Quinoxaline compound and application thereof

Abstract

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a quinoxaline compound and application thereof. The quinoxaline compound provided by the invention is a compound as shown in a formula I or a pharmaceutically acceptable salt thereof. The quinoxaline compound disclosed by the invention is novel in skeleton, and tests prove that the compound has good inhibitory activity on LSD1 and also has relatively good inhibitory activity on gastric cancer cells. Therefore, the quinoxaline compound shows good drug development potential, can provide molecular basis and data support for research and development of drugs for targeted inhibition of LSD1 or anti-gastric cancer drugs, and can also provide potential lead compounds for development of drugs for targeted inhibition of LSD1 and anti-gastric cancer drugs.

Description

Technical Field

[0001] This invention belongs to the field of medicinal chemistry technology, and more specifically relates to a quinoxaline compound and its applications. Background Technology

[0002] Epigenetic modifications play an irreplaceable role in maintaining normal physiological functions and stable gene expression. Processes such as DNA methylation, histone modification, and post-translational modifications collectively drive epigenetic variations. These variations play crucial roles in remodeling chromatin structure and regulating gene activity by activating or inhibiting regulatory molecules. Numerous studies have confirmed that epigenetic alterations, represented by histone modifications, are closely related to the development and progression of various cancers.

[0003] Histone lysine demethylase 1 (LSD1), the first histone demethylase discovered, uses flavin adenine dinucleotide (FAD) as a cofactor to catalyze the demethylation of H3K4me1 / 2 and H3K9me1 / 2 through amine oxidation, thereby affecting the transcription process of related genes.

[0004] Clinical research data shows that LSD1 is highly expressed in gastrointestinal tumors such as gastric cancer. It primarily promotes tumor proliferation, invasion, and metastasis by activating oncogene expression or inhibiting tumor suppressor gene activity. Existing literature has confirmed that inhibiting LSD1 activity can effectively suppress the growth of various gastric cancer cells, making LSD1 a highly promising therapeutic target for gastric cancer.

[0005] In light of this, the development of drugs that specifically target and inhibit LSD1 has become a cutting-edge direction in the field of gastric cancer drug development. Furthermore, in-depth research into the molecular mechanisms of LSD1 in the development and progression of gastric cancer, and accelerating the development of novel LSD1-targeted drugs, has significant clinical value for improving the treatment of gastric cancer. Summary of the Invention

[0006] To overcome the shortcomings of existing technologies, the present invention aims to provide a quinoxaline compound and its applications. The quinoxaline compound provided by the present invention exhibits good inhibitory activity against LSD1 and can also inhibit the activity of gastric cancer cells, thus providing a novel structural framework for the development of drugs targeting LSD1 inhibition or anti-gastric cancer drugs.

[0007] To achieve the above objectives, the technical solution adopted by the present invention is as follows: A quinoxaline compound, which is a compound of formula I or a pharmaceutically acceptable salt thereof: .

[0008] In Formula I, X is selected from one of -, O, NH, NH-NH, NH-CH2, and N(CH3)-CH2; R1 is selected from One of them; R2 is selected from One of them; R3 is selected from one of H, 6,7-CH3, 6,7-F, 6,7-Cl, 6-Cl, 7-OCH3, and 7-COOCH3.

[0009] To improve the inhibitory activity of quinoxaline compounds targeting LSD1, in a preferred embodiment, the quinoxaline compound is selected from compounds with the following structures or pharmaceutically acceptable salts thereof: .

[0010] Furthermore, when X is "-", it indicates that R1 is directly connected at position 3 of the quinoxaline parent ring, without any other atoms or groups in between.

[0011] In a preferred embodiment, the pharmaceutically acceptable salt is one of hydrochloride, sulfate, and nitrate.

[0012] An application of the quinoxaline compound as described above, wherein the application is the use of the quinoxaline compound in the preparation of a drug targeting and inhibiting LSD1; or the application is the use of the quinoxaline compound in the preparation of an antitumor drug.

[0013] In a preferred embodiment, the antitumor drug is an anti-gastric cancer drug.

[0014] In a preferred embodiment, the anti-gastric cancer drug is a drug that inhibits the activity of gastric cancer cells.

[0015] In a preferred embodiment, the gastric cancer cells are HGC-27 cells.

[0016] The beneficial effects of the above-mentioned technical solution of the present invention are as follows: The quinoxaline compounds provided by this invention have a novel skeleton, and experiments have confirmed that this type of compound has good inhibitory activity against LSD1 and also has good inhibitory activity against gastric cancer cells. Therefore, it can provide a novel structural skeleton for the development of highly effective LSD1-targeted inhibitory drugs or anti-tumor drugs.

[0017] This invention relates to the study of quinoxaline compounds, which show good drug development potential. They can provide a molecular basis and data support for the development of drugs that target LSD1 or anti-gastric cancer drugs, and can also provide potential lead compounds for the development of drugs that target LSD1 and anti-gastric cancer drugs. Detailed Implementation

[0018] The present invention is further described below with reference to embodiments, but these are for illustrative purposes only and are not intended to limit the scope of the invention.

[0019] In Examples 1-88 below, the quinoxaline compounds all satisfy the following general formula I: .

[0020] The quinoxaline compounds provided in Examples 1-88 below are designated as compounds I-1 to I-88, respectively. Their specific structures are as follows: .

[0021] The preparation routes for the above-mentioned quinoxaline compounds I-1 to I-88 are as follows: .

[0022] This invention modifies quinoxaline by introducing aromatic rings, heterocyclic aromatic rings, and fused rings at the 2-position, and aniline, phenol, and phenylhydrazine groups at the 3-position. Simultaneously, it introduces different electron-donating and electron-withdrawing groups at the 6- and / or 7-positions, thus designing and synthesizing a novel class of quinoxaline compounds. The compounds prepared by this invention exhibit good inhibitory activity against LSD1 and are suitable for drug development.

[0023] Example 1

[0024] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-1. The preparation method of compound I-1 includes the following steps: reacting compound a1 (2,3-dichloroquinoxaline) (500 mg, 2.51 mmol), N,N -Diisopropylethylamine (0.66 mL, 3.77 mmol) dissolved in N , N Add 5 mL of dimethylformamide, then add N 5-Methylpiperazine (0.56 mL, 5.02 mmol) was reacted with the reaction mixture at 100 °C, and the reaction progress was monitored by TLC. After the reaction was complete, ethyl acetate (25 mL) was added to the resulting reaction system, the organic phase was washed with saturated brine (3 × 25 mL), dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and intermediate a2 was obtained by column chromatography. Intermediate a2 (100 mg, 0.38 mmol), 5-methylthiophene-2-boronic acid (65 mg, 0.46 mmol), potassium carbonate (105 mg, 0.76 mmol), and tetrakis(triphenylphosphine)palladium (22 mg, 0.019 mmol) were dissolved in a mixed solution of tetrahydrofuran and water (V tetrahydrofuran:V water = 3:1, 8 mL), and reacted at 65 °C under nitrogen protection, with the reaction progress monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature, the crude reaction mixture was washed with 3 × 20 mL of water, and the aqueous phase was extracted with 3 × 20 mL of dichloromethane. The extracted organic phase was dried over anhydrous sodium sulfate, followed by filtration to remove the drying agent. The filtered organic phases were combined, the solvent was removed by rotary evaporation, and compound I-1 was obtained by column chromatography in 54.7% yield. The structure of compound I-1 was analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows: 1H NMR (400MHz, CDCl3) δ7.91–7.89 (m, 2H), 7.79 (dd, J = 8.2, 1.7 Hz, 1H), 7.54-7.50 (m, 1H), 7.48-7.44 (m, 1H), 6.76 (d, J = 3.8 Hz, 1H), 3.38 (s, 4H), 2.57 (t, J = 5.0Hz, 4H), 2.52 (s, 3H), 2.34 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 153.85,143.98, 143.14, 140.04, 139.80, 138.87, 129.05, 128.55, 128.31, 127.21,127.06, 126.25, 54.74, 49.47, 46.32, 15.72. HRMS (ESI) calcd for C 18 H 20 N4S [M+H]+, 325.1481; found, 325.1484. HPLC retention time = 4.574 min, purity = 97.89% l =254 nm).

