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Chemical Structure| 34893-92-0 Chemical Structure| 34893-92-0

Structure of 34893-92-0

Chemical Structure| 34893-92-0

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Product Citations

Product Citations

Faisal Aziz ; Kanamata Reddy ; Virneliz Fernandez Vega ; Raja Dey ; Katherine A. Hicks ; Sumitha Rao , et al.

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 [ 34893-92-0 ]

CAS No. :34893-92-0
Formula : C7H3Cl2NO
M.W : 188.01
SMILES Code : ClC1=CC(Cl)=CC(N=C=O)=C1
MDL No. :MFCD00013859
InChI Key :XEFUJGURFLOFAN-UHFFFAOYSA-N
Pubchem ID :94460

Safety of [ 34893-92-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311+H331-H315-H319-H335
Precautionary Statements:P261-P280-P301+P310-P305+P351+P338-P311
Class:6.1
UN#:2206
Packing Group:

Application In Synthesis of [ 34893-92-0 ]

* 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 [ 34893-92-0 ]

[ 34893-92-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 117011-70-8 ]
  • [ 34893-92-0 ]
  • [ 121809-80-1 ]
  • 2
  • [ 117011-70-8 ]
  • [ 34893-92-0 ]
  • 2-(4-(3,5-dichlorophenylureido)phenoxy)-2-methyl-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
This compound is reacted with 3,5-dichlorophenyl isocyanate to form 2(4(3,5 -dichlorophenylureido)phenoxy)2-methylpropionic acid.
1.81 g (94%) In pyridine; water; EXAMPLE 4 2-(4-(3,5-Dichlorophenylureido)phenoxy)-2-methylpropionic acid To a stirring solution of 4.95 g (0.025 mole) of <strong>[117011-70-8]2-(4-aminophenoxy)-2-methylpropionic acid</strong> in 50 ml dry pyridine, 4.95 g (0.025 mole) of 3,5-dichlorophenyl isocyanate were added. After 1 hour stirring at room temperature, 150 ml water was added and the mixture was acidified with concentrated HCl. The precipitate was filtered, washed several times with cold water and dried. Recrystallization from aqueous acetone gave small plates 1.81 g (94%) MP 182-184.
  • 3
  • [ 773-76-2 ]
  • [ 34893-92-0 ]
  • [ 1221161-38-1 ]
YieldReaction ConditionsOperation in experiment
58% With triethylamine; In diethyl ether; at 20℃; for 48h; Example 4. General Procedure for the Synthesis of 8-Quinolyl CarbamatesTriethylamine (3 drops) was added to a suspension of 8-hydroxyquinoline (1 mmol) and an isocyanate (1 mmol) in diethyl ether (15 mL). The reaction mixture was stirred for 2 days at room temperature and the solvent was removed using a rotary evaporator and the residue was subjected to flash- column chromatography over silica gel (eluent: hexanes or 5% EtOAc in hexanes) to afford the respective quinolyl carbamate.5,7-Dichloro-8-quinoIyl-iV-(3,5-dichlorophenyl)-carbamate (4b) Yield: 233 mg, 58% Analytical data for 4b: Rf 0.64 (7:3 hexanes-EtOAc) mp. 148 0C1H NMR (400 MHz, CDCl3) delta: 10.56 (br s, IH, NH); 8.68 (dd, 7=4.4, 1.6 Hz, IH, H-2); 8.52 (dd, J=8.8, 1.5 Hz, IH, H-4); 7.62 (s, IH, H-6); 7.59 (dd, J=8.8, 4.4 Hz, IH, H-3); 7.12 (app. t, 7=2.0 Hz, 2H, 2,6-aniline); 7.18 (d, J=2.0 Hz, IH, 4-aniline)'3C NMR (100 MHz, CDCl3) delta: 154.62, 152.44, 149.81, 140.74, 136.15, 135.53, 132.78, 131.33, 128.56, 126.27, 122.30, 121.98, 121.87, 118.52MS (MALDI-TOF) m/z : 403
  • 4
  • [ 63746-12-3 ]
  • [ 34893-92-0 ]
  • C16H10Cl2N2O4 [ No CAS ]
 

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