Synthesis of imidazo[1,2- a]pyridine-containing peptidomimetics by tandem of Groebke-Blackburn-Bienaymé and Ugi reactions

Abstract

Peptidomimetics with a substituted imidazo[1,2-a]pyridine fragment were synthesized by a tandem of Groebke-Blackburn-Bienaymé and Ugi reactions. The target products contain substituted imidazo[1,2-a]pyridine and peptidomimetic moieties as pharmacophores with four diversity points introduced from readily available starting materials, including scaffold diversity. A small focused compound library of 20 Ugi products was prepared and screened for antibacterial activity.

Keywords: Groebke–Blackburn–Bienaymé reaction; Ugi reaction; imidazo[1,2-a]pyridine; isocyanide; multicomponent reaction; peptidomimetic.