Resgate Da Reação De Debus-Radziszewski: Ensino Prático De Reações Multicomponentes Na Síntese Da Lofina

Santos, Victória Laysna dos Anjos; Gonsalves, Arlan de Assis; Araújo, Cleônia Roberta Melo

doi:10.21577/0100-4042.20170608

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“…Fluorescent compounds, such as naphthoxazoles, have been explored as active molecules in biological systems [ 6 ]. Imidazoles and oxazoles can be synthesized through a multicomponent reaction, the Debus–Radziszewski reaction, employing α-dicarbonyl compounds and aldehydes [ 7 , 8 ]. The same reaction generates naphthoimidazoles and naphthoxazoles in which 1,2-naphthoquinones are used as α-dicarbonyl compounds [ 9 , 10 ].…”

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confidence: 99%

Naphth[1,2-d]imidazoles Bioactive from β-Lapachone: Fluorescent Probes and Cytotoxic Agents to Cancer Cells

et al. 2023

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Theranostics combines therapeutic and imaging diagnostic techniques that are extremely dependent on the action of imaging agent, transporter of therapeutic molecules, and specific target ligand, in which fluorescent probes can act as diagnostic agents. In particular, naphthoimidazoles are potential bioactive heterocycle compounds to be used in several biomedical applications. With this aim, a group of seven naphth[1,2-d]imidazole compounds were synthesized from β-lapachone. Their optical properties and their cytotoxic activity against cancer cells and their compounds were evaluated and confirmed promising values for molar absorptivity coefficients (on the order of 103 to 104), intense fluorescence emissions in the blue region, and large Stokes shifts (20–103 nm). Furthermore, the probes were also selective for analyzed cancer cells (leukemic cells (HL-60). The naphth[1,2-d]imidazoles showed IC50 between 8.71 and 29.92 μM against HL-60 cells. For HCT-116 cells, values for IC50 between 21.12 and 62.11 μM were observed. The selective cytotoxicity towards cancer cells and the fluorescence of the synthesized naphth[1,2-d]imidazoles are promising responses that make possible the application of these components in antitumor theranostic systems.

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