2,4-Dichloro-3-nitro-quinoline

Bezeichnung:2,4-Dichloro-3-nitro-quinoline

CAS-Nr132521-66-5

Englisch Name:2,4-Dichloro-3-nitro-quinoline

CBNumberCB5773772

SummenformelC9H4Cl2N2O2

Molgewicht243.05

MOL-Datei132521-66-5.mol

2,4-Dichloro-3-nitro-quinoline physikalisch-chemischer Eigenschaften

Schmelzpunkt	102 °C(Solv: methanol (67-56-1); ethyl acetate (141-78-6))
Siedepunkt	359.7±37.0 °C(Predicted)
Dichte	1.593±0.06 g/cm3(Predicted)
storage temp.	-20°C Freezer
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	-4.98±0.50(Predicted)
Farbe	White to Off-White
InChI	InChI=1S/C9H4Cl2N2O2/c10-7-5-3-1-2-4-6(5)12-9(11)8(7)13(14)15/h1-4H
InChIKey	RSFJVCHKGRUCIC-UHFFFAOYSA-N
SMILES	N1C2C(=CC=CC=2)C(Cl)=C([N+]([O-])=O)C=1Cl

Sicherheit

HS Code

2933499090

Gefahreninformationscode (GHS)

2,4-Dichloro-3-nitro-quinoline Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
2,4-Dichloro-3-nitroquinoline is a chemotherapeutic drug that belongs to the class of epidermal growth factor receptor (EGFR) inhibitors. This agent has anticancer activity against cells in the G1 phase of the cell cycle and may also have some antiproliferative effects on tumor cells. 2,4-Dichloro-3-nitroquinoline binds to EGFR and inhibits the binding of epidermal growth factor (EGF) to its receptor. This binding causes the activation of downstream signaling pathways that regulate cell proliferation.
Verwenden
2,4-Dichloro-3-nitroquinoline has antitumor activity.
Synthese

15151-57-2

132521-66-5

(2) Synthesis of 2,4-dichloro-3-nitroquinoline: In a 20 mL round-bottomed flask, 3-nitroquinoline-2,4-diol (1 g, 4.85 mmol), phosphorus trichloride (appropriate amount) and N,N-dimethylaniline (0.19 mL) were added sequentially. The reaction mixture was stirred at 90 °C for 2 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature, slowly poured into ice water, and stirring was continued for 0.5 hours. The precipitate precipitated was collected by filtration and dried under vacuum overnight. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=5:1, v/v) to give 0.7 g of white solid product in 59.4% yield.
Einzelnachweise
[1] Medicinal Chemistry Research, 2014, vol. 23, # 6, p. 2964 - 2975
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 11, p. 4450 - 4465
[3] Patent: WO2013/67597, 2013, A1. Location in patent: Page/Page column 78
[4] Patent: WO2018/191746, 2018, A1. Location in patent: Paragraph 0391
[5] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 921 - 926

2,4-Dichloro-3-nitro-quinoline Upstream-Materialien And Downstream Produkte

2,4-Dichloro-3-nitro-quinoline Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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