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[ CAS No. 563-96-2 ] {[proInfo.proName]}

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Chemical Structure| 563-96-2
Chemical Structure| 563-96-2
Structure of 563-96-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 563-96-2 ]

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Product Citations

Product Citations

Suresh, Dittu ; Yu, Tsz Tin ; Kuppusamy, Rajesh , et al. DOI:

Abstract: Antimicrobial resistance has grown to become a global crisis consistently participating in the death of millions worldwide and accumulating costs on healthcare. Quorum sensing inhibition is a new alternative antimicrobial strategy that has been gaining attention due to its ability to suppress the resistance of Pseudomonas aeruginosa (PA). This approach shows great potential in overcoming bacterial resistance and could provide a much needed substitute to conventional antibiotics in the future. PA has 3 main quorum sensing systems of which the Las system has been identified to be the most viable therapeutic target. In this study, we report the synthesis of a library of novel broad-spectrum quorum sensing inhibitors from the dihydroyrrol-2-one scaffold to form urea and imidazolium analogues. Molecular docking was performed in parallel to synthesis to aid design. It also confirmed that the molecules comfortably occupy the ligand binding domain in addition to potential key interactions commonly present in LasR inhibitors. As predicted, these compounds displayed low bactericidal effects against P. aeruginosa with most compounds exhibiting MIC of > 250 μM, while maintaining moderate activity towards Escherichia coli with the most potent compound having an MIC of 32 μM. The greatest bactericidal effects were present on Staphylococcus aureus with the thiourea based molecule 10c showed the highest antibacterial activity with MIC of 16 μM. Furthermore, several molecules displayed highly potent quorum sensing inhibitory activity with compounds 10g and 9e both demonstrating over 70% inhibition respectively of the LasR system at 16 μM. These compounds also expressed inhibition of pyocyanin within P. aeruginosa and haemolytic assay indicates a low level of cell lysis and hence low toxicity of the compounds, further demonstrating the potential of these novel compounds.

Keywords: Antibacterials ; Bacterial resistance ; Quorum sensing ; Pseudomonas Aeruginosa ; Broad–spectrum ; Dihydropyrrol-2-one

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Product Details of [ 563-96-2 ]

CAS No. :563-96-2 MDL No. :MFCD00127974
Formula : C2H4O4 Boiling Point : -
Linear Structure Formula :- InChI Key :MOOYVEVEDVVKGD-UHFFFAOYSA-N
M.W : 92.05 Pubchem ID :15620607
Synonyms :
Glyoxylic acid monohydrate

Calculated chemistry of [ 563-96-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 15.82
TPSA : 77.76 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.17
Log Po/w (XLOGP3) : -1.42
Log Po/w (WLOGP) : -1.62
Log Po/w (MLOGP) : -1.81
Log Po/w (SILICOS-IT) : -1.3
Consensus Log Po/w : -1.26

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : 0.55
Solubility : 327.0 mg/ml ; 3.55 mol/l
Class : Highly soluble
Log S (Ali) : 0.29
Solubility : 179.0 mg/ml ; 1.95 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 1.94
Solubility : 8040.0 mg/ml ; 87.3 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 563-96-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P234-P261-P264-P272-P280-P302+P352-P305+P351+P338+P310-P333+P313-P390-P406-P501 UN#:3261
Hazard Statements:H290-H315-H317-H318 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 563-96-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 563-96-2 ]

[ 563-96-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 19832-98-5 ]
  • [ 563-96-2 ]
  • [4-Methyl-1-oxo-3,4-dihydro-1H-naphthalen-(2Z)-ylidene]-acetic acid [ No CAS ]
  • [4-Methyl-1-oxo-3,4-dihydro-1H-naphthalen-(2E)-ylidene]-acetic acid [ No CAS ]
  • 2
  • [ 1197040-29-1 ]
  • [ 33332-28-4 ]
  • [ 563-96-2 ]
  • (5-chloro-imidazo[1,2-<i>a</i>]pyrazin-3-yl)-phenyl-amine [ No CAS ]
  • 3
  • [ 1313585-57-7 ]
  • [ 145349-76-4 ]
  • [ 563-96-2 ]
  • [ 1313585-77-1 ]
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