1. Synthetic enzyme-catalyzed multicomponent reaction for Isoxazol-5(4 H )-one Syntheses, their properties and biological application; why should one study mechanisms?
- Author
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Oliveira GHC, Ramos LM, de Paiva RKC, Passos STA, Simões MM, Machado F, Correa JR, and Neto BAD
- Subjects
- Anti-Bacterial Agents chemical synthesis, Anti-Bacterial Agents chemistry, Catalysis, Isoxazoles chemical synthesis, Isoxazoles chemistry, Microbial Sensitivity Tests, Molecular Structure, Anti-Bacterial Agents pharmacology, Gram-Negative Bacteria drug effects, Gram-Positive Bacteria drug effects, Isoxazoles pharmacology, Peptides chemistry
- Abstract
In this work, we describe the application of a synthetic enzyme (synzyme) as the catalyst to promote the multicomponent synthesis of isoxazol-5(4H)-one derivatives. The catalytic system could be used up to 15 times without any notable loss of its activity. Some derivatives showed fluorescence and their photophysical data were evaluated. The mechanism of the reaction was, for the first time, investigated and, among the three reaction pathway possibilities, only one was operating under the developed conditions. ESI-MS(/MS) allowed for both the simultaneous monitoring of the multicomponent reaction (MCR) and the proposition of a kinetic model to explain the transformation. The kinetic model pointed firmly to only one reaction pathway and helped to discard the other two possibilities. The antimicrobial abilities of all synthesized derivatives against Gram-positive and Gram-negative strains were also evaluated. The abilities of functional chromophores (fluorescent compounds) as live cell-imaging probes were verified and one of the multicomponent adducts could stain early endosomes selectively in bioimaging experiments.
- Published
- 2021
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