Design and synthesis of thienylpyridyl garlands as non-peptidic alpha helix mimetics and potential protein-protein interactions disruptors

被引：24

作者：

De Giorgi, Marcella ^{[1
,2
]}

Voisin-Chiret, Anne Sophie ^{[1
]}

Santos, Jana Sopkova-de Oliveira ^{[1
]}

Corbo, Filomena ^{[1
]}

Franchini, Carlo ^{[2
]}

Rault, Sylvain ^{[1
]}

机构：

[1] Univ Caen Basse Normandie, UFR Sci Pharmaceut, Ctr Etudes & Rech Medicament Normandie, UPRES EA 4258,FR CNRS INC3M 3038, F-14032 Caen, France

[2] Univ Bari, Dept Pharmaceut Chem, I-70125 Bari, Italy

来源：

TETRAHEDRON | 2011年 / 67卷 / 34期

关键词：

Boron; Cross-coupling; Palladium; Pyridine; Thiophene; HALOPYRIDINYLBORONIC ACIDS; ESTERS;

D O I：

10.1016/j.tet.2011.06.074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes an efficient route leading to new thienylpyridyl garlands as non-peptidic alpha helix mimetics and potential protein protein interactions disruptors. Firstly, we have studied the reactivity of boronic acids and halogenated pyridines and/or thiophenes towards the Suzuki-Miyaura cross-coupling reaction in order to obtain bis-thienylpyridines. Secondly, we have functionalized these compounds by a reaction of bromination and the resultant bis-bromothienylpyridines have been found to undergo iterative Pd-catalyzed coupling based on a pseudo-Garlanding approach with a range of pyridyl boronic acids to produce a new library of thienylpyridyl oligomers. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6145 / 6154

页数：10

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