Modular Assembly of Heterotrifunctional Molecules Enabled by Iodosulfonylation of Allenes and Subsequent Amination

Beyond the rapid achievements of therapeutic heterobifunctional molecules, some recent efforts have focused on constructing heterotrifunctional molecules, aiming at developing more potent and selective therapeutic agents or emerging additional functions to heterobifunctional molecules. However, the synthesis of these complex molecules requires a specific design and lengthy steps. We have developed a two-step strategy for the modular construction of heterotrifunctional molecules, enabled by the sustainable and convenient iodosulfonylation of allenes followed by S<sub>N</sub>2'-selective amination. This strategy successfully incorporates a broad range of biologically active molecules, labeling them with a fluorescent group. The applications of the obtained compounds in selective protein labeling, subcellular imaging, and targeted inhibition of tumor cells make this strategy highly appealing.

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Publication Details

Journal
Journal of Medicinal Chemistry
Published
2024-11-20
DOI
https://doi.org/10.1021/acs.jmedchem.4c02114
Citations
5
Primary Topic
Click Chemistry and Applications
Type
article
Field-Weighted Citation Impact
1.25

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article

Modular Assembly of Heterotrifunctional Molecules Enabled by Iodosulfonylation of Allenes and Subsequent Amination

Xiang Jiao, Qichen Zhan, Tao Cao, Binyan Lin et al.
5 citations
Journal of Medicinal Chemistry
Click Chemistry and Applications
1.25
article

Modular Assembly of Heterotrifunctional Molecules Enabled by Iodosulfonylation of Allenes and Subsequent Amination

Xiang Jiao, Qichen Zhan, Tao Cao, Binyan Lin, Peng Cao, Shijie Liu, Xiaofeng Lin
article en
5 citations

Abstract

Beyond the rapid achievements of therapeutic heterobifunctional molecules, some recent efforts have focused on constructing heterotrifunctional molecules, aiming at developing more potent and selective therapeutic agents or emerging additional functions to heterobifunctional molecules. However, the synthesis of these complex molecules requires a specific design and lengthy steps. We have developed a two-step strategy for the modular construction of heterotrifunctional molecules, enabled by the sustainable and convenient iodosulfonylation of allenes followed by S<sub>N</sub>2'-selective amination. This strategy successfully incorporates a broad range of biologically active molecules, labeling them with a fluorescent group. The applications of the obtained compounds in selective protein labeling, subcellular imaging, and targeted inhibition of tumor cells make this strategy highly appealing.

Journal of Medicinal ChemistryVol. 67(23)
Nanjing University of Chinese Medicine (CN), Wenzhou Medical University (CN), Quzhou City People's Hospital (CN)
National Natural Science Foundation of China, Nanjing University of Chinese Medicine, National Key Research and Development Program of China
Clean water and sanitation
Openalex Percentile: Top 22%
Click Chemistry and Applications
1.25
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Modular Assembly of Heterotrifunctional Molecules Enabled by Iodosulfonylation of Allenes and Subsequent Amination — Xiang Jiao, Qichen Zhan, et al. · Journal of Medicinal Chemistry (2024) | TGRS Research Map | TGRS