[0025] Example 2

[0026] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-2. The preparation method of compound I-2 is basically the same as in Example 1, except that: [The text abruptly ends here, so the translation stops.] N The -methylpiperazine was replaced with 4-(4-methylpiperazine)aniline. The yield of compound I-2 was 51.1%. The structure of compound I-2 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.88 (dd, J = 8.2, 1.6 Hz, 1H), 7.74 (dd, J =8.3, 1.4 Hz, 1H), 7.69 (d, J = 2.3 Hz, 1H), 7.67 (d, J= 2.2 Hz, 1H), 7.57–7.52 (m, 2H), 7.43–7.42 (m, 1H), 7.41–7.38 (m, 1H), 6.99 (d, J = 2.3 Hz, 1H), 6.97 (d, J = 2.3 Hz, 1H), 6.88 (dd, J = 3.6, 1.2 Hz, 1H), 3.22–3.19 (m, 4H), 2.61–2.59 (m, 4H), 2.59 (s, 3H), 2.36 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ147.72, 144.62, 140.64, 140.44, 137.92, 137.58, 131.94, 129.76, 128.62,127.42, 126.58, 126.45, 125.48, 121.41, 49.88, 46.29, 15.64. HRMS (ESI) calcdfor C 24 H 25 N5S [M+H]+, 416.1909; found, 416.1903. HPLC retention time = 4.749 min, purity = 96.18%, (λ = 254 nm).

[0027] Example 3

[0028] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-3. The preparation method of compound I-3 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with aniline. The yield of compound I-3 was 50.3%. The structure of compound I-3 was analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows: 1 H NMR (400MHz, CDCl3) δ 7.91 (dd, J = 8.3, 1.5 Hz, 1H), 7.83-7.78 (m, 3H), 7.60-7.56(m, 2H), 7.54 (d, J = 3.5 Hz, 1H), 7.47-7.43 (m, 1H), 7.41–7.36 (m, 2H), 7.12-7.08 (m, 1H), 6.89-6.87 (m, 1H), 2.59 (d, J = 1.2 Hz, 3H). 13C NMR (100MHz, CDCl3) δ 146.53, 144.82, 140.68, 140.17, 139.44, 137.80, 137.76, 129.89,129.12, 128.69, 127.57, 126.73, 126.52, 125.95, 123.23, 119.79, 15.63. HRMS(ESI) calcd for C 19 H 15 N3S [M+H]+, 318.1059; found, 318.1056. HPLC retention time = 4.876 min, purity = 95.03%, ( l = 254 nm).

[0029] Example 4

[0030] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-4. The preparation method of compound I-4 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with phenol. The yield of compound I-4 was 76.3%. The structure of compound I-3 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400MHz, CDCl3) δ 8.12 (d, J = 3.8 Hz, 1H), 8.01–7.99 (m, 1H), 7.67–7.65 (m, 1H), 7.58–7.53 (m, 2H), 7.51-7.46 (m, 2H), 7.34–7.28 (m, 3H), 6.86 (dd, J = 3.8,1.1 Hz, 1H), 2.58 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 153.57, 152.75, 145.71,140.96, 139.58, 138.69, 137.98, 131.52, 129.71, 129.16, 128.35, 127.76,127.19, 127.03, 125.52, 122.02, 15.80. HRMS (ESI) calcd for C 19 H 14N₂OS [M+H]⁺, 319.0900; found, 319.0888. HPLC retention time = 5.231 min, purity = 96.77%, ( l = 254nm).

[0031] Example 5

[0032] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-5. The preparation method of compound 5 is basically the same as in Example 1, except that: [The method involves...] N -Methylpiperazine was replaced with phenylhydrazine. The yield of compound I-5 was 50.3%. The structure of compound I-5 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400MHz, CDCl3) δ 8.19–8.15 (m, 3H), 8.10 (dd, J = 8.3, 0.8 Hz, 1H), 7.77-7.73(m, 1H), 7.71–7.67 (m, 2H), 7.63–7.59 (m, 3H), 6.82 (dd, J = 3.7, 1.1 Hz, 1H), 2.55 (d, J = 1.2 Hz, 3H). 13 C NMR (100 MHz, CDCl3) δ 153.34, 153.14,146.68, 145.60, 142.94, 139.81, 138.20, 133.11, 132.45, 130.97, 130.42,129.92, 129.49, 128.76, 127.13, 124.63, 15.80. HRMS (ESI) calcd for C 19 H 16 N4S[M+H]+, 333.1168; found, 333.1171. HPLC retention time = 5.254 min, purity = 95.15%, ( l = 254 nm).

[0033] Example 6

[0034] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-6. The preparation method of compound I-6 is basically the same as in Example 1, except that: [The method involves...] N-Methylpiperazine was replaced with benzylamine. The yield of compound I-6 was 65.2%. The structure of compound I-6 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400MHz, CDCl3) δ 7.88–7.86 (m, 1H), 7.71 (dd, J = 8.4, 1.2 Hz, 1H), 7.55-7.51(m, J = 8.3, 6.9, 1.4 Hz, 1H), 7.45–7.41 (m, 1H), 7.40–7.33 (m, 3H), 7.31–7.27 (m, 3H), 6.79-6.78 (m, 1H), 5.83 (t, J = 5.7 Hz, 1H), 4.81 (d, J = 5.5Hz, 2H), 2.54 (d, J = 0.9 Hz, 3H). 13 C NMR (100 MHz, CDCl3) δ 149.29, 144.24,141.00, 140.12, 138.95, 138.21, 137.20, 129.63, 128.84, 128.71, 128.10,127.56, 127.26, 126.34, 126.11, 124.91, 45.82, 15.57. HRMS (ESI) calcd forC 20 H 17 N3S [M+H]+, 332.1216; found, 332.1207. HPLC retention time = 4.938 min, purity = 97.59%, ( l = 254 nm).

[0035] Example 7

[0036] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-7. The preparation method of compound I-7 is basically the same as in Example 1, except that: [The method involves...] N -Methylpiperazine was replaced with N -Methylbenzylamine. The yield of compound I-7 obtained was 60.2%. The structure of compound I-7 was analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows: 1 HNMR (400 MHz, THF- d8) δ 7.90 (s, 1H), 7.89–7.88 (m, 1H), 7.78 (dd, J = 8.2,1.6 Hz, 1H), 7.59–7.55 (m, 1H), 7.53–7.49 (m, 1H), 7.37 (d, J = 6.9 Hz, 2H), 7.31 (t, J = 7.3 Hz, 2H), 7.24 (t, J = 7.2 Hz, 1H), 6.84 (dd, J = 3.6, 1.1Hz, 1H), 4.63 (s, 2H), 2.81 (s, 3H), 2.56 (s, 3H). 13 C NMR (100 MHz, THF- d 8) δ153.87, 143.88, 142.83, 140.40, 139.69, 138.79, 138.15, 128.76, 128.71,128.66, 128.18, 128.02, 126.99, 126.86, 126.53, 126.06, 56.81, 39.47, 14.53.HRMS (ESI) calcd for C 21 H 19 N3S [M+H]+, 346.1372; found, 346.1368. HPLC retention time = 5.348 min, purity = 96.45%, ( l = 254 nm).

[0037] Example 8

[0038] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-8. The preparation method of compound I-8 is basically the same as in Example 1, except that: [The method involves...] N The methylpiperazine was replaced with 2-amino-3-cyano-5-methylthiophene. The yield of compound I-8 was 58.8%. The structure of compound I-8 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.80 (s, 1H), 7.94 (dd, J= 8.4, 1.6 Hz,1H), 7.89–7.87 (m, 1H), 7.65–7.61 (m, 2H), 7.54–7.50 (m, 1H), 6.97 (d, J =2.5 Hz, 1H), 6.63 (d, J = 1.3 Hz, 1H), 2.60 (s, 3H), 2.43 (s, 3H). 13 C NMR(100 MHz, CDCl3) δ 149.54, 145.77, 142.16, 139.59, 138.98, 138.25, 136.70,131.01, 130.31, 128.90, 127.49, 127.19, 127.10, 126.19, 120.54, 115.57,91.48, 15.67, 14.81. HRMS (ESI) calcd for C 19 H 14 N4S2 [M+H]+, 363.0733; found, 363.0738. HPLC retention time = 5.355 min, purity = 95.10%, ( l = 254 nm).

