Angewandte Chemie International Edition · 2023 · 13 citations · 14 references
PharmacyChemistryMedicinal ChemistryCombinatorial ChemistryDrug DiscoverySynthetic Medicinal ChemistryChemical Space ExplorationDiversity-oriented SynthesisMacrocycle SynthesisPeptide ChemistryChemical Space DesignMechanistic ElucidationPeptide Bond TautomerismPyrazole ChemistryPyrazole Synthesis
Multicomponent reactions are of utmost importance at generating a unique, wide, and complex chemical space. Herein we describe a novel multicomponent approach based on the combination of the isonitrile-tetrazine (4+1) cycloaddition and the Ugi four-component reaction to generate pyrazole amide derivatives. The scope of the reaction as well as mechanistic insights governing the 4H-pyrazol-4-imine tautomerization are provided. This multicomponent process provides access to a new chemical space of pyrazole amide derivatives and offers a tool for peptide modification and stapling.
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Strategies for Innovation in Multicomponent Reaction Design
Bruce Ganem · Accounts of Chemical Research · 2009 · 1.2K citations · Full text
Stapled Peptides with Improved Potency and Specificity That Activate p53
Christopher J. Brown, Soo Tng Quah, J.G.Y. de Jong et al. · ACS Chemical Biology · 2012 · 215 citations