Synthesis of 5-arylated N-arylthiazole-2-amines as potential skeletal muscle cell differentiation promoters

被引：25

作者：

Schnuerch, Michael ^{[1
]}

Waldner, Birgit ^{[1
]}

Hilber, Karlheinz ^{[2
]}

Mihovilovic, Marko D. ^{[1
]}

机构：

[1] Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria

[2] Med Univ Vienna, Inst Pharmacol, Ctr Physiol & Pharmacol, A-1090 Vienna, Austria

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 07期

关键词：

Heterocycles; CH-activation; Cell differentiation; Bioactive compound; PLURIPOTENT STEM-CELLS; CATALYZED DIRECT ARYLATION; HANTZSCH THIAZOLE SYNTHESIS; AMINO-IMINO TAUTOMERISM; HUMAN SOMATIC-CELLS; SMALL-MOLECULE; KINASE-INHIBITORS; NEURONAL DIFFERENTIATION; DEFINED FACTORS; HALOGEN DANCE;

D O I：

10.1016/j.bmcl.2011.01.123

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of N-arylthiazole-2-amines was prepared and their biological activity for the promotion of skeletal muscle cell differentiation was investigated, a process of significant importance in muscle regeneration. A versatile new synthetic route towards the target compounds was developed and the substrate scope of this methodology was investigated. Introduction of the 2-aminoaryl substituent was carried out via nucleophilic substitution reactions in excellent yields. Furthermore, the aryl in 5-position was introduced applying a direct arylation reaction, a major improvement compared to reported synthetic routes regarding atom efficiency and sustainability. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2149 / 2154

页数：6

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