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

ABSTRACT: 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??g?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-NH2 pyrimidine moiety renders these analogues inactive. Introduction of a central 2-NH2 triazine moiety saw a 10-fold activity reduction. Phenyl to cyclohexyl isosteres were inactive. The 4-BrPh and 4-CH3Ph with MIC values of 2 and 4??g?mL-1, against MRSA and VRE respectively, are promising candidates for future development.

SUBMITTER: Russell CC 

PROVIDER: S-EPMC6610448 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Discovery of 4,6-bis(2-((<i>E</i>)-benzylidene)hydrazinyl)pyrimidin-2-Amine with Antibiotic Activity.

Russell Cecilia C CC   Stevens Andrew A   Young Kelly A KA   Baker Jennifer R JR   McCluskey Siobhann N SN   Khazandi Manouchehr M   Pi Hongfei H   Ogunniyi Abiodun A   Page Stephen W SW   Trott Darren J DJ   McCluskey Adam A  

ChemistryOpen 20190704 7

Robenidine (<i>E</i>)-<i>N</i>'-((<i>E</i>)-1-(4-chlorophenyl)ethylidene)-2-(1-(4-chlorophenyl)ethylidene)hydrazine-1-carboximidhydrazide displays methicillin-resistant <i>Staphyoccoccus aureus</i> (MRSA) and vancomycin-resistant Enterococci (VRE) MICs of 2 μg mL<sup>-1</sup>. 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  ...[more]

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