| Summary: | Dapsone (DDS) is an antibacterial drug with well-known antioxidant properties. However, the antioxidant behavior of its derivatives has not been well explored. In the present work, the antioxidant activity of 10 dapsone derivatives 4-substituted was determined by an evaluation in two in vitro models (DPPH radical scavenging assay and ferric reducing antioxidant power). These imine derivatives <b>1</b>–<b>10</b> were obtained through condensation between DDS and the corresponding aromatic aldehydes 4-substuited. Three derivatives presented better results than DDS in the determination of DPPH (<b>2</b>, <b>9</b>, and <b>10</b>). Likewise, we have three compounds with better reducing activity than dapsone (<b>4</b>, <b>9</b>, and <b>10</b>). In order to be more insight, the redox process, a conceptual DFT analysis was carried out. Molecular descriptors such as electronic distribution, the total charge accepting/donating capacity (I/A), and the partial charge accepting/donating capacity (ω<sup>+</sup>/ω<sup>−</sup>) were calculated to analyze the relative donor-acceptor capacity through employing a donor acceptor map (DAM). The DFT calculation allowed us to establish a relationship between GAP<sub>HOMO-LUMO</sub> and DAM with the observed antioxidant effects. According to the results, we concluded that compounds <b>2</b> and <b>3</b> have the lowest <i>R<sub>a</sub></i> values, representing a good antioxidant behavior observed experimentally in DPPH radical capturing. On the other hand, derivatives <b>4</b>, <b>9</b>, and <b>10</b> display the best reducing capacity activity with the highest ω<sup>−</sup> and <i>R<sub>d</sub></i> values. Consequently, we propose these compounds as the best antireductants in our DDS imine derivative series.
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