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硫醚向具有抗菌活性的α-硫化二硫化物的光催化双边二硫化反应

Photocatalytic Bilateral Disulfuration of Thioethers Toward α-Sulfide Disulfides With Antibacterial Activity.

作者信息

Tian Qingqiang, Wang Chuxia, Liu Bingrui, Wu Xiangwei, Li Yahui

机构信息

Anhui Provincial Key Laboratory of Hazardous Factors and Risk Control of Agri-food Quality Safety, Anhui Agricultural University, Hefei, 230036, China.

Hefei National Laboratory for Physical Sciences at the Microscale and CAS Key Laboratory of Mechanical Behavior and Design of Materials, Department of Precision Machinery and Precision Instrumentation, University of Science and Technology of China, Hefei, 230026, China.

出版信息

Adv Sci (Weinh). 2025 Jul;12(27):e2502862. doi: 10.1002/advs.202502862. Epub 2025 Apr 26.

DOI:10.1002/advs.202502862
PMID:40285683
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12279184/
Abstract

α-Sulfide disulfides represent valuable motifs in organic and pharmaceutical chemistry. However, the limited availability of synthetic approaches for α-sulfide disulfides has impeded progress in this field. In this study, a photocatalytic approach to synthesizing modifiable α-sulfide disulfides is presented using accessible sulfides and a bilateral disulfurating reagent. The reaction proceeds under mild conditions and demonstrates broad substrate compatibility, accommodating both aromatic and aliphatic sulfides. Moreover, the synthesized α-sulfide disulfides display robust reactivity in subsequent transformations with different electrophiles. Notably, this protocol can also be applied to the modification of polymer matrices. Bioassays further reveal that certain target compounds exhibit significant antibacterial activity against plant pathogens, such as Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pathovar oryzicola (Xoc), and Dickeya zeae (D. zeae).

摘要

α-硫化二硫化物是有机化学和药物化学中有价值的结构单元。然而,α-硫化二硫化物合成方法的有限可用性阻碍了该领域的进展。在本研究中,提出了一种光催化方法,使用易得的硫化物和双边双硫化试剂来合成可修饰的α-硫化二硫化物。该反应在温和条件下进行,并表现出广泛的底物兼容性,适用于芳香族和脂肪族硫化物。此外,合成的α-硫化二硫化物在随后与不同亲电试剂的转化中表现出强大的反应活性。值得注意的是,该方案还可应用于聚合物基质的改性。生物测定进一步表明,某些目标化合物对植物病原体具有显著的抗菌活性,如水稻白叶枯病菌(Xoo)、水稻条斑病菌(Xoc)和玉米细菌性枯萎病菌(D. zeae)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/992ca653f0b7/ADVS-12-2502862-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/fb0427371514/ADVS-12-2502862-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/579bd1c5b075/ADVS-12-2502862-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/f8570cb7553d/ADVS-12-2502862-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/35d212da9981/ADVS-12-2502862-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/992ca653f0b7/ADVS-12-2502862-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/fb0427371514/ADVS-12-2502862-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/579bd1c5b075/ADVS-12-2502862-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/f8570cb7553d/ADVS-12-2502862-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/35d212da9981/ADVS-12-2502862-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc41/12279184/992ca653f0b7/ADVS-12-2502862-g001.jpg

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Flavin-Mediated Photocatalysis Provides a General Platform for Sulfide C-H Functionalization.黄素介导的光催化为硫化物C-H官能团化提供了一个通用平台。
ACS Catal. 2024 Jan 31;14(4):2395-2401. doi: 10.1021/acscatal.3c05785. eCollection 2024 Feb 16.
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Construction of C-S and C-Se Bonds from Unstrained Ketone Precursors under Photoredox Catalysis.
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Angew Chem Int Ed Engl. 2024 Feb 19;63(8):e202314790. doi: 10.1002/anie.202314790. Epub 2024 Jan 18.
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Metallaphotoredox catalysis for sp C-H functionalizations through hydrogen atom transfer (HAT).通过氢原子转移(HAT)实现 sp³ C-H 官能团化的金属光氧化还原催化。
Chem Soc Rev. 2023 Jun 19;52(12):4099-4120. doi: 10.1039/d3cs00023k.
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Design of a Bilateral Disulfurating Reagent for Unsymmetrical Polysulfidation.用于不对称多硫化物的双二硫试剂的设计。
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Access to Polysulfides through Photocatalyzed Dithiosulfonylation.通过光催化二硫代磺酰化作用获得多硫化物。
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