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
收藏
页码：6145 / 6154
页数：10
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