Trifluoromethyl alkyl quinoline compounds, synthetic methods and antitumor applications thereof

Abstract

The application discloses a trifluoromethyl alkyl quinoline compound, a synthesis method and anti-tumor application in the field of organic synthesis and medicinal chemistry, which is synthesized from trifluoropropylene quinoline or N-benzoyl pyrrole (A) and redox active ester (B) as raw materials, dimethyl sulfoxide as a solvent, dihydropyridine as an electron donor, and under visible light irradiation, a trifluoromethyl alkyl quinoline and analogues (C) are synthesized at a high yield. The specific reaction formula is as follows: The compounds provided by the application all have excellent anti-tumor activity and low toxicity to normal cells, and therefore have application prospects for preparing anti-tumor drugs.

Description

Technical Field

[0001] The present invention relates to the fields of organic synthesis and medicinal chemistry, and in particular to a trifluoromethylalkyl quinoline compound, a synthesis method and anti-tumor application thereof. Background Art

[0002] Tumors are one of the factors that seriously endanger human health and are currently the second leading cause of morbidity and mortality worldwide. The main anti-tumor treatment methods include surgery, radiotherapy, chemotherapy, immunotherapy, etc. Chemotherapy is one of the most effective means of treating malignant tumors, and cisplatin is a classic chemotherapy drug for liver cancer. Resistance to platinum chemotherapy is a key factor in poor prognosis and recurrence of liver cancer cells. Tumor cells that develop resistance to one chemotherapy drug will rapidly induce acquired tolerance to other chemotherapy drugs, ultimately leading to multidrug resistance. DNA damage repair and circumvention of apoptosis are the main factors that cause tumor cells to develop resistance to platinum drugs. Therefore, developing new drugs or treatment strategies to alleviate or overcome platinum drug resistance in the treatment of liver cancer is a clinical problem that urgently needs to be addressed.

[0003] Utilizing advantageous pharmacophore backbones to construct heterocyclic small molecule pharmacophoric compounds is an economical and effective strategy for new drug synthesis. Quinoline, as a multifunctional pharmacophore, serves as a versatile scaffold in medicinal chemistry and has broad pharmacological applications in anticancer, anti-inflammatory, antibacterial, and antiviral drugs. Therefore, developing more compounds with antitumor properties using the multifunctional quinoline pharmacophore as a backbone is crucial for overcoming the toxicity and drug resistance issues of traditional platinum-based drugs. Summary of the Invention

[0004] In view of the deficiencies of the prior art, the present invention designs a trifluoromethylalkyl quinoline compound and its analogues with high efficiency, low toxicity and good targeting.

[0005] One of the objects of the present invention is to provide a compound represented by the following general formula C or E, a pharmaceutically acceptable salt thereof, a prodrug molecule thereof, a stereoisomer thereof or a tautomer thereof:

[0006]

[0007] Wherein, R1 is hydrogen, C 1-15 Alkyl, C 1-15 Alkoxy, halogen; the number of n is 1, 2 or 3.

[0008] Specifically, the compound of formula C is one selected from the following compounds:

[0009]

[0010] The second object of the present invention is to provide a method for synthesizing the above-mentioned compound. The specific reaction formula is as follows:

[0011]

[0012] Wherein, R1 is hydrogen, C 1-15 Alkyl, C 1-15 Alkoxy, halogen; the number of n is 1, 2 or 3;

[0013] Specifically, trifluoropropylene quinoline or N-benzoyl pyrrole (A) and redox-active ester (B) are used as raw materials, dimethyl sulfoxide is used as solvent, and dihydropyridine is used as electron donor. Trifluoromethyl alkyl quinoline and its analogues (C) are synthesized in high yield under visible light irradiation.

[0014] Furthermore, the molar ratio of the compound of formula A to the compound of formula B is 1:1 to 3, preferably 1:2.

[0015] Furthermore, the compound of formula A and the compound of formula B are selected from the following groups:

[0016]

[0017] Furthermore, the reaction is carried out at 0-50°C, preferably 30°C.

[0018] Furthermore, the visible light is blue light, and the wavelength is preferably 430 to 490 nm.

[0019] A fourth object of the present invention is to provide the use of the compound, its pharmaceutically acceptable salt, its prodrug molecule, its stereoisomer or its tautomer in the preparation of anti-tumor drugs.

[0020] Furthermore, the tumor is liver cancer or lung cancer.

