Adding “Energy” to Chalcogenophene Chemistry: Electrosynthesis of 2,3,5‐Trisubstituted Selenyl‐Chalcogenophenes and Their Interaction with DNA
Year: 2025
Type: article
Abstract: Herein, an efficient and more environmentally benign electrosynthetic approach is reported for the intramolecular chalcogeno cyclization of ( Z )‐chalcogenoenynes, resulting in seleno‐chalcogenophene derivatives. The reaction proceeds in an undivided cell in constant current and equipped with platinum electrodes by using 5 mL of acetonitrile as a solvent, 0.2 mmol of the ( Z )‐chalcogenoenyne, 2 equiv. of diorganoyl diselenide and 0.2 equiv. of electrolyte, 18 overall compounds are synthesized with yields between 52% and 97%. Control experiments and density functional theory studies are also conducted to propose plausible mechanistic pathways. Furthermore, selected compounds are screened via spectrophotometric titration to assess their potential interactions with DNA, with results indicating that both groove and intercalation interactions occure depending on the structure and concentration of the seleno‐chalcogenophene compound. This electrochemical procedure presents itself as a viable and cost‐effective alternative for the synthesis of chalcogenophenes, as it doesn't require external oxidants, operates under mild reaction conditions, and affords its products in good to excellent yields.
Language: English
Subfield: Toxicology
Domain: Life Sciences
Open Access status: hybrid
Estimated APC paid: $4,330
Funders: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico, Fundação de Amparo à Pesquisa do Estado de Minas Gerais, Fundação de Amparo à Pesquisa e Inovação do Estado de Santa Catarina, Instituto Nacional de Ciência e Tecnologia de Catálise em Sistemas Moleculares e Nanoestruturados
Award: G3690646728
OpenAlex ID: W4413373414