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[ CAS No. 5271-67-0 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 5271-67-0
Chemical Structure| 5271-67-0
Structure of 5271-67-0 * Storage: {[proInfo.prStorage]}

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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 [ 5271-67-0 ]

CAS No. :5271-67-0 MDL No. :MFCD00005428
Formula : C5H3ClOS Boiling Point : -
Linear Structure Formula :C4H3SC(O)Cl InChI Key :QIQITDHWZYEEPA-UHFFFAOYSA-N
M.W : 146.59 Pubchem ID :78928
Synonyms :

Calculated chemistry of [ 5271-67-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.5
TPSA : 45.31 ?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) : -5.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 2.55
Log Po/w (WLOGP) : 2.13
Log Po/w (MLOGP) : 1.01
Log Po/w (SILICOS-IT) : 3.06
Consensus Log Po/w : 2.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.75
Solubility : 0.26 mg/ml ; 0.00177 mol/l
Class : Soluble
Log S (Ali) : -3.15
Solubility : 0.104 mg/ml ; 0.00071 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.21
Solubility : 0.906 mg/ml ; 0.00618 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 5271-67-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H227-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 5271-67-0 ]

* 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 [ 5271-67-0 ]

[ 5271-67-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 188290-36-0 ]
  • [ 5271-67-0 ]
  • [ 704-38-1 ]
YieldReaction ConditionsOperation in experiment
70% With copper(II) ferrite; In neat (no solvent); at 80℃; for 24h; General procedure: The FC acylation of various benzenes with acid chlorides was carried out in the presence of magnetic nano CuFe2O4 (particle size = 50 nm) by using one of the reaction condition (A-D) given below. Condition A: Anisole/arene (1 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), 1,2-DCE (2 mL), 80 C and 24 h. Condition B: Anisole/arene (1 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), 1,2-DCE (2 mL), rt (35-38 C) and 18 h. Condition C: Neat reaction, anisole/arene (3.3 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), rt (35-38 C) and 18 h. Condition D: Neat reaction, arene/anisole (3.3 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), 80 C and 18 h.
  • 2
  • [ 5835-79-0 ]
  • [ 5271-67-0 ]
  • thiophene-2-carboxylic acid-(4-morpholino-butyl ester); hydrochloride [ No CAS ]
  • 3
  • [ 5918-93-4 ]
  • [ 5271-67-0 ]
  • [ 77681-44-8 ]
YieldReaction ConditionsOperation in experiment
aluminium trichloride; In nitrobenzene; EXAMPLE 13 1,3-Dihydro-4-(2-thienoyl)-2H-imidazol-2-one In 50 ml of nitrobenzene is combined 13.3 g of aluminum chloride, 4.2 g of 1,3-dihydro-2H-imidazol-2-one and 8.1 g of thienoyl chloride. The mixture is stirred at 60° C. for 3 hours and poured over ice water. The solids are filtered, washed with ether and recrystallized twice from ethanol-water to afford the title compound. M.P. 339°-42° C.
  • 4
  • [ 5271-67-0 ]
  • [ 7579-20-6 ]
  • 2-thiophen-2-yl-pyrido[3,4-<i>d</i>][1,3]oxazin-4-one [ No CAS ]
  • 5
  • [ 5271-67-0 ]
  • [ 718632-46-3 ]
  • [ 1041015-87-5 ]
  • 6
  • [ 5271-67-0 ]
  • [ 21109-25-1 ]
  • C14H12N2OS [ No CAS ]
  • 7
  • [ 5271-67-0 ]
  • [ 5234-86-6 ]
  • [ 1215603-73-8 ]
YieldReaction ConditionsOperation in experiment
44% In dichloromethane; at 0 - 20℃;Inert atmosphere; General procedure: To a stirred solution of compound 16 (500 mg, 2.7 mmol) in DCM (50 mL), cyclohexanecarbonyl chloride (532 L, 4.0 mmol) was added at 0 C. The mixture was stirred at room temperature overnight. The reaction was quenched with NaHCO3 (aq.), extracted with DCM (50 mL × 3). The organic phases were then processed in the usual way and chromatographed (1:1 petroleum ether/ EtOAc) to afforded compound 19 (350 mg, 43%) as white solid.
  • 8
  • [ 5271-67-0 ]
  • [ 17701-61-0 ]
  • [ 1379613-69-0 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In dichloromethane; for 2h;Cooling with ice; Reference Example 2 3-(Benzyloxy)-2,2-dimethyl-3-oxopropylthiophene-2-carboxylate [0395] [0396] The compound (2.0 g) produced in Reference Example 1 was dissolved in dichloromethane (30 mL). To this solution, triethylamine (2.7 mL) was added, and then, 2-thiophenecarboxylic acid chloride (1.5 mL) was added thereto under ice-cooling. The resulting solution was stirred for 2 hours under ice-cooling. To the reaction mixture, a saturated aqueous solution of sodium carbonate (30 mL) was added, and then, extraction was performed with ethyl acetate (100 mL×2). The organic layers were combined, and washed with a saturated aqueous solution of sodium chloride (30 mL), and then dried over magnesium sulfate. After magnesium sulfate was removed by filtration, the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (a medium-pressure preparative liquid chromatograph, W-prep 2XY manufactured by Yamazen Corporation (column: main column 2L, inject column L, n-hexane:ethyl acetate=1:0-8:2 (gradient time: 15 minutes), fractionation mode GR), whereby the title compound (3.0 g, 100%) having the following physical properties was obtained. [0397] TLC (Rf value): 0.65 (n-hexane:ethyl acetate=3:1) [0398] NMR (CDCl3): delta 7.67-7.69 (m, 1H), 7.52-7.55 (m, 1H), 7.26-7.34 (m, 5H), 7.05-7.08 (m, 1H), 5.16 (s, 2H), 4.34 (s, 2H), 1.28 (s, 6H)
  • 9
  • [ 5271-67-0 ]
  • [ 22259-53-6 ]
  • [ 1327694-62-1 ]
  • 10
  • [ 5271-67-0 ]
  • [ 108565-42-0 ]
  • [ 704-38-1 ]
YieldReaction ConditionsOperation in experiment
95% With iron(III) chloride; In 1,2-dichloro-ethane; at 80℃; for 1h;Inert atmosphere; General procedure: A mixture of tris(2-thienyl)stibane (370 mg, 1.00 mmol), benzoyl chloride (422 mg, 3.00 mmol), and FeCl3 (16.2 mg, 0.10 mmol) in 1,2-dichloroethane (DCE) (3 mL)was stirred for 1 h at 80 C under an argon atmosphere. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography using hexane/EtOAc (10:1) as eluent to afford 541 mg (96% yield) of 3aa as a yellow oil. Recrystallization from hexane/Et2O gave yellow needle crystals:
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