[0021] The working principle and beneficial effects of the present invention: The synthesis method of the present invention is simple, can react under light conditions and at 0-50°C, is economical, efficient and short in time, and has a yield of up to 98%. Activity tests have confirmed that the synthesized compounds have significant anti-tumor activity and very low toxicity to normal cells, especially compounds C-1, C-4, and C-5, which have application in the preparation of anti-liver cancer drugs and have great development value.

[0022] Terminology: As used herein, the term "C 1-15 The term "alkyl" refers to a straight or branched chain alkyl group having 1 to 15 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or the like.

[0023] The term "C 1-15"Alkoxy" refers to a straight or branched chain alkoxy group having from 1 to 15 carbon atoms, for example methoxy, ethoxy, propyloxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, t-butoxy or the like.

[0024] The term "halogen" refers to fluorine, chlorine, bromine or iodine. DETAILED DESCRIPTION

[0025] The application is further illustrated in detail by the following specific embodiments:

[0026] The present application provides a synthesis of quinoline structure of trifluoromethyl alkyl and its anti-tumor application, as follows:

[0027] The trifluoromethyl alkyl quinoline and its analogues (C) are synthesized in high yield from trifluoropropylene quinoline or N-benzoyl pyrrole (A) and redox active ester (B) as raw materials, dimethyl sulfoxide as solvent, dihydropyridine as electron donor under visible light irradiation.

[0028] The specific reaction formula is as follows:

[0029]

[0030] In the above reaction formula, R1, n are defined as described above.

[0031] In the reaction formula, compounds A, B are selected from the following group of compounds:

[0032]

[0033] The compound of formula A and the compound of formula B can be prepared by commercially available or methods well known to those skilled in the art, however, the specific conditions of the method, such as reactants, solvents, the amount of compounds used, reaction temperature, reaction time required, etc. are not limited to the following explanation.

[0034] The compound of formula C prepared by the present application can be further modified as needed to prepare various functional compounds.

[0035] The product prepared by the preparation method of the present application can be separated and purified by various methods, including recrystallization, column chromatography, etc. The above purification methods are all conventional methods in the art, for example, when recrystallization is carried out, mixed solvents of polar solvents and non-polar solvents can be used, preferably ethyl acetate-petroleum ether, ethanol-petroleum ether and the like. When column chromatography is used, the developing agent used can be a single solvent or a mixed solvent, for example, petroleum ether or ethyl acetate-petroleum ether and the like.

[0036] The present invention will be further described below in conjunction with specific implementation. It should be understood that these examples are intended to illustrate the present invention only and are not intended to limit the scope of the present invention. The experimental methods in the following examples, for which specific conditions are not specified, are generally based on conventional conditions or the conditions recommended by the manufacturer. Unless otherwise stated, percentages and parts are calculated by weight.

[0037] In the following examples, conventional post-treatment methods in the art were used for purification.

[0038] Example 1

[0039]

[0040] To a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-1 (44.6 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 12 h gave compound C-1 in a 77% yield. 1 H NMR (400MHz, CDCl3) δ8.18(d,J=8.8Hz,1H),8.11(d,J=8.4Hz,1H),7.83(d,J=8.4Hz,1H),7.73(t,J=7.2Hz,1H),7.56(t,J=7.2Hz, 1H),7.44(d,J=8.4Hz,1H),4.51(s,1H),3.80–3.68(m,1H),3.06–2.96(m,2H),2.20–2.02(m,2H),1.41(s,9H),1.39–1.11(m,6H).

[0041] Example 2

[0042]

[0043] To a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-2 (44.6 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 12 h gave compound C-2 in a 98% yield. 1H NMR (400MHz, CDCl3) δ8.80(d,J=2.0Hz,1H),8.12(d,J=8.4Hz,1H),8.08(s,1H),7.82(d,J=8.0Hz,1H),7.75–7.69(m,1H),7.56(t,J=7. 2Hz,1H),4.59(s,1H),3.49–3.37(m,1H),3.02(q,J=6.4Hz,2H),2.15–2.05(m,1H),2.04–1.92(m,1H),1.39(s,9H),1.36–1.10(m,6H).