[0039] Example 9

[0040] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-9. The preparation method of compound I-9 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 1-methyl-5-aminotetrazole. The yield of compound I-9 was 32.4%. The structure of compound I-9 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 13.27 (s, 1H), 8.41 (d, J = 3.5 Hz, 1H), 7.87(d, J = 7.8 Hz, 1H), 7.55 – 7.51 (m, 1H), 7.45 – 7.40 (m, 2H), 6.89 (s, 1H), 4.18 (s, 3H), 2.59 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 157.50, 148.79, 147.70,144.09, 135.89, 134.35, 132.77, 130.02, 129.07, 128.37, 126.18, 125.58,116.06, 32.85, 15.73. HRMS (ESI) calcd for C 15 H 13 N7S[M + H] + , 324.1026; found,324.1027. HPLC retention time = 4.738 min, purity = 97.68%, ( l = 254 nm).

[0041] Example 10

[0042] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-10. The preparation method of compound I-10 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 5-amino-3-methylisoxazole. The yield of compound I-10 was 64.7%. The structure of compound I-10 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.32 (s, 1H), 7.97 (d, J = 7.5 Hz, 1H), 7.87 (d, J = 8.7 Hz, 1H), 7.65 (t, J = 7.3 Hz, 1H), 7.56 (t, J = 7.6 Hz, 1H),7.49 (s, 1H), 6.89 (d, J = 3.6 Hz, 1H), 6.71 (s, 1H), 2.59 (s, 3H), 2.35 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 161.86, 161.00, 145.50, 142.41, 139.88,139.72, 138.43, 136.51, 130.30, 128.94, 127.85, 127.35, 126.91, 126.78,88.56, 15.62, 12.16. HRMS (ESI) calcd for C 17 H14 N4OS[M + H] + , 323.0961; found, 323.0962. HPLC retention time = 4.582 min, purity = 97.06%, ( l = 254 nm).

[0043] Example 11

[0044] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-11. The preparation method of compound I-11 includes the following steps: 2,3-dichloroquinoxaline (compound a1) (500 mg, 2.51 mmol), phenylboronic acid (368 mg, 3.01 mmol), potassium carbonate (694 mg, 5.02 mmol), and tetra(triphenylphosphine)palladium (145 mg, 0.1255 mmol) are dissolved in a mixed solution of tetrahydrofuran and water (Vtetrahydrofuran:Vwater = 3:1, 20 mL). The reaction is carried out under nitrogen protection at 65 °C, and the reaction progress is monitored by thin-layer chromatography. After the reaction is complete, the mixture is cooled to room temperature, the crude reaction mixture is washed with 3 × 40 mL of water, and the aqueous phase is extracted with 3 × 30 mL of dichloromethane. The extracted organic phase is dried over anhydrous sodium sulfate, and then filtered to remove the drying agent. The filtered organic phases are combined, the solvent is removed by rotary evaporation, and the intermediate a62 is obtained by column chromatography. Intermediate a62 (100 mg, 0.42 mmol), 5-methylthiophene-2-boronic acid (71 mg, 0.50 mmol), potassium carbonate (115 mg, 0.83 mmol), and tetra(triphenylphosphine)palladium (24 mg, 0.020 mmol) were dissolved in a mixed solution of tetrahydrofuran and water (Vtetrahydrofuran:Vwater = 3:1, 8 mL). The reaction was carried out under nitrogen protection at 65 °C, and the reaction progress was monitored by thin-layer chromatography. After the reaction was completed, the mixture was cooled to room temperature, the crude reaction mixture was washed with 3 × 20 mL of water, and the aqueous phase was extracted with 3 × 20 mL of dichloromethane. The extracted organic phase was dried over anhydrous sodium sulfate and then filtered to remove the drying agent. The filtered organic phases were combined, the solvent was removed by rotary evaporation, and compound II-11 was obtained by column chromatography in 47.8% yield. The structure of compound II-11 was analyzed by nuclear magnetic resonance, and the structural characterization results were as follows: 1 H NMR (400 MHz, CDCl3) δ 8.09 – 8.08 (m, 1H), 8.07 – 8.06 (m, 1H), 7.75 – 7.66 (m, 2H), 7.62 (d, J = 2.3 Hz, 1H), 7.61 (d, J= 4.3 Hz,1H), 7.50 (s, 1H), 7.49 (s, 1H), 7.48 (d, J = 1.4 Hz, 1H), 6.53-6.51 (m, 2H), 2.48 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 152.47, 147.12, 144.65, 141.26,140.43, 140.28, 139.69, 130.44, 130.20, 129.49, 129.27, 129.16, 129.10,128.82, 128.79, 126.42, 15.63. HRMS (ESI) calcd for C 19 H 14 N2S[M + H] + ,303.0950; found, 303.0944. HPLC retention time = 4.845 min, purity = 99.29%, ( l = 254nm).

[0045] Example 12

[0046] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-12. The preparation method of compound I-12 is basically the same as in Example 1, except that: [The text abruptly ends here, so the translation stops.] N The -methylpiperazine was replaced with 4-(2-pyridyl)aniline. The yield of compound I-12 was 57.0%. The structure of compound I-12 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J = 4.8 Hz, 1H), 8.07 (s, 1H), 8.05(s, 1H), 7.96 (s, 1H), 7.94 (s, 1H), 7.92 (s, 1H), 7.83 (d, J = 8.3 Hz, 1H), 7.74 (d, J = 3.3 Hz, 1H), 7.71 (s, 1H), 7.61 (t, J = 8.5 Hz, 1H), 7.56 (d, J = 3.5 Hz, 1H), 7.47 (t, J = 6.9 Hz, 1H), 7.20 (q,J = 4.5 Hz, 1H), 6.91 (d, J = 2.5 Hz, 1H), 2.61 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 157.03, 149.70,146.32, 144.93, 140.74, 140.32, 140.13, 137.85, 137.66, 136.87, 134.01,129.98, 128.73, 127.67, 126.79, 126.59, 126.16, 121.77, 120.09, 119.70,15.64. HRMS (ESI) calcd for C 24 H 18 N4S[M + H] + , 395.1325; found, 395.1329. HPLC retention time = 4.948 min, purity = 95.70%, ( l = 254 nm).

[0047] Example 13

[0048] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-13. The preparation method of compound I-13 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 4-(1H-pyrazol-1-yl)aniline. The yield of compound I-13 was 73.5%. The structure of compound I-13 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.92 (d, J = 8.9 Hz, 3H), 7.80 (d, J =8.3 Hz, 1H), 7.72 (s, 1H), 7.71 (s, 1H), 7.69 (s, 1H), 7.65 (s, 1H), 7.60 (t, J = 6.9 Hz, 1H), 7.55 (d, J = 3.6 Hz, 1H), 7.47 (t, J = 6.8 Hz, 1H), 6.90 (d, J = 4.8 Hz, 1H), 6.47 (s, 1H), 2.60 (s, 3H). 13C NMR (100 MHz, CDCl3) δ146.34, 144.94, 140.94, 140.64, 140.04, 137.93, 137.84, 137.59, 135.66,130.00, 128.73, 127.64, 126.78, 126.69, 126.57, 126.14, 120.54, 120.05,107.52, 15.64. HRMS (ESI) calcd for C 22 H 17 N5S [M + H] + , 384.1277; found, 384.1266. HPLC retention time = 4.723 min, purity = 96.68%, ( l = 254 nm).

[0049] Example 14

[0050] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-14. The preparation method of compound I-14 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 4-(1H-pyrrolidine)aniline. The yield of compound I-14 was 71.4%. The structure of compound I-14 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.92 (d, J = 7.2 Hz, 1H), 7.88 (s, 1H), 7.86(s, 1H), 7.80 (d, J = 8.2 Hz, 1H), 7.60 – 7.57 (m, 2H), 7.55 (d, J = 3.6 Hz, 1H), 7.46 (t, J = 7.2 Hz, 1H), 7.42 (s, 1H), 7.40 (s, 1H), 7.08 (s, 2H), 6.90(d, J = 4.6 Hz, 1H), 6.36 (s, 1H), 2.60 (s, 3H). 13C NMR (100 MHz, CDCl3) δ146.39, 144.93, 140.63, 140.08, 137.85, 137.66, 137.20, 136.26, 130.00,128.73, 127.61, 126.67, 126.55, 126.10, 121.36, 120.80, 119.56, 110.26,15.64. HRMS (ESI) calcd for C 23 H 18 N4S [M + H] + , 383.1325; found, 383.1322. HPLC retention time = 5.080 min, purity = 96.07%, ( l = 254 nm).

