A unique and rapid approach toward the efficient development of novel protein tyrosine phosphatase (PTP) inhibitors based on ‘clicked’ pseudo-glycopeptides

Yang, Jinwei; He, Xiao‐Peng; Cui, Li; Gao, Lixin; Li, Sheng; Xie, Juan; Tang, Yun; Li, Jia; Chen, Guorong

doi:10.1016/j.bmcl.2010.12.126

Cited by 33 publications

(12 citation statements)

References 40 publications

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“…586 A class of 1-O-triazole-linked threoninyl, serinyl, tyrosinyl, and phenylalaninyl sugars were developed using microwave-facilitated Cu(I)-catalyzed azide−alkyne 1,3-dipolar cycloaddition carried out by Yang and co-workers (Scheme 147). 587 These triazolyl glycopepetides were recognized as potential inhibitors of PTP1B and CDC25B with selectivity over various phosphatases. For instance, compound 594 (with IC 50 = 5.1 μM) was found to have selectivity and act as a potent inhibitor of PTP1B over other PTPs that were tested.…”

Section: Ptp1b Inhibitory Activitiesmentioning

confidence: 99%

“…For instance, compound 594 (with IC 50 = 5.1 μM) was found to have selectivity and act as a potent inhibitor of PTP1B over other PTPs that were tested. 587 A series of dimeric benzoylated and benzylated β-CD-glucosyl and β-CD-galactosyl 1,4-dimethoxy-substituted benzenes and naphthalenes were designed by the Xie group using the click approach. These compounds were subjected to ceric ammonium nitrate (CAN) oxidation, leading to the synthesis of the corresponding quinone derivatives.…”

Section: Ptp1b Inhibitory Activitiesmentioning

confidence: 99%

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Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the "click reaction", serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.

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Section: Ptp1b Inhibitory Activitiesmentioning

confidence: 99%

Section: Ptp1b Inhibitory Activitiesmentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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“…Yang et al . [64] examined a series of glycosyl triazolyl acids developed through click reactions as new protein tyrosine phosphatase inhibitors that have potential uses to treat auto-immune disorders.…”

Section: Bioconjugation To Combine Units With Different Functionsmentioning

confidence: 99%

Click Chemistry in Peptide-Based Drug Design

2013

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Click chemistry is an efficient and chemoselective synthetic method for coupling molecular fragments under mild reaction conditions. Since the advent in 2001 of methods to improve stereochemical conservation, the click chemistry approach has been broadly used to construct diverse chemotypes in both chemical and biological fields. In this review, we discuss the application of click chemistry in peptide-based drug design. We highlight how triazoles formed by click reactions have been used for mimicking peptide and disulfide bonds, building secondary structural components of peptides, linking functional groups together, and bioconjugation. The progress made in this field opens the way for synthetic approaches to convert peptides with promising functional leads into structure-minimized and more stable forms.

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“…Compounds 7 and 8 had their binding mode in the opposite direction. Docking could not give the explanation of the inhibitory activity 29,[35][36][37][38][39][40][41][42][43][44][45][46][47] , so it was necessary to synthesize these molecules and evaluated their biological activities with CDC25A and B then verification of their reversibility.…”

Section: Molecular Modellingmentioning

confidence: 99%