[0044] Example 3

[0045]

[0046] To a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-3 (44.6 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 24 h gave compound C-3 in a 58% yield. 1 H NMR (400MHz, CDCl3) δ8.96(bs,1H),8.41(d,J=8.8Hz,1H),8.16(d,J=8.4Hz,1H),7.77(t,J=7.8Hz,1H),7.66(d,J=7.2Hz,1H),7.53–7 .49(m,1H),4.44(s,1H),4.21–4.07(m,1H),3.05–2.97(m,2H),2.25–2.15(m,1H),2.11–2.01(m,1H),1.41(s,9H),1.38–1.10(m,6H).

[0047] Example 4

[0048]

[0049] To a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-4 (44.6 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 12 h gave compound C-4 in a 68% yield.1 H NMR (400MHz, CDCl3) δ8.95(bs,1H),8.39(d,J=8.8Hz,1H),8.14(d,J=8.4Hz,1H),7.76(t,J=7.8Hz,1H),7.65(d,J=7.2Hz,1H),7.51–7. 46(m,1H),4.48(s,1H),4.22–4.08(m,1H),3.00(q,J=6.8Hz,2H),2.24–2.14(m,1H),2.12–2.01(m,1H),1.40(s,9H),1.38–1.10(m,6H).

[0050] Example 5

[0051]

[0052] To a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-5 (44.6 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 12 h gave compound C-5 in an 88% yield. 1 H NMR (400MHz, CDCl3) δ8.89(dd,J=4.4Hz,1.6Hz,1H),8.14(d,J=8.4Hz,1H),8.11(d,J=8.8Hz,1H),7.70(s,1H),7.62(d,J=8.8Hz,1H),7.40(dd, J=8.4Hz,4.4Hz,1H),4.60(bs,1H),3.45–3.33(m,1H),3.04–2.97(m,2H ),2.10–2.00(m,1H),1.99–1.89(m,1H),1.38(s,9H),1.36–1.07(m,6H).

[0053] Example 6

[0054]

[0055] Into a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.), Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.), DMSO (2.0 mL) and A-6 (44.6 mg, 0.2 mmol) were added after purging with argon for three times. After stirring at 30 °C for 12 h under blue light (430-490 nm) irradiation, compound C-6 was obtained in 98% yield. 1 H NMR (400 MHz, CDC13) δ 8.93 (d, J = 2.0 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H), 8.04 (s, 1H), 7.83 (d, J = 8.4 Hz, 1H), 7.48 (d, J = 8.8 Hz, 1H), 7.43 (dd, J = 8.4 Hz, 4.0 Hz, 1H), 4.49 (s, 1H), 3.50 - 3.39 (m, 1H), 3.02 (q, J = 6.0 Hz, 2H), 2.12 - 1.94 (m, 2H), 1.40 (s, 9H), 1.37 - 1.15 (m, 6H).

[0056] Example 7

[0057]

[0058] Into a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.), Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.), DMSO (2.0 mL) and A-7 (47.4 mg, 0.2 mmol) were added after purging with argon for three times. After stirring at 30 °C for 12 h under blue light (430-490 nm) irradiation, compound C-7 was obtained in 65% yield. 1 H NMR (400 MHz, CDC13) δ 8.93 (d, J = 2.0 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H), 8.04 (s, 1H), 7.83 (d, J = 8.4 Hz, 1H), 7.48 (d, J = 8.8 Hz, 1H), 7.43 (dd, J = 8.4 Hz, 4.0 Hz, 1H), 4.49 (s, 1H), 3.50 - 3.39 (m, 1H), 3.02 (q, J = 6.0 Hz, 2H), 2.12 - 1.94 (m, 2H), 1.40 (s, 9H), 1.37 - 1.15 (m, 6H).

[0059] Example 8

[0060]

[0061] To a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-8 (47.4 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 24 h gave compound C-8 in a 68% yield. 1 H NMR (400MHz, CDCl3) δ8.10(d,J=8.0Hz,1H),7.99(d,J=8.4Hz,1H),7.72(t,J=7.6Hz,1H),7.57(t,J=7.6Hz,1H),7.26(s, 1H),4.51(s,1H),3.74–3.62(m,1H),3.06–2.97(m,2H),2.72(s,3H),2.18–2.01(m,2H),1.41(s,9H),1.38–1.12(m,6H).

[0062] Example 9

[0063]

[0064] To a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-9 (50.6 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 12 h gave compound C-9 in a 98% yield. 1 H NMR (400MHz, CDCl3) δ8.14(d,J=8.8Hz,1H),7.51–7.43(m,2H),7.38(d,J=8.0Hz,1H),7.07(d,J=8.0Hz,1H),4.5 3(s,1H),4.07(s,3H),4.00–3.87(m,1H),3.06–2.94(m,2H),2.14–1.95(m,2H),1.40(s,9H),1.39–1.10(m,6H).