[0051] Example 15

[0052] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-15. The preparation method of compound I-15 is basically the same as in Example 1, except that: [The method involves...] N -Methylpiperazine was replaced with p-aminoanisole. The yield of compound I-15 was 82.2%. The structure of compound I-15 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.88 (dd, J = 8.2, 1.6 Hz, 1H), 7.73 (dd, J =8.3, 1.5 Hz, 1H), 7.70-7.68 (m, 1H), 7.67-7.66 (m, 1H), 7.57 – 7.53 (m, 1H),7.52 (d, J = 3.4 Hz, 1H), 7.45 – 7.41 (m, 1H), 7.41 – 7.36 (m, 1H), 6.94-6.93(m, 1H), 6.92-6.90 (m, 1H), 6.84 (dd, J = 3.6, 1.1 Hz, 1H), 3.81 (s, 3H), 2.57 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 155.89, 146.91, 144.63, 140.59,140.37, 137.92, 137.64, 132.53, 129.78, 128.64, 127.47, 126.58, 126.45,125.56, 121.92, 114.31, 55.66, 15.62. HRMS (ESI) calcd for C 20 H 17 N3OS[M + H] + ,348.1165; found, 348.1160. HPLC retention time = 4.921 min, purity = 96.88%, ( l = 254nm).

[0053] Example 16

[0054] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-16. The preparation method of compound I-16 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 4-aminoanisidine thioether. The yield of compound I-16 was 81.4%. The structure of compound I-16 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.90 (dd, J = 8.3, 1.5 Hz, 1H), 7.78 – 7.76 (m,2H), 7.74-7.73 (m, 1H), 7.59 – 7.57 (m, 1H), 7.55 – 7.54 (m, 1H), 7.51 (d, J = 3.5 Hz, 1H), 7.46-7.42 (m, 1H), 7.34-7.32 (m, 1H), 7.31-7.30 (m, 1H), 6.87(dd, J = 3.7, 1.1 Hz, 1H), 2.59 (s, 3H), 2.49 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 146.41, 144.85, 140.63, 140.12, 137.74, 137.68, 137.26, 132.03,129.93, 128.69, 127.61, 127.56, 126.65, 126.53, 125.99, 120.45, 17.30, 15.65.HRMS (ESI) calcd for C 20 H 17 N3S2[M + H] + , 364.0937; found, 364.0934. HPLC retention time = 5.055 min, purity = 95.14%, ( l = 254 nm).

[0055] Example 17

[0056] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-17. The preparation method of compound I-17 is basically the same as in Example 1, except that: [The method involves...] N -Methylpiperazine was replaced with N,N -Diethyl-p-phenylenediamine. The yield of compound I-17 obtained was 50.0%. The structure of compound I-17 was analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.85 (d, J = 8.3 Hz, 1H), 7.70 (d, J = 8.4Hz, 1H), 7.58 (s, 1H), 7.56 (s, 1H), 7.51 – 7.47 (m, 2H), 7.36 – 7.33 (m,1H), 6.79 (d, J = 3.8 Hz, 1H), 6.71 (s, 1H), 6.69 (s, 1H), 3.32 (q, J = 7.1Hz, 4H), 2.53 (s, 3H), 1.14 (t, J = 7.0 Hz, 6H). 13C NMR (100 MHz, CDCl3) δ147.24, 144.78, 144.44, 140.73, 140.70, 138.15, 137.49, 129.65, 128.59,128.11, 127.34, 126.53, 126.41, 125.12, 122.43, 112.81, 44.82, 15.65, 12.73.HRMS (ESI) calcd for C 23 H 24 N4S [M + H] + , 389.1794; found, 389.1792. HPLC retention time = 4.907 min, purity = 96.23%, ( l = 254 nm).

[0057] Example 18

[0058] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-18. The preparation method of compound I-18 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with aniline. The yield of compound I-18 was 81.5%. The structure of compound I-18 was analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.87 (dd, J = 8.3, 1.2 Hz, 1H), 7.72 (dd, J = 8.3, 1.3 Hz,1H), 7.56 – 7.51 (m, 4H), 7.41 – 7.37 (m, 2H), 6.86 (dd, J = 3.6, 1.1 Hz,1H), 6.74-6.72 (m, 1H), 6.71-6.70 (m, 1H), 2.58 (d, J = 1.1 Hz, 3H). 13C NMR(100 MHz, CDCl3) δ 147.16, 144.53, 142.72, 140.63, 140.53, 137.96, 137.52,130.76, 129.72, 128.60, 127.42, 126.51, 126.41, 125.34, 122.29, 115.71,15.61. HRMS (ESI) calcd for C 19 H 16 N4S[M + H] + , 333.1168; found, 333.1169. HPLC retention time = 4.211 min, purity = 96.59%, ( l = 254 nm).

[0059] Example 19

[0060] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-19. The preparation method of compound I-19 is basically the same as in Example 1, except that: [The method involves...] N -Methylpiperazine was replaced with N -Methyl-p-phenylenediamine. The yield of compound I-19 was 54.2%. The structure of compound I-19 was analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.86 (d, J = 8.3 Hz, 1H), 7.71 (d, J = 8.4 Hz,1H), 7.57 – 7.50 (m, 4H), 7.40 – 7.36 (m, 2H), 6.86 (d, J = 3.7 Hz, 1H), 6.66(d, J = 8.9 Hz, 2H), 2.85 (s, 3H), 2.58 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ147.27, 145.94, 144.49, 140.65, 138.01, 137.49, 129.69, 128.59, 127.39,126.50, 126.40, 125.23, 122.50, 113.01, 31.35, 15.61. HRMS (ESI) calcd forC 20 H 18N4S[M + H] + , 347.1325; found, 347.1320. HPLC retention time = 4.471 min, purity = 98.91%, ( l = 254 nm).

[0061] Example 20

[0062] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-20. The preparation method of compound I-20 is basically the same as in Example 1, except that: [The method involves...] N -Methylpiperazine was replaced with N -Boc-p-phenylenediamine. The yield of compound I-20 obtained was 81.4%. The structure of compound I-20 was analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 8.3 Hz, 1H), 7.73 (t, J = 9.4 Hz,3H), 7.57 – 7.55 (m, 1H), 7.53 – 7.50 (m, 2H), 7.44 – 7.42 (m, 1H), 7.40-7.36(t, J = 7.6 Hz, 2H), 6.87 (d, J = 4.7 Hz, 1H), 6.50 (s, 1H), 2.58 (s, 3H), 1.52 (s, 9H). 13 C NMR (100 MHz, CDCl3) δ 153.01, 146.67, 144.72, 140.61,140.26, 137.75, 137.67, 134.74, 133.89, 129.85, 128.64, 127.52, 126.60,126.50, 125.74, 120.80, 119.40, 80.54, 15.61. HRMS (ESI) calcd for C 24 H 24 N4O2S[M + H] + , 433.1693; found, 433.1691. HPLC retention time = 4.640 min, purity = 98.67%, ( l = 254 nm).

[0063] Example 21

[0064] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-21. The preparation method of compound I-21 is basically the same as that in Example 1, except that: N The -methylpiperazine was replaced with 4-methanesulfonamide aniline. The yield of compound I-21 was 75.9%. The structure of compound I-21 was analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows: 1 H NMR (400 MHz, DMSO- d 6) δ 9.56 (s, 1H), 8.84 (s, 1H), 7.82 – 7.78 (m,4H), 7.66 (d, J = 8.2 Hz, 1H), 7.59 (t, J = 7.3 Hz, 1H), 7.48 (t, J =7.8 Hz,1H), 7.23 (s, 1H), 7.21 (s, 1H),6.97 (d, J = 4.3 Hz, 1H), 2.97 (s, 3H), 2.56 (s, 3H). 13 C NMR (100 MHz, DMSO- d 6) δ 147.07, 144.74, 141.37, 139.64, 138.34,137.60, 137.42, 133.24, 130.21, 129.58, 128.29, 127.56, 126.53, 122.18,122.15, 15.69. HRMS (ESI) calcd for C 20 H 18 N4O2S2[M+H] + , 411.0944; found, 411.0963. HPLC retention time = 4.242 min, purity = 98.54%, ( l =254nm).

