Modular Synthesis of Triazole-Containing Triaryl alpha-Helix Mimetics

Ehlers, Ina and Maity, Prantik and Aube, Jeffrey and Koenig, Burkhard (2011) Modular Synthesis of Triazole-Containing Triaryl alpha-Helix Mimetics. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (13). pp. 2474-2490. ISSN 1434-193X,

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Abstract

We describe novel scaffold designs for nonpeptidic alpha-helix mimetics. The tricyclic scaffolds contain triazoles and reproduce amino acid side chains i, i+3, and i+7. The three different scaffolds are synthetically readily accessible, allow the introduction of further substituents to increase the versatility, and are suitable for library design. A modular synthesis route using Cu-I- and Ru-II-catalyzed azide-alkyne [3+2] cycloadditions as central steps was developed. To demonstrate the methodology, we have prepared a library of compounds containing all three scaffolds.

Item Type: Article
Uncontrolled Keywords: PROTEIN-PROTEIN INTERFACES; BIOLOGICAL EVALUATION; TERMINAL ALKYNES; SOLID-PHASE; CLICK-CLICK; INHIBITORS; AZIDES; MIMICS; FUNCTIONALIZATION; 1,2,3-TRIAZOLES; Helical structures; Peptidomimetics; Click chemistry; Nitrogen heterocycles; Protein-protein interactions
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 22 Jun 2020 06:34
Last Modified: 22 Jun 2020 06:34
URI: https://pred.uni-regensburg.de/id/eprint/20894

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