Traceless Azido Linker for the Solid-Phase Synthesis of <i>N</i>H-1,2,3-Triazoles via Cu-Catalyzed Azide−Alkyne Cycloaddition Reactions

Cohrt, A. Emil; Jensen, Jakob F.; Nielsen, Thomas E.

doi:10.1021/ol102209p

Cited by 46 publications

(30 citation statements)

References 33 publications

(19 reference statements)

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“…Alternative methods to prepare compounds 5b, 70 5i, [70][71][72] 5o, 37 and 5y 30 were reported in the literature. Since we already described the synthesis of 5a 30 and 5k 28 , these procedures are not repeated here.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

Banert¹,

Hagedorn²,

Hemeltjen³

et al. 2016

Arkivoc

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About thirty NH-1,2,3-triazoles with at least one additional functional group in a side chain at C-4 were prepared from propargyl substrates. These reactions included propargyl azides and their [3,3]-sigmatropic rearrangement to generate short-lived allenyl azides, which cyclized to form triazafulvenes that could be trapped by addition of N-or O-nucleophiles. In most cases, simple substrates and cheap sodium azide were utilized as starting compounds, and the syntheses were performed by using a one-pot procedure without isolation of any dangerous azides. This method to prepare NH-1,2,3-triazoles turned out to be compatible with quite different substitution patterns of the propargyl substrate.

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Section: Methodsmentioning

confidence: 99%

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

Banert¹,

Hagedorn²,

Hemeltjen³

et al. 2016

Arkivoc

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“…Peptide conjugate NT II was prepared following procedures B, D, and E. For the C-terminal introduction of a monosubstituted 1,2,3-triazole, a rink amide MBHA resin LL (100−200 mesh; 0.03 mmol) was used. After deprotection of the resin, its amine functionality was converted into an azide following procedure C. 47,48 The triazole was formed following general procedure D, using Fmoc-Leu-alkyne. 24 Cell Internalization Experiments.…”

Section: ■ Experimental Proceduresmentioning

confidence: 99%

1,2,3-Triazole Stabilized Neurotensin-Based Radiopeptidomimetics for Improved Tumor Targeting

et al. 2015

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Neurotensin (NT) is a regulatory peptide with nanomolar affinity toward NT receptors, which are overexpressed by different clinically relevant tumors. Its binding sequence, NT(8-13), represents a promising vector for the development of peptidic radiotracers for tumor imaging and therapy. The main drawback of the peptide is its short biological half-life due to rapid proteolysis in vivo. Herein, we present an innovative strategy for the stabilization of peptides using nonhydrolizable 1,4-disubstituted, 1,2,3-triazoles as amide bond surrogates. A "triazole scan" of the peptide sequence yielded novel NT(8-13) analogues with enhanced stability, retained receptor affinity, and improved tumor targeting properties in vivo. The synthesis of libraries of triazole-based peptidomimetics was achieved efficiently on solid support by a combination of Fmoc-peptide chemistry, diazo transfer reactions, and the Cu(I)-catalyzed alkyne azide cycloaddition (CuAAC) employing methods that are fully compatible with standard solid phase peptide synthesis (SPPS) chemistry. Thus, the amide-to-triazole substitution strategy may represent a general methodology for the metabolic stabilization of biologically active peptides.

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“…Analytical data are in accordance with those reported in the litterature. 31 Yield: 0.268 g (98%); yellow oil. 1H-1,2,3-triazole (2l) The title compound was prepared from 3h (0.232 g, 0.89 mmol) according to the general protocol for debenzylation.…”

Section: -(1h-123-riazol-4-yl)ethanol (2i)mentioning

confidence: 99%

Debenzylation of Functionalized 4- and 5-Substituted 1,2,3-Triazoles

et al. 2012

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A range of 4-and 5-substituted N-benzyl-1,2,3-triazoles have been submitted to debenzylation using Pd/C and hydrogen in the presence of 1,1,2-trichloroethane. Triazoles with oxygen-containing substituents are efficiently debenzylated under these conditions. Triazoles with a phenyl or benzyl substituent on C4 or C5 are not debenzylated, whereas a pentyl-substituted derivative was readily debenzylated.

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Traceless Azido Linker for the Solid-Phase Synthesis of NH-1,2,3-Triazoles via Cu-Catalyzed Azide−Alkyne Cycloaddition Reactions

Cited by 46 publications

References 33 publications

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

1,2,3-Triazole Stabilized Neurotensin-Based Radiopeptidomimetics for Improved Tumor Targeting

Debenzylation of Functionalized 4- and 5-Substituted 1,2,3-Triazoles

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