[0065] Example 22

[0066] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-22. The preparation method of compound I-22 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 4-aminoacetanilide. The yield of compound I-22 was 48.6%. The structure of compound I-22 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows:1 H NMR (400 MHz, DMSO- d 6) δ 9.91 (s, 1H), 8.74 (s, 1H), 7.80 (s, 1H), 7.79(s, 11H), 7.73 (s, 1H), 7.71 (s, 11H), 7.65–7.55 (m, 4H), 7.46 (t, J = 7.5Hz, 1H), 6.97 (s, 1H), 2.56 (s, 3H), 2.05 (s, 3H). 13 C NMR (100 MHz, DMSO- d 6)δ 168.47, 147.25, 144.59, 141.28, 139.82, 138.55, 137.53, 135.84, 135.01,130.07, 129.50, 128.30, 127.51, 126.53, 126.23, 121.93, 119.78, 24.46, 15.73.HRMS (ESI) calcd for C 21 H 18 N4OS [M + H] + , 375.1274; found, 375.1260. HPLC retention time = 4.371 min, purity = 98.55%, ( l = 254nm).

[0067] Example 23

[0068] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-23. The preparation method of compound I-23 includes the following steps: compound II-25 (100 mg, 0.20 mmol) is dissolved in dichloromethane solution (5 mL), followed by the addition of trifluoroacetic acid (0.03 mL, 0.40 mmol). The reaction is carried out at room temperature, and the reaction progress is monitored by thin-layer chromatography. After the reaction is complete, the solvent is removed by rotary evaporation, followed by the addition of water (5 mL) and washing of the reaction mixture with saturated sodium bicarbonate aqueous solution until pH 7. The crude reaction mixture is washed with 3 × 40 mL of water and the aqueous phase is extracted with 3 × 30 mL of dichloromethane. The extracted organic phase is dried over anhydrous sodium sulfate and then filtered to remove the drying agent. The filtered organic phases are combined, the solvent is removed by rotary evaporation, and compound I-23 is obtained by column chromatography with a yield of 87.5%. The structure of compound I-23 is analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows: 1H NMR (400 MHz, CDCl3) δ 7.88(d, J = 6.5 Hz, 1H), 7.74 (d, J = 8.3 Hz, 1H),7.69 (s, 1H),7.67(s,1H), 7.57–7.54 (m,1H), 7.53(s, 1H), 7.44 – 7.43 (m, 1H),7.41 – 7.39 (m, 1H), 6.99 (s, 1H), 6.96 (s, 1H), 6.88 (d, J = 4.8 Hz, 1H), 3.14-3.11 (m, 1H), 3.07-3.04 (m, 1H), 2.59 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ148.27, 146.89, 144.61, 140.64, 140.45, 137.92, 137.59, 132.01, 129.76,128.63, 127.43, 126.57, 126.44, 125.48, 121.41, 117.09, 51.19, 46.26, 15.62.HRMS (ESI) calcd for C 23 H 23 N5S[M + H] + , 402.1747; found, 402.1748. HPLC retention time = 3.374 min, purity = 95.65%, ( l =254nm).

[0069] Example 24

[0070] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-24. The preparation method of compound I-24 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 4-(4-ethylpiperazin-1-yl)aniline. The yield of compound I-24 was 68.9%. The structure of compound I-24 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.88 (dd, J = 8.3, 1.6 Hz, 1H), 7.74(dd, J= 8.3, 1.4 Hz, 1H), 7.69 (s, 1H), 7.67 (s, 1H), 7.56 – 7.53 (m, 2H), 7.43-7.42 (m, 1H), 7.41 – 7.38 (m, 1H), 6.99 (s, 1H), 6.97 (s, 1H), 6.87 (dd, J = 3.6, 1.1 Hz, 1H), 3.23 – 3.20 (m, 4H), 2.65 – 2.63 (m, 4H), 2.59 (s, 3H), 2.49 (q, J = 7.2 Hz, 2H), 1.14 (t, J = 7.2 Hz, 3H). 13 C NMR (100 MHz, CDCl3) δ147.79, 146.88, 144.59, 140.64, 140.45, 137.94, 137.59, 131.93, 129.75,128.62, 127.42, 126.58, 126.43, 125.46, 121.41, 116.97, 52.96, 52.48, 49.89,15.62, 12.11. HRMS (ESI) calcd for C 25 H 27 N5S[M + H] + , 430.2060; found,430.2057. HPLC retention time = 4.397 min, purity = 95.71%, ( l = 254nm).

[0071] Example 25

[0072] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-25. The preparation method of compound I-25 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 1-Boc-4-(4-aminophenyl)piperazine. The yield of compound I-25 was 72.8%. The structure of compound I-25 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 6.5 Hz, 1H), 7.74 (d, J= 8.4 Hz, 1H), 7.71 (s, 1H), 7.68 (s, 1H), 7.56 (d, J = 8.4 Hz, 1H), 7.53 (d, J = 3.4 Hz, 1H), 7.44 (d, J = 5.3 Hz, 1H), 7.41 (d, J = 6.8 Hz, 1H), 6.98 (s,1H), 6.96 (s, 1H), 6.87 (d, J = 3.6 Hz, 1H), 3.61-3.59 (m, 4H), 3.12-3.09 (m,4H), 2.59 (s, 3H), 1.49 (s, 9H). 13 C NMR (100 MHz, CDCl3) δ 154.84, 147.65,146.81, 144.65, 140.63, 140.38, 137.89, 137.63, 132.52, 129.79, 128.65,127.45, 126.57, 126.45, 125.56, 121.38, 117.65, 80.00, 50.23, 28.55, 15.62.HRMS (ESI) calcd for C 28 H 31 N5O2S[M + H] + , 502.2271; found, 502.2270. HPLC retention time = 5.129 min, purity = 96.41%, ( l = 254 nm).

[0073] Example 26

[0074] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-26. The preparation method of compound I-26 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 4-(4-morpholino)aniline. The yield of compound I-26 was 50.9%. The structure of compound I-26 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400MHz, CDCl3) δ 7.88 (d, J = 6.7 Hz, 1H), 7.74 (d, J =8.3Hz, 1H), 7.69 (d,J = 9.0 Hz, 1H), 7.55 (d, J = 6.9 Hz, 1H), 7.53 (d, J = 3.6 Hz, 1H), 7.44 (d, J = 5.5 Hz, 1H), 7.40 (d, J = 6.9 Hz, 1H), 6.96 (s, 1H), 6.94 (s,1H), 6.86 (d, J = 3.6 Hz, 1H), 3.89 – 3.86 (m,4H), 3.15–3.13 (m, 4H), 2.58 (s,3H). 13 C NMR (100 MHz, CDCl3)δ 147.67,146.85,144.63, 140.63, 140.41, 137.92,137.62, 132.26, 129.78, 128.64, 127.45, 126.57, 126.45, 125.53, 121.47,116.65, 67.06, 50.12, 15.63. HRMS (ESI) calcd for C 23 H 22 N4OS [M + H] + ,403.1587; found, 403.1581. HPLC retention time = 4.807 min, purity = 95.61%, ( l = 254nm).

[0075] Example 27

[0076] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-27. The preparation method of compound I-27 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 4-(4-aminophenyl)morpholin-3-one. The yield of compound I-27 was 69.6%. The structure of compound I-27 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.92 (d, J = 8.2 Hz, 1H), 7.87 (s,1H), 7.85 (s, 1H), 7.78 (d, J= 6.8 Hz, 11H), 7.61 (s, 1H), 7.58 (d, J = 6.9Hz, 1H), 7.53 (d, J = 3.6 Hz, 1H), 7.48 – 7.45 (m, 1H), 7.35 (s, 1H), 7.33(s, 1H), 6.90 (d, J = 4.6 Hz, 1H), 4.36 (s, 3H), 4.05 (t, J = 5.1 Hz, 2H), 3.78 (t, J = 5.1 Hz, 2H), 2.61 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 166.90,146.24, 144.94, 140.66, 139.99, 138.33, 137.91, 137.65, 136.15, 129.95,128.71, 127.66, 126.67, 126.58, 126.25, 126.16, 120.39, 68.71, 64.29, 49.95,15.64. HRMS (ESI) calcd for C 23 H 20 N4O2S[M + H] + , 417.1380; found, 417.1376.HPLC retention time = 4.355 min, purity = 95.26%, ( l = 254nm).

