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Schiff bases are diverse organic compounds with an azomethine structure (–C=N–), holding potential in both chemistry and biology. They serve as catalysts, stabilizers, and exhibit various biological activities. The molecular structure of Schiff bases influences their biological properties, including antimicrobial effects. Redox-active compounds with more negative potentials tend to be more effective against microbes. In one of our recent studies, we explored the antimicrobial properties of two Schiff bases derivatives, SB-1 ((E)-4-amino-3-((3,5-di-tert-butyl-2-hydroxybenzylidene)amino) and SB-2 ((E)-2-((4-nitrobenzilidene)amino)aniline). SB-1 showed antibacterial activity against certain Gram-positive bacteria, while SB-2 did not. The difference in their cyclic voltametric profiles, especially SB-1’s more negative reduction potential, prompted us to carry out further characterizations, including scan-rate studies, solvent analysis, and computational calculations. We found that SB-1, which presents a stable intramolecular hydrogen bond, undergoes irreversible oxidation, likely at the –NH2 group, and a quasi-reversible reduction via an intramolecular reductive coupling of the (–C=N–) azomethine group, supported by orbital theoretical calculations. This research sheds light on the potential applications of Schiff bases in antimicrobial contexts, guided by their redox properties and structure. –C=N–, CN –C=N– , C N biology catalysts stabilizers activities effects Redoxactive Redox active microbes studies derivatives SB1 SB 1 SB- E4amino33,5ditertbutyl2hydroxybenzylideneamino E4amino335ditertbutyl2hydroxybenzylideneamino Eaminoditertbutylhydroxybenzylideneamino E 4 amino 3 3,5 di tert butyl 2 hydroxybenzylidene 5 ((E)-4-amino-3-((3,5-di-tert-butyl-2-hydroxybenzylidene)amino SB2 E24nitrobenzilideneaminoaniline. E24nitrobenzilideneaminoaniline Enitrobenzilideneaminoaniline nitrobenzilidene aniline . ((E)-2-((4-nitrobenzilidene)amino)aniline) Grampositive Gram positive bacteria not profiles SB1s SBs s characterizations scanrate scan rate analysis calculations SB1, 1, bond oxidation NH2 NH –NH group quasireversible quasi reversible (–C=N– contexts –C=N E4amino33 5ditertbutyl2hydroxybenzylideneamino ditertbutyl hydroxybenzylideneamino 35 3, nitrobenzilideneaminoaniline ((E)-2-((4-nitrobenzilidene)amino)aniline (–C=N Eamino E4amino3 ditertbutylhydroxybenzylideneamino E4amino