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

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.

An efficient synthetic strategy towards arylated aminothiazoles was developed based on CH-activation as key step. The obtained compounds displayed high activity to accelerate cell-differentiation of progenitor cells towards muscle cells.Figure optionsDownload as PowerPoint slide