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

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3d Animation Molecule Structure of 618-46-2
Chemical Structure| 618-46-2
Chemical Structure| 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 : -
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 Ų

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:
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.

  • Upstream synthesis route of [ 618-46-2 ]
  • Downstream synthetic route of [ 618-46-2 ]

[ 618-46-2 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 618-46-2 ]
  • [ 70057-67-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 6761 - 6774
  • 2
  • [ 618-46-2 ]
  • [ 937-14-4 ]
Reference: [1] Journal of applied chemistry of the USSR, 1986, vol. 59, # 2 pt 2, p. 353 - 356
[2] Journal of applied chemistry of the USSR, 1985, vol. 58, # 5 pt 2, p. 1014 - 1017
[3] J. Appl. Chem. USSR (Engl. Transl.), 1988, vol. 61, # 1, p. 118 - 120[4] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1988, vol. 61, # 1, p. 123 - 125
[5] Journal of applied chemistry of the USSR, 1985, vol. 58, # 5 pt 2, p. 1014 - 1017
  • 3
  • [ 618-46-2 ]
  • [ 1673-47-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1368 - 1372
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 192 - 194
[3] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 8, p. 2271 - 2276
[4] Journal of Molecular Structure, 2016, vol. 1117, p. 8 - 16
  • 4
  • [ 63503-60-6 ]
  • [ 618-46-2 ]
  • [ 7094-34-0 ]
YieldReaction ConditionsOperation in experiment
27% With palladium diacetate; sodium carbonate In water at 0 - 80℃; for 1.33333 h; 10182] To a solution of 8-9 (45.3 g, 0.29 mol), Pd (OAc)2 (3.2 g, 14.3 mmol) and Na2CO3 (48 g, 0.46 mol) in PEG:H20 (600 mE, v/v=1:1), was added 8-8 (50.7 g, 0.29 mol) portionwise at 00 C. for 20 mm. The mixture was stirred at 80° C. for 1 h, and then extracted with EtOAc (3x500 mE). The combined organic layers were washed with brine (2x300 mE), dried with Na2SO4 and concentrated to give a residue. The residue was purified by silica gel chromatography (PE:EA=100:1 to 20:1) to provide 8-10 as a white solid (20 g, 27percent). ‘H NMR (400 MHz, CD3C1): ö 7.78 (s, 1H), 7.66 (d, J=7.7 Hz, 1H), 7.60 (d, J=8.2 Hz, 1H), 7.49-7.43 (m, 1H).
Reference: [1] Patent: US2015/72982, 2015, A1, . Location in patent: Paragraph 0181; 0182
  • 5
  • [ 618-46-2 ]
  • [ 63012-03-3 ]
Reference: [1] Journal of Organic Chemistry, 1967, vol. 32, p. 2692 - 2695
  • 6
  • [ 64-17-5 ]
  • [ 618-46-2 ]
  • [ 1128-76-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1857, vol. 102, p. 264
  • 7
  • [ 6638-79-5 ]
  • [ 618-46-2 ]
  • [ 145959-21-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1415 - 1419
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 46, p. 6840 - 6850
[3] Patent: EP579833, 1997, B1,
[4] Patent: WO2011/23677, 2011, A1, . Location in patent: Page/Page column 122
[5] Chemical Communications, 2012, vol. 48, # 71, p. 8976 - 8978
  • 8
  • [ 618-46-2 ]
  • [ 1117-97-1 ]
  • [ 145959-21-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 1, p. 49 - 64
[2] Patent: US2007/270498, 2007, A1, . Location in patent: Page/Page column 7; 8
  • 9
  • [ 618-46-2 ]
  • [ 145959-21-3 ]
YieldReaction ConditionsOperation in experiment
10.6 g With triethylamine In dichloromethane at 20℃; for 2.66667 h; Inert atmosphere; Cooling with ice 10306] To a cooled (ice bath) solution of N-methyl-O-methylhydroxylamine hydrochloride (6.13 1 g, 62.85 mmol) and triethylamine (20 mE, 142.85 mmol) in dry DCM (under Ar atmosphere) was added 3-chlorobenzoyl chloride (7.32 mE, 57.14 mmol) via slow dropwise addition. The mixture was stirred for 10 mins and then warmed to ambient temperature. Afier 2.5 h of stirring, the solvent was partially removed (condense about 80percent-rotary evaporator). The remainder was taken up in EA, washed successively with iN HC1 (twice) and 2M aqueous sodium carbonate, and then diluted a brine solution. The aqueous phases were back-extracted. The organic phases were combined, dried with magnesium sulfate, filtered and concentrated to give E-1 (10.6 g), which was used directly in the next step without thrther purification.
Reference: [1] Patent: US2015/72982, 2015, A1, . Location in patent: Paragraph 0305; 0306
  • 10
  • [ 618-46-2 ]
  • [ 145959-21-3 ]
Reference: [1] Patent: US5686455, 1997, A,
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