[0077] Example 28

[0078] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-28. The preparation method of compound I-28 is basically the same as in Example 23, except that compound I-29 is replaced by compound I-25. The yield of compound I-28 obtained is 73.1%. The structure of compound I-28 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.90 (d, J =7.4 Hz, 1H), 7.79 – 7.73 (m, 3H), 7.57(t, J = 7.6 Hz, 1H), 7.53 (s, 2H), 7.44 (t, J= 7.4 Hz, 1H), 7.24 (s, 1H), 6.88 (s, 1H), 4.13 (s, 4H), 3.44 (d, J =10.9Hz,2H), 2.92 (s, 2H), 2.71 (s,1H), 2.59 (s, 3H). 13 C NMR (100 MHz, CDCl3)δ144.81,140.65,140.17,137.88,137.76, 129.88, 128.67, 127.54, 127.36, 126.67,126.51, 125.91, 120.12, 45.78,41.21, 32.07, 15.62. HRMS (ESI) calcd for C 24 H 24 N4S[M+H] + , 401.1794; found, 401.1799. HPLC retention time = 3.499 min, purity = 95.47%, ( l =254nm).

[0079] Example 29

[0080] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-29. The preparation method of compound I-29 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 1-Boc-4-(4-aminophenyl)piperidine. The yield of compound I-29 was 77.6%. The structure of compound I-29 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.91 (d, J = 8.2 Hz, 1H), 7.78 (d, J = 8.3 Hz, 1H), 7.75 (s, 1H), 7.73 (s, 1H), 7.60 – 7.56 (m, 1H), 7.53 (d, J =3.5 Hz, 2H), 7.46 – 7.42 (m, 1H), 7.24 (s, 1H), 7.21 (s, 1H), 6.89 (dd, J =3.6, 1.1 Hz, 1H), 4.26 (s, 2H), 2.82 (s, 2H), 2.67 (d, J= 12.0 Hz, 1H), 2.60(s, 3H), 1.84 (d, J = 12.3 Hz, 2H), 1.63 (s, 2H), 1.49 (s, 9H). 13 C NMR (100MHz, CDCl3) δ 155.00, 146.55, 144.78, 140.84, 140.67, 140.22, 137.80, 137.58,129.87, 128.68, 127.53, 127.38, 126.67, 126.50, 125.86, 120.05, 79.55, 42.28,33.40, 28.60, 15.62. HRMS (ESI) calcd for C 29 H 32 N4O2S[M + H] + , 501.2319; found,501.2322. HPLC retention time = 5.501 min, purity = 98.24%, ( l = 254 nm).

[0081] Example 30

[0082] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-30. The preparation method of compound I-30 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 4-piperidineaniline. The yield of compound I-30 was 38.5%. The structure of compound I-30 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 9.8 Hz, 1H), 7.74 (d, J = 8.4 Hz, 1H),7.67 (s, 1H), 7.65 (s, 1H), 7.56 – 7.53 (m, 2H), 7.43 – 7.42 (m, 1H), 7.40 –7.38 (m, 1H), 6.99 (s, 1H), 6.97 (s, 1H), 6.87 (d, J = 3.6 Hz, 1H), 3.14 –3.12 (m, 4H), 2.59 (s, 3H), 1.76-1.70 (m, 4H), 1.60-1.54 (m, 2H). 13C NMR (100MHz, CDCl3) δ 148.85, 146.94, 144.56, 140.67, 140.51, 137.96, 137.56, 131.51,129.73, 128.62, 127.43, 126.57, 126.43, 125.39, 121.36, 117.49, 51.49, 26.03,24.35, 15.63. HRMS (ESI) calcd for C 24 H 24 N4S[M + H] + , 401.1794; found, 401.1793. HPLC retention time = 5.401 min, purity = 97.14%, ( l = 254 nm).

[0083] Example 31

[0084] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-31. The preparation method of compound I-31 is basically the same as that in Example 1, except that: N The -methylpiperazine was replaced with 4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline. The yield of compound I-31 was 53.3%. The structure of compound I-31 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 8.3 Hz, 1H), 7.74 (d, J = 8.3Hz, 1H), 7.68 (s, 1H), 7.65 (s, 1H), 7.57 – 7.53 (m, 2H), 7.43(s, 1H), 7.40 (d, J = 8.0 Hz, 1H), 6.99 (s, 1H), 6.97 (s, 1H), 6.88 (d, J = 3.8Hz, 1H), 3.71 (d, J = 12.4 Hz, 2H), 2.74 – 2.69 (m, 5H), 2.60 (s,6H), 2.44 (s,2H), 2.37 (s, 3H), 1.96 (d, J = 11.8 Hz, 2H), 1.76 – 1.68 (m, 2H). 13C NMR (100MHz, CDCl3) δ 147.78, 146.89, 144.60, 140.65, 140.45, 137.91, 137.57,131.78, 129.75, 128.63, 127.42, 126.55, 126.44, 125.46, 121.38, 117.44,61.89, 55.16, 50.08, 48.64, 45.74, 28.15, 15.62. HRMS (ESI) calcd for C 29 H 34 N6S[M + H] + , 499.2638; found, 499.2636. HPLC retention time = 4.549 min, purity = 95.92%, ( l = 254 nm).

[0085] Example 32

[0086] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-32. The preparation method of compound I-32 is basically the same as in Example 1, except that: [The method involves...] N The methylpiperazine was replaced with 4-(4-aminophenyl)thiomorpholine-1,1-dioxide. The yield of compound I-32 was 72.4%. The structure of compound I-32 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.90 (d, J = 8.2 Hz, 1H), 7.74 (d, J = 9.7 Hz, 2H), 7.70 (s, 1H), 7.57 (t, J = 7.5 Hz, 1H), 7.53 (d, J =3.6 Hz, 1H), 7.46 (s, 1H), 7.43 (d, J =6.9 Hz, 1H), 6.96 (s, 1H), 6.93 (s,1H), 6.87 (d, J = 3.8 Hz, 1H), 3.79 (s, 4H), 3.13 (s, 4H), 2.59 (s, 3H). 13C NMR(100MHz, CDCl3) δ 146.64, 144.79, 144.06, 140.61, 140.20, 137.78, 137.73,133.18, 129.90, 128.70, 127.53, 126.52, 126.49, 125.80, 121.73, 117.69,50.78, 48.56, 15.63. HRMS (ESI) calcd for C 23 H 22 N4O2S2[M + H] + , 451.1257;found, 451.1256. HPLC retention time = 4.228 min, purity = 97.40%, ( l = 254 nm).

[0087] Example 33

[0088] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-33. The preparation method of compound I-33 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 4-(1-pyrrolidinyl)aniline. The yield of compound I-33 was 67.2%. The structure of compound I-33 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.86 (dd, J = 8.3, 1.6 Hz, 1H), 7.70 (dd, J =8.4, 1.5 Hz, 1H), 7.60 (s, 1H), 7.58 (s, 1H), 7.55 – 7.53 (m, 1H), 7.52 –7.49 (m, 1H), 7.39 – 7.36 (m, 1H), 7.35 (s, 1H), 6.86 (d, J = 2.5 Hz, 1H), 6.61 (s, 1H), 6.59 (s, 1H), 3.31 – 3.28 (m, 4H), 2.58 (s, 3H), 2.03 – 1.99 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 147.40, 145.17, 144.39, 140.78, 140.67,138.15, 137.46, 129.59, 128.57, 127.90, 127.30, 126.53, 126.40, 125.02,122.64, 111.93, 48.02, 25.57, 15.59. HRMS (ESI) calcd for C 23 H 22 N4S[M + H] + ,387.1638; found, 387.1630. HPLC retention time = 5.462 min, purity = 98.61%, ( l = 254nm).

