Modular Synthesis of Triazole-Containing Triaryl α-Helix Mimetics

被引：24

作者：

Ehlers, Ina ^{[1
]}

Maity, Prantik ^{[1
]}

Aube, Jeffrey ^{[2
,3
]}

Koenig, Burkhard ^{[1
]}

机构：

[1] Univ Regensburg, Fak Chem & Pharm, D-93040 Regensburg, Germany

[2] Univ Kansas, Dept Med Chem, Delbert M Shankel Struct Biol Ctr, Lawrence, KS 66047 USA

[3] Univ Kansas, Chem Methodol & Lib Dev Ctr, Delbert M Shankel Struct Biol Ctr, Lawrence, KS 66047 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 13期

关键词：

Helical structures; Peptidomimetics; Click chemistry; Nitrogen heterocycles; Protein-protein interactions; BIOLOGICAL EVALUATION; SOLID-PHASE; CLICK-CLICK; INHIBITORS; 1,2,3-TRIAZOLES; CYCLOADDITION; ALKYNES; MIMICS; AZIDES;

D O I：

10.1002/ejoc.201001531

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2474 / 2490

页数：17

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