Compound ID | 2844

Update compound information

NCL195

Synonym(s): 2-aminopyrimidine robenidine analogue  |  4,6-bis-[2-((E)−4-methylbenzylidene)hydrazinyl]pyrimidin-2-amine

Class: Small molecule antibacterial agent

Agent Type: Synthetic; Small molecule;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Unknown
Target Pathogen: Active against Staphylococcus aureus, Streptococcus pneumoniae, vancomycin-resistant Enterococcus, and when in combination with colistin/polymyxin B to Escherichia coli, Acinetobacter baumannii, Klebsiella pneumoniae, and Pseudomonas aeruginosa
Description: Synthetic compound based on the anticoccidial agent robenidine; shows synergistic effect with sub-inhibitory concentrations of colistin when used in MDR Gram-negative infection model; superior efficacy when administered via oral route than systemic route
Institute where first reported: The University of Adelaide, Adelaide, South Australia, Australia
Year first mentioned: 2017
Development status: Experimental
Chemical structure(s):
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Molecular weight: 359.43
Iso. SMILES: CC1=CC=C(C=C1)/C=N\NC2=CC(=NC(=N2)N)N/N=C\C3=CC=C(C=C3)C
InChI Key: CPKDCTZSBHOGOC-YFBGDSSHSA-N
Can. SMILES: CC1=CC=C(C=C1)/C=N\NC2=NC(=NC(=C2)N/N=C\C3=CC=C(C)C=C3)N
InChI: InChI=1S/C20H21N7/c1-14-3-7-16(8-4-14)12-22-26-18-11-19(25-20(21)24-18)27-23-13-17-9-5-15(2)6-10-17/h3-13H,1-2H3,(H4,21,24,25,26,27)/b22-12-,23-13-
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/131746624
Citations:
  • https://pubs.acs.org/doi/10.1021/acs.jmedchem.5b01797
  • https://www.science.org/doi/10.1126/science.168.3929.373
  • https://journals.asm.org/doi/10.1128/aac.00424-23

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