Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(48)

Published: June 26, 2024

We disclose herein a novel and general radical approach to alkylthiopurines, encompassing 4 types of thiopurines, as well their corresponding ribosides. This strategy is achieved through visible light-mediated late-stage functionalization the sulfur atoms mercaptopurines. The in situ-generated disulfide was proposed pivotal neutral intermediate for this transformation. present photo-mediated homolytic C-S bond formation preparation alkylthiopurines alkylthiopurine nucleosides. Despite presence reactive sites Minisci reaction, chemoselective S-alkylation remained predominant pathway. method allows introduction broad spectrum alkyl groups onto atom unprotective mercaptopurine derivatives, 2-, 6-, 8-mercaptopurine rings. Organoborons serve efficient eco-friendly alkylating reagents, providing advantages terms readily availability, stability, reduced toxicity. Further derivatization thioetherified nucleosides, together with anti-tumor assays, led discovery potent agents an IC

Language: Английский