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Robenidine ( E )‐ N ′‐(( E )‐1‐(4‐chlorophenyl)ethylidene)‐2‐(1‐(4‐chlorophenyl)ethylidene)hydrazine‐1‐carboximidhydrazide displays methicillin‐resistant  Staphyoccoccus aureus  (MRSA) and vancomycin‐resistant Enterococci (VRE) MICs of 2 μg mL −1 . Herein we describe the structure‐activity relationship development of a novel series of guanidine to 2‐aminopyrimidine isosteres that ameliorate the low levels of mammalian cytotoxicity in the lead compound while retaining good antibiotic activity. Removal of the 2‐NH 2  pyrimidine moiety renders these analogues inactive. Introduction of a central 2‐NH 2  triazine moiety saw a 10‐fold activity reduction. Phenyl to cyclohexyl isosteres were inactive. The 4‐BrPh and 4‐CH 3 Ph with MIC values of 2 and 4 μg mL −1 , against MRSA and VRE respectively, are promising candidates for future development.

Discovery of 4,6‐bis(2‐(( E )‐benzylidene)hydrazinyl)pyrimidin‐2‐Amine with Antibiotic Activity