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[ CAS No. 618-46-2 ] {[proInfo.proName]}

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Chemical Structure| 618-46-2
Chemical Structure| 618-46-2
Structure of 618-46-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 618-46-2 ]

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Product Citations

Product Citations

Faisal Aziz ; Kanamata Reddy ; Virneliz Fernandez Vega , et al. DOI:

Abstract: The suppressor of T cell receptor signaling (Sts) proteins are negative regulators of immune signaling. Genetic inactivation of these proteins leads to significant resistance to infection. From a 590,000 compound high-throughput screen, we identified the 2-(1H)-quinolinone derivative, , as a putative inhibitor of Sts activity. , and a small library of derivatives, are competitive, selective inhibitors of Sts-1 with IC50 values from low to submicromolar. SAR analysis indicates that the , the acid, and the moieties are all essential for activity. A crystal structure confirmed the SAR and reveals key interactions between this class of compound and the . Although has poor cell permeability, we demonstrated that a liposomal preparation can inactivate the activity of Sts-1 in cells. These studies demonstrate that Sts-1 enzyme activity can be pharmacologically inactivated and provide foundational tools and insights for the development of immune-enhancing therapies that target the Sts proteins.

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Product Details of [ 618-46-2 ]

CAS No. :618-46-2 MDL No. :MFCD00000671
Formula : C7H4Cl2O Boiling Point : No data available
Linear Structure Formula :- InChI Key :WHIHIKVIWVIIER-UHFFFAOYSA-N
M.W : 175.01 Pubchem ID :69252
Synonyms :

Calculated chemistry of [ 618-46-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.64
TPSA : 17.07 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 3.66
Log Po/w (WLOGP) : 2.72
Log Po/w (MLOGP) : 2.63
Log Po/w (SILICOS-IT) : 2.98
Consensus Log Po/w : 2.79

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.61
Solubility : 0.0431 mg/ml ; 0.000246 mol/l
Class : Soluble
Log S (Ali) : -3.71
Solubility : 0.0343 mg/ml ; 0.000196 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.57
Solubility : 0.0467 mg/ml ; 0.000267 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.17

Safety of [ 618-46-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314-H335 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 618-46-2 ]

* 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 [ 618-46-2 ]

[ 618-46-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 67198-21-4 ]
  • [ 618-46-2 ]
  • 3-Chloro-N-((1S,2S)-2-dimethylamino-cyclohexyl)-benzamide [ No CAS ]
  • 2
  • [ 7037-49-2 ]
  • [ 618-46-2 ]
  • [ 89-61-2 ]
  • [ 1314530-85-2 ]
YieldReaction ConditionsOperation in experiment
39% A mixture of 1.00 g (5.21 mmol) of 2,5-dichloronitrobenzene and 1.01 g (7.81 mmol) of 4-piperdineethanol in N,N-dimethylformamide (3 mL) is heated at 130 °C and stirred overnight. The mxiture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined organic phase is washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a red oil. The residue is dissolved in ethanol (15 mL) and 0.20 g (0.19 mmol) of 10percent palladium on carbon is added followed by a drop of concentrated hydrochloric acid. The mixture is stirred at room temperature for 2 hours then filtered through a pad of diatomaceous earth and the filter pad is washed with methanol. The mixture is concentrated under reduced pressure to provide a black oil. The residue is disolved in acetonitrile (50 mL) and treated with 1.03 g (5.89 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred at room temperature for 3 hours then concentrated under reduced pressure. To the residue is slowly added a 2M solution of sodium bicarbonate. The mixture is extracted with ethyl acetate and the combined organic phase is washed with brine and dried over anhydrous sodium sulfate. The mixture is concentrated and the residue is purified by flash silica gel chromatography to give 0.800 g (39.0percent overall) of 3-chloro-N-{5-chloro-2-[4-(2- hydroxy-ethyl)-piperidin-l-yl] -phenyl }-benzamide as a brown foam.
  • 3
  • [ 116668-47-4 ]
  • [ 618-46-2 ]
  • C18H12ClNO3 [ No CAS ]
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