/AcOH, 80ºC, 24h). Docking studies were performed after a cross-docking assay, using Autodock software and considering a GRID centred at Trp1084 and with dimensions of 54x54x54 points. Molecular dynamics simulation of 400 ns was performed at 300ºC, considering steps of 1 fs each. Chamm-gui web-based software and Gromacs were employed in these studies.