[0065] Example 10

[0066]

[0067] To a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-10 (58.2 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 24 h gave compound C-10 in a 52% yield. 1 H NMR (400MHz, CDCl3) δ8.21(d,J=8.4Hz,1H),8.15(d,J=8.4Hz,1H),7.84(t,J=7.6Hz,1H),7.72(t,J=8.0Hz,1H),7 .69(s,1H),4.48(s,1H),3.84–3.73(m,1H),3.09–3.00(m,2H),2.25–2.04(m,2H),1.41(s,9H),1.45–1.15(m,6H).

[0068] Example 11

[0069]

[0070] To a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-11 (48.2 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 12 h gave compound C-11 in a 98% yield. 1 H NMR (400MHz, CDCl3) δ8.12(d,J=8.4Hz,1H),8.09(dd,J=9.2Hz,5.2Hz,1H),7.53–7.46(m,1H),7.43(d,J=8.8H z,2H),4.52(s,1H),3.76–3.65(m,1H),3.06–2.98(m,2H),2.20–2.01(m,2H),1.41(s,9H),1.40–1.06(m,6H).

[0071] Example 12

[0072]

[0073] To a 25 mL reaction tube, compound B-1 (145.0 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-12 (53.9 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 12 h gave compound C-12 in a 98% yield. 1 H NMR(400MHz, CDCl3)δ7.51(d,J=8.0Hz,2H),7.30(d,J=7.6Hz,2H),4.48(s,1H),3.70–3.36(m, 4H),3.28–3.16(m,1H),3.08–3.00(m,2H),2.03–1.79(m,6H),1.42(s,9H),1.40–1.10(m,6H).

[0074] Example 13

[0075]

[0076] To a 25 mL reaction tube, compound B-2 (150.6 mg, 0.4 mmol, 2.0 equiv.) and Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added. After purging the atmosphere with argon three times, DMSO (2.0 mL) and A-5 (44.6 mg, 0.2 mmol) were added. Under blue light (430-490 nm), stirring at 30°C for 12 h gave compound C-13 in a 53% yield. 1 H NMR (400MHz, CDCl3) δ8.94(d,J=2.8Hz,1H),8.20(d,J=8.4Hz,1H),8.17(d,J =9.2Hz,1H),7.74(s,1H),7.67(d,J=8.8Hz,1H),7.47(q,J=4.0Hz,1H),4.44( s,1H),3.49–3.37(m,1H),3.08–2.96(m,2H),2.16–2.06(m,1H),2.04–1.94( m,1H),1.56–1.42(m,2H),1.37(s,9H),1.30–1.14(m,5H),0.95–0.83(m,1H).

[0077] Example 14

[0078]

[0079] Into a 25 mL reaction tube, compound B-3 (139.3 mg, 0.4 mmol, 2.0 equiv.), Hantzschester (152.0 mg, 0.6 mmol, 3.0 equiv.) were added, and DMSO (2.0 mL) and A-5 (44.6 mg, 0.2 mmol) were added after three times of argon replacement. After stirring at 30°C for 12 h under blue light (430-490 nm) irradiation, compound C-14 was obtained in a yield of 57%. 1 H NMR (400 MHz, CDC13) δ 8.94 (dd, J = 4.4 Hz, 2.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), 8.16 (d, J = 8.8 Hz, 1H), 7.74 (s, 1H), 7.66 (d, J = 8.8 Hz, 1H), 7.46 (d, J = 8.4 Hz, 4.4 Hz, 1H), 4.44 (s, 1H), 3.49 - 3.36 (m, 1H), 3.08 - 2.97 (m, 2H), 2.16 - 1.94 (m, 2H), 1.57 - 1.41 (m, 2H), 1.37 (s, 9H), 1.27 - 1.14 (m, 2H).

[0080] Activity test of trifluoromethylalkyl quinoline and analogs thereof

[0081] Cell lines and solvents

[0082] Human hepatoma Huh-7 cells;

[0083] Human lung cancer A549 cells;

[0084] The cells were cultured in RPMI1640 medium containing 10% fetal bovine serum;

[0085] Solvent: dimethyl sulfoxide (abbreviated as DMSO).

