Synthesis of Triazole‐Linked Amino Acid‐Aryl C‐Glycoside Hybrids via Click Chemistry as Novel PTP1B Inhibitors |
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| Authors: | Jia Wang Xiaopeng He Lixin Gao Li Sheng Xiaoxin Shi Jia Li Guorong Chen |
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| Institution: | 1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, and School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China;2. National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, China |
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| Abstract: | Triazolyl phenylalanine and tyrosine‐aryl C‐glycoside hybrids were readily synthesized via microwave‐assisted Cu(I)‐catalyzed azide‐alkyne 1,3‐dipolar cycloaddition in high yields. Successive enzymatic assay identified the synthesized glycoconjugates as novel PTP1B inhibitors with low micromole‐ranged inhibitory activity and at least several‐fold selectivity over other homologous PTPs tested. In addition, the benzyl groups on glucosyl moiety were found crucial toward PTP1B inhibition. |
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| Keywords: | click chemistry C‐glycoside triazolyl amino acid PTP inhibitors |
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