[0089] Example 34

[0090] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-34. The preparation method of compound I-34 is basically the same as in Example 1, except that: [The text abruptly ends here, so the translation stops.] N The -methylpiperazine was replaced with 4-cyclohexaneaniline. The yield of compound I-34 was 49.0%. The structure of compound I-34 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.89 (d, J = 6.9 Hz, 1H), 7.77 (d, J = 7.3 Hz, 1H),7.71 (s, 1H), 7.69 (s, 1H), 7.58 – 7.52 (m, 2H), 7.50 (s, 1H), 7.42 (t, J =7.7 Hz, 1H), 7.24 (d, J = 3.4 Hz, 1H), 7.21 (s, 1H), 6.86 (d, J = 3.9 Hz,1H), 2.58 (s, 3H), 2.50 (s, 1H), 1.91 – 1.84 (m, 4H), 1.75 (d, J = 12.5 Hz,1H), 1.48 – 1.35 (m, 4H), 1.26 (d, J = 7.2 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ146.66, 144.69, 143.30, 140.68, 140.32, 137.91, 137.70, 137.04, 129.80,128.65, 127.49, 127.39, 126.68, 126.47, 125.72, 119.96, 44.15, 34.71, 27.04,26.29, 15.62. HRMS (ESI) calcd for C 25 H 25 N3S[M + H] + , 400.1842; found, 400.1852. HPLC retention time = 6.416 min, purity = 98.41%, ( l = 254nm).

[0091] Example 35

[0092] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-35. The preparation method of compound I-35 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 4-(4-morpholino)aniline. The yield of compound I-35 was 67.8%. The structure of compound I-35 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.51 (d, J = 2.8 Hz, 1H), 8.02 (dd, J = 9.0, 2.9 Hz, 1H), 7.88 (d, J = 8.3 Hz, 1H), 7.69 (d, J = 8.4 Hz, 1H), 7.55 – 7.52(m, 2H), 7.41 (t, J = 7.6 Hz, 1H), 7.30 (s, 1H), 6.85 (d, J = 4.0 Hz, 1H), 6.69 (d, J = 9.0 Hz, 1H), 3.84 – 3.82 (m, 4H), 3.48 – 3.45 (m, 4H), 2.57 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 156.55, 146.93, 144.75, 140.69, 140.40,140.23, 137.77, 131.49, 129.88, 128.66, 127.63, 127.50, 126.50, 125.74,107.04, 66.87, 46.31, 15.63. HRMS (ESI) calcd for C 22 H 21 N5OS[M + H] + , 404.1540;found, 404.1534. HPLC retention time = 4.573 min, purity = 98.97%, ( l = 254 nm).

[0093] Example 36

[0094] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-36. The preparation method of compound I-36 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 3-methyl-4-morpholinoaniline. The yield of compound I-36 was 75.1%. The structure of compound I-36 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.86 (d, J = 8.2 Hz, 1H), 7.73 (d, J =9.8 Hz, 1H), 7.67 (dd, J = 8.7, 2.8 Hz, 1H), 7.52 (t, J = 7.7 Hz, 1H), 7.48 (d, J = 3.6 Hz, 1H), 7.43 (d, J = 2.8 Hz, 1H), 7.40 (s, 1H), 7.37 (d, J = 8.3Hz, 1H), 6.99 (d, J = 8.7 Hz, 1H), 6.77 (d, J = 4.6 Hz, 1H), 3.88 – 3.81 (m,4H), 2.87 – 2.84 (m, 4H), 2.52 (s, 3H), 2.30 (s, 3H). 13C NMR (100 MHz, CDCl3)δ 147.10, 146.67, 144.60, 140.68, 140.30, 137.99, 137.69, 134.90, 133.55,129.76, 128.62, 127.53, 126.61, 126.45, 125.65, 122.90, 119.64, 118.48,67.60, 52.63, 18.08, 15.62. HRMS (ESI) calcd for C 24 H 24 N4OS[M + H] + , 417.1744;found, 417.1740. HPLC retention time = 5.135 min, purity = 96.85%, ( l = 254 nm).

[0095] Example 37

[0096] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-37. The preparation method of compound I-37 is basically the same as in Example 1, except that: [The method involves...] N The methylpiperazine was replaced with 3-fluoro-4-(4-morpholino)-aniline. The yield of compound I-37 was 71.0%. The structure of compound I-37 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.89 (dd, J =8.3, 1.3 Hz, 1H), 7.85 (dd, J = 14.5, 2.4 Hz, 1H), 7.79 (dd, J = 8.4, 1.2 Hz, 1H), 7.60-7.56 (m, 1.5 Hz, 1H), 7.50 (d, J = 3.5 Hz, 1H), 7.46-7.42(m,1H), 7.31-7.28(m,1H), 6.94 (t, J =9.1 Hz,1H), 6.88-6.86(m, 1H), 3.89–3.87 (m,4H), 3.08 – 3.05 (m, 4H), 2.58 (d, J = 1.2 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 156.93, 154.49, 146.32, 144.87,140.54, 140.07, 137.77, 137.59, 135.59, 135.50, 134.87, 134.76,129.98,128.70, 127.54, 126.67, 126.52, 126.03, 119.05, 119.01, 115.54, 115.51,108.95, 108.69, 67.16,51.37,15.62. HRMS (ESI) calcd for C 23 H 21 FN4OS[M + H] + ,421.1493; found, 421.1488. HPLC retention time = 4.889 min, purity = 96.97%, ( l = 254nm).

[0097] Example 38

[0098] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-38. The preparation method of compound I-38 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 3-chloro-4-morpholinoaniline. The yield of compound I-38 was 43.1%. The structure of compound I-38 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 7.93 – 7.90 (m, 2H), 7.79 (d, J = 8.5 Hz, 1H), 7.68 (dd, J = 8.7, 2.7 Hz, 1H), 7.59 (t, J = 7.7 Hz, 1H), 7.51 (d, J = 3.4Hz, 1H), 7.48 (s, 1H), 7.45 (d, J = 7.3 Hz, 1H), 7.10 (d, J = 9.0 Hz, 1H), 6.89 (d, J = 3.6 Hz, 1H), 3.90 (t, J = 4.6 Hz, 4H), 3.07 (t, J= 4.6 Hz (4H), 2.60 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 146.27, 144.92, 140.52, 140.00,137.85, 137.54, 135.66, 129.99, 129.18, 128.72, 127.59, 126.69, 126.53,126.12, 122.19, 120.74, 119.14, 67.23, 52.05, 15.60. HRMS (ESI) calcd forC 23 H 21 ClN4OS [M + H] + , 437.1197; found, 437.1195. HPLC retention time = 5.168 min, purity = 96.53%, ( l = 254 nm).

[0099] Example 39

[0100] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-39. The preparation method of compound I-39 is basically the same as in Example 1, except that: [The method involves...] N The -methylpiperazine was replaced with 2-methoxy-4-morpholinoaniline. The yield of compound I-39 was 85.6%. The structure of compound I-39 was analyzed by nuclear magnetic resonance, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 8.8 Hz, 1H), 8.31 (s, 1H), 7.88 (dd, J = 8.3, 1.6 Hz, 1H), 7.78 (dd, J = 8.3, 1.4 Hz, 1H), 7.66 (d, J =3.6 Hz, 1H), 7.57-7.53 (m, 1H), 7.42-7.38 (m, 1H), 6.89 (dd, J = 3.6, 1.1 Hz, 1H), 6.64 (dd, J = 8.9, 2.6 Hz, 1H), 6.56 (d, J= 2.6 Hz, 1H), 3.90 – 3.88(m, 7H), 3.17 – 3.14 (m, 4H), 2.60 (d, J = 1.1 Hz, 3H). 13 C NMR (100 MHz, CDCl3) δ 149.33, 147.35, 146.36, 144.59, 141.07, 140.45, 138.55, 137.30,129.59, 128.59, 127.01, 126.46, 126.30, 125.32, 123.06, 119.88, 108.07,100.13, 67.08, 55.96, 50.55, 15.64. HRMS (ESI) calcd for C 24 H 24 N4O2S[M + H] + ,433.1693; found, 433.1687. HPLC retention time = 5.239 min, purity = 98.40%, ( l = 254nm).

[0101] Example 40

[0102] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-40. The preparation method of compound I-40 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 2-thiopheneboronic acid. The yield of compound I-40 obtained is 51.3%. The structure of compound I-40 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 8.9 Hz, 1H), 8.28 (s, 1H), 7.90(d, J = 6.7 Hz, 1H), 7.84 (d, J = 3.8 Hz, 1H), 7.79 (d, J = 6.8 Hz, 1H), 7.60(d, J = 5.1 Hz, 1H), 7.56 (dd, J = 8.3, 1.4 Hz, 1H), 7.44 – 7.40 (m, 1H), 7.24 – 7.23 (m, 1H), 6.63 (dd, J= 8.8, 2.7 Hz, 1H), 6.55 (d, J = 2.6 Hz,1H), 3.90 – 3.88 (m, 7H), 3.16 – 3.14 (m, 4H). 13 C NMR (100 MHz, CDCl3) δ149.34, 147.42, 146.48, 140.93, 140.80, 140.71, 137.27, 129.90, 129.44,128.72, 127.94, 126.91, 126.53, 125.40, 122.94, 119.88, 108.03, 100.09,67.08, 55.96, 50.51. HRMS (ESI) calcd for C 23 H 22 N4O2S[M + H] + , 419.1536; found, 419.1523. HPLC retention time = 5.230 min, purity = 96.68%, ( l = 254 nm).