[0086] Embodiment for detecting cell anti-tumor activity by CCK-8 staining method

[0087] Cells with a tumor activity ratio of more than 90% were selected for the experiment. The cell proliferation inhibition test used EnoGene CellTM Counting Kit-8 (abbreviated as CCK-8) cell viability detection kit. The logarithmic growth period of human hepatoma Huh-7 cells and human lung cancer A549 cells was taken, the culture medium was discarded, PBS was washed twice, trypsin was digested, centrifuged, the culture medium was resuspended and mixed with the cells, 5 x 10 4Each well was inoculated in parallel in a 96-well plate. The 96-well plate was placed in a 37°C, 5% CO2 incubator for 8 hours and then taken out. 4 μM of the culture medium of the test compound was added to each well. A negative control group, a vehicle control group, and a positive control group (the positive controls were sorafenib and cisplatin, respectively) were set up at the same time. Each group was repeated 3 times. After continuing to culture in a 37°C, 5% CO2 incubator for 48 hours, 10 μL of CCK-8 solution was added to each well. After incubating the culture plate in the incubator, the absorbance (OD value) at 450 nm was measured using a microplate reader. The experimental group and the control group were repeated 3 times to calculate the proliferation inhibition rate of each compound on human liver cancer cells Huh-7 and human lung cells A549. The experimental results are shown in Table 1.

[0088] Table 1: Inhibition rate of proliferation of human liver cancer Huh-7 cells

[0089] Compound Huh-7 inhibition rate (%) C-1 67 C-2 37 C-3 34 C-4 57 C-5 66 C-6 41 C-7 42 C-8 48 C-9 46 C-10 45 C-11 46 C-12 30 C-13 40 C-14 30 Sorafenib 30

[0090] Table 2: Inhibition rate of proliferation of human lung cancer A549 cells

[0091]

[0092]

[0093] The experimental results in Table 1 show that Compound C-1, Compound C-2, Compound C-3, Compound C-4, Compound C-5, Compound C-6, Compound C-7, Compound C-8, Compound C-9, Compound C-10, Compound C-11, Compound C-12, Compound C-13, and Compound C-14 of the present invention have significant in vitro anti-tumor activity, and have significant inhibitory activity against human liver cancer cells Huh-7. The experimental results in Table 2 show that Compound C-2, Compound C-4, Compound C-7, and Compound C-9 have significant inhibitory activity against human lung cancer cells A549. Therefore, the above compounds are suitable anti-tumor drug candidates.

[0094] The above is only an embodiment of the present invention, and the common knowledge such as the specific structure and characteristics of the scheme is not described in detail here. It should be pointed out that for those skilled in the art, without departing from the structure of the present invention, several variations and improvements can be made, which should also be regarded as the scope of protection of the present invention, and these will not affect the effect of the implementation of the present invention and the practicality of the patent. The scope of protection required by this application shall be based on the content of its claims, and the specific implementation methods and other records in the specification can be used to interpret the content of the claims.

Claims

1. A compound represented by the following general formula C, or a pharmaceutically acceptable salt thereof: ， in, When R1 is hydrogen, the number of n is 1 or 2; or R1 is C 1-15 Alkyl, C 1-15 Alkoxy, halogen; the number of n is 1, 2 or 3.

2. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, characterized in that: The compound of formula C is one selected from the following compounds: 。 3. The method for synthesizing the compound according to claim 1, wherein: The specific reaction formula is as follows: ， Wherein, when R1 is hydrogen, the number of n is 1 or 2; or when R1 is C 1-15 Alkyl, C 1-15 Alkoxy, halogen; the number of n is 1, 2 or 3; Specifically, trifluoropropylenequinoline or N-benzoylpyrrole (A) and redox-active ester (B) are used as raw materials, dimethyl sulfoxide is used as solvent, and dihydropyridine is used as electron donor to synthesize trifluoromethylalkylquinoline and its analogues (C) under visible light irradiation.

4. The synthesis method according to claim 3, wherein: The molar ratio of the compound of formula A to the compound of formula B is 1:1-3.

5. The synthesis method according to claim 3 or 4, characterized in that: The reaction is carried out at 0-50°C.

6. The synthesis method according to claim 5, characterized in that: Visible light is blue light.

7. Use of the compound according to claim 1 or 2 or a pharmaceutically acceptable salt thereof in the preparation of anti-tumor drugs.

8. The use according to claim 7, characterized in that: The tumor is liver cancer or lung cancer.

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