A regioselective construction of N2-acyl-C4-aryl-aminoimidazoles is presented. Previous syntheses of related 2-acylaminoimidazoles relied on a metal or base catalyzed hydroamination of propargylguanidines, yet inherently could not deliver C4 aryl substitution. A subset of 16 compounds derived from three amino acids were constructed in order to yield insight into the reaction’s scope. The biological evaluation of these N2-acyl-C4-aryl-aminoimidazoles in the context of breast cancer has allowed for the elucidation of a scaffold that induces zinc dyshomeostasis specifically in multiple transformed cell lines in vitro.

Regioselective construction of N2-acyl-C4-aryl-aminoimidazoles

253rd National Meeting (2017)

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