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基于2-异氰基芳基硒醚/硫醚和糖基溴化物的光氧化还原催化合成α-苯并硒唑基/苯并噻唑基糖苷

Photoredox-Catalyzed Synthesis of -Benzoselenazolyl/Benzothiazolyl Glycosides from 2-Isocyanoaryl Selenoethers/Thioethers and Glycosyl Bromides.

作者信息

Jiao Yi, Shi Xiaoran, Ju Lei, Yu Shouyun

机构信息

State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.

Sunichem Company, Limited, Dandong 118003, China.

出版信息

Org Lett. 2024 Jan 12;26(1):390-395. doi: 10.1021/acs.orglett.3c04059. Epub 2024 Jan 2.

Abstract

Molecules containing heteroatoms, such as Se and S, play an indispensable role in the discovery and design of pharmaceuticals, whereas Se has been less studied. Here, we described a photoredox strategy to synthesize -benzoselenazolyl (Bs) glycosides from 2-isocyanoaryl selenoethers and glycosyl bromides. This reaction was carried out under mild conditions with high efficiency. -Benzothiazolyl (Bt) glycosides could also be synthesized from 2-isocyanoaryl thioethers using this strategy. This method can access novel seleno/thiosugars, which will benefit Se/S-containing drug discovery.

摘要

含有杂原子(如硒和硫)的分子在药物的发现和设计中起着不可或缺的作用,而对硒的研究较少。在此,我们描述了一种光氧化还原策略,用于从2-异氰基芳基硒醚和糖基溴合成β-苯并硒唑基(Bs)糖苷。该反应在温和条件下高效进行。使用该策略也可以从2-异氰基芳基硫醚合成β-苯并噻唑基(Bt)糖苷。该方法可以获得新型的硒/硫代糖,这将有助于含硒/硫药物的发现。

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