Visible Light-Mediated Late-Stage Thioetherification of Mercaptopurine Derivatives.
| Autor: | Ge Y; School of Chemistry and Chemical Engineering, Southeast University, Nanjing, 211189, P. R.China., Peng Y; School of Chemistry and Chemical Engineering, Southeast University, Nanjing, 211189, P. R.China., Xie R; School of Chemistry and Chemical Engineering, Southeast University, Nanjing, 211189, P. R.China., Luo Y; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China., Li Y; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China., Chen G; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China.; Key Laboratory of Green and High-value Utilization of Salt Lake Resources, Qinghai Institute of Salt Lakes, Chinese Academy of Sciences, Xining, Qinghai, 810008, P. R. China. |
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| Jazyk: | angličtina |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Aug 27; Vol. 30 (48), pp. e202401774. Date of Electronic Publication: 2024 Aug 07. |
| DOI: | 10.1002/chem.202401774 |
| Abstrakt: | We disclose herein a novel and general radical approach to alkylthiopurines, encompassing 4 types of thiopurines, as well as their corresponding ribosides. This strategy is achieved through visible light-mediated late-stage functionalization of the sulfur atoms of mercaptopurines. The in situ-generated disulfide was proposed as the pivotal neutral intermediate for this transformation. We present herein a novel photo-mediated homolytic C-S bond formation for the preparation of alkylthiopurines and alkylthiopurine nucleosides. Despite the presence of reactive sites for the Minisci reaction, chemoselective S-alkylation remained the predominant pathway. This method allows for the late-stage introduction of a broad spectrum of alkyl groups onto the sulfur atom of unprotective mercaptopurine derivatives, encompassing 2-, 6-, and 8-mercaptopurine rings. Organoborons serve as efficient and eco-friendly alkylating reagents, providing advantages in terms of readily availability, stability, and reduced toxicity. Further derivatization of the thioetherified nucleosides, together with anti-tumor assays, led to the discovery of potent anti-tumor agents with an IC (© 2024 Wiley-VCH GmbH.) |
| Databáze: | MEDLINE |
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