Description
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.
Synthesis
(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.
References
[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
