ChemicalBook--->CAS DataBase List--->1825355-56-3

1825355-56-3

1825355-56-3 Structure

1825355-56-3 Structure
IdentificationBack Directory
[Name]

Ribocil-C
[CAS]

1825355-56-3
[Synonyms]

Ribocil-C
4(3H)-Pyrimidinone, 2-[(3S)-1-[[1-(2-pyrimidinyl)-1H-imidazol-4-yl]methyl]-3-piperidinyl]-6-(2-thienyl)-
[Molecular Formula]

C21H21N7OS
[MOL File]

1825355-56-3.mol
[Molecular Weight]

419.5
Chemical PropertiesBack Directory
[Boiling point ]

672.0±65.0 °C(Predicted)
[density ]

1.47±0.1 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

DMSO : ≥ 24.6 mg/mL (58.64 mM)
[form ]

Solid
[pka]

8.44±0.50(Predicted)
[color ]

White to off-white
[SMILES]

O=C1NC([C@@]2([H])CCCN(CC3=CN(C4=NC=CC=N4)C=N3)C2)=NC(C5=CC=CS5)=C1
Safety DataBack Directory
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

Ribocil-C is a highly selective inhibitor of bacterial riboflavin riboswitches.
[Biological Activity]

Ribocil-C is a potent inhibitor of bacterial riboflavin riboswitches. Riboswitches are cis regulatory elements present in non-coding RNA th at specifically bind to natural ligands to regulate gene expression. Ribocil-C blocks the flavin mononucleotide riboswitch-mediated expression of the ribB genewhich is required for riboflavin biosynthesiswith an IC50 value of 23 nM. Ribocil-C inhibited bacterial cell growth of E. coli MB5746 and bacterial burden in a mouse E. coli septicaemia model of infection.
[in vivo]

Higher dose Ribocil-C treatment groups (60 and 120 mg kg21 ribocil-C) demonstrate a dose-dependent reduction in bacterial burden of 1.87 and 3.29 log10[CFU per g spleen] reduction respectively versus shamtreated mice, without mortality or gross effects of toxicity observed[2].

[References]

[1] Wang H, et al. Dual-Targeting Small-Molecule Inhibitors of the Staphylococcus aureus FMN Riboswitch DisruptRiboflavin Homeostasis in an Infectious Setting. Cell Chem Biol. 2017 May 18;24(5):576-588. DOI:10.1016/j.chembiol.2017.03.014
[2] Howe JA, et al. Selective small-molecule inhibition of an RNA structural element. Nature. 2015 Oct 29;526(7575):672-7. DOI:10.1038/nature15542
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