[0103] Example 41

[0104] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-41. The preparation method of compound I-41 is basically the same as in Example 39, except that 5-methylthiophene-2-boric acid is replaced with benzothiophene-2-boric acid. The yield of compound I-41 obtained is 63.5%. The structure of compound I-41 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 8.8 Hz, 1H), 8.41 (s, 1H), 8.14 (s, 1H), 7.95 (d, J = 1.5 Hz, 1H), 7.94 (s, 1H), 7.90 – 7.87 (m, 1H), 7.81 (d, J = 7.2 Hz, 1H), 7.62 – 7.58 (m, 1H), 7.46 – 7.43 (m, 3H), 6.65 (dd, J = 8.8, 2.6 Hz, 1H), 6.57 (d, J= 2.5 Hz, 1H), 3.91 – 3.89 (m, 7H), 3.18-3.15 (m, 4H). 13 C NMR (100 MHz, CDCl3) δ 149.39, 147.53, 146.55, 141.37,140.96, 140.84, 140.71, 140.28, 137.34, 130.31, 128.89, 126.59, HRMS (ESI) calcd for C 27 H 24 N4O2S[M + H] + , 469.1693; found, 469.1674. HPLC retention time = 5.615 min, purity = 96.75%, ( l = 254 nm).

[0105] Example 42

[0106] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-42. The preparation method of compound I-42 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 2-furanboronic acid. The yield of compound I-42 obtained is 65.1%. The structure of compound I-42 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 9.19 (s, 1H), 8.91 (d, J = 8.7 Hz, 1H), 7.89(d, J = 9.2 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.72 (s, 1H), 7.56 (t, J = 7.0Hz, 1H), 7.42 – 7.39 (m, 2H), 6.69 (d, J = 1.8 Hz, 1H), 6.63 (d, J = 9.0 Hz, 1H), 6.59 (d, J= 2.6 Hz, 1H), 3.96 (s, 3H), 3.91 – 3.88 (m, 4H), 3.17 – 3.15 (m, 4H). 13 C NMR (100 MHz, CDCl3) δ 152.09, 149.56, 147.32, 146.09, 143.84,140.66, 136.88, 135.89, 129.79, 128.64, 126.46, 125.35, 123.33, 120.19,113.08, 112.52, 108.07, 100.31, 67.10, 56.18, 50.54. HRMS (ESI) calcd forC 23 H 22 N4O3[M + H] + , 403.1765; found, 403.1756. HPLC retention time = 4.940 min, purity = 98.56% ( l =254 nm).

[0107] Example 43

[0108] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-43. The preparation method of compound I-43 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 1H-pyrazole-4-boronic acid. The yield of compound I-43 obtained is 64.8%. The structure of compound I-43 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.89 (d, J = 8.9 Hz, 1H), 8.29 (s, 2H), 7.98 (s, 1H), 7.89 (d, J = 7.9 Hz, 1H), 7.81 (d, J = 6.9 Hz, 1H), 7.60 – 7.56(m, 1H), 7.45-7.41 (m, 1H), 6.65 (dd, J = 9.0, 2.4 Hz, 1H), 6.56 (d, J = 2.5Hz, 1H), 3.91 – 3.89 (m, 7H), 3.17-3.15 (m, 4H). 13C NMR (100 MHz, CDCl3) δ149.22, 147.40, 147.20, 140.65, 137.44, 129.55, 128.43, 126.64, 125.36,122.94, 119.81, 118.83, 108.06, 100.05, 67.08, 55.95, 50.53. HRMS (ESI) calcdfor C 22 H 22 N6O2[M + H] + , 403.1877; found, 403.1871. HPLC retention time = 4.310 min, purity = 96.66%, ( l = 254 nm).

[0109] Example 44

[0110] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-44. The preparation method of compound I-44 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 1-methyl-1H-pyrazole-4-boronic acid. The yield of compound I-44 is 69.8%. The structure of compound I-44 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.90 (d, J = 7.0 Hz, 1H), 8.16(s, 1H), 8.09 (s, 1H), 8.02 (s, 1H), 7.85 (d, J = 7.4 Hz, 1H), 7.80 (d, J =8.4 Hz, 1H), 7.56 (t, J = 7.4 Hz, 1H), 7.41 (t, J = 6.9 Hz, 1H), 6.64 (d, J =9.2 Hz, 1H), 6.57 (s, 1H), 4.05 (s, 3H), 3.91 (s, 4H), 3.89 (s, 3H), 3.16 (s, 4H). 13C NMR (100 MHz, CDCl3) δ 149.21, 147.34, 147.08, 140.67, 140.54,138.43, 137.45, 131.31, 129.35, 128.37, 126.61, 125.26, 123.03, 119.74,119.32, 108.05, 100.04, 67.08, 55.93, 50.54, 39.46. HRMS (ESI) calcd forC 23 H 24 N6O2[M + H] + , 417.2034; found, 417.2017. HPLC retention time = 4.422 min, purity = 95.72% ( l = 254 nm).

[0111] Example 45

[0112] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-45. The preparation method of compound I-45 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with phenylboronic acid. The yield of compound I-45 is 50.5%. The structure of compound I-45 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 8.8 Hz, 1H), 7.94 (d, J = 8.0 Hz,1H), 7.85 – 7.79 (m, 4H), 7.62 – 7.54 (m, 4H), 7.45 – 7.41 (m, 1H), 6.62 (dd, J = 8.8, 2.5 Hz, 1H), 6.50 (d, J = 2.6 Hz, 1H), 3.89 – 3.87 (m, 4H), 3.75 (s, 3H), 3.15 – 3.12 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 149.25, 147.84, 147.42,147.33, 141.25, 137.40, 136.67, 129.89, 129.83, 129.36, 128.91, 128.76,126.63, 125.18, 123.06, 119.54, 108.01, 100.14, 67.07, 55.85, 50.53. HRMS(ESI) calcd for C 25 H 24 N4O2[M + H] + , 413.1972; found, 413.1973. HPLC retention time = 4.773 min, purity = 97.62%, ( l = 254 nm).

[0113] Example 46

[0114] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-46. The preparation method of compound I-46 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with pyridine-3-boronic acid. The yield of compound I-46 obtained is 63.8%. The structure of compound I-46 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 9.10 (s, 1H), 8.82 (d, J = 8.8 Hz, 2H), 8.16 (d, J = 6.5 Hz, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 7.5 Hz, 1H),7.65-7.61 (m, 2H), 7.53 (s, 1H), 7.45 (t, J = 7.5 Hz, 1H), 6.62 (d, J = 8.5Hz, 1H), 6.51 (s, 1H), 3.88 (s, 4H), 3.77 (s, 3H), 3.14 (s, 4H). 13C NMR (100MHz, CDCl3) δ 150.91, 149.84, 149.28, 147.60, 147.35, 144.65, 141.40, 137.53,136.49, 132.84, 130.38, 128.97, 126.78, 125.53, 123.83, 122.60, 119.86,107.92, 99.96, 67.05, 55.89, 50.42. HRMS (ESI) calcd for C 24 H 23 N5O2[M+H] + ,414.1925; found, 414.1904. HPLC retention time = 4.420 min, purity = 96.18%, ( l =254=nm).

[0115] Example 47

[0116] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-47. The preparation method of compound I-47 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 5-pyrimidineboronic acid. The yield of compound I-47 was 47.3%. The structure of compound I-47 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 9.41 (s, 1H), 9.26 (s, 2H), 8.74 (d, J = 8.5Hz, 1H), 7.93 (d, J = 8.4 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.68 – 7.64 (m,1H), 7.50 – 7.46 (m, 2H), 6.62 (d, J = 8.8 Hz, 1H), 6.52 (s, 1H), 3.88 (s, 4H), 3.81 (s, 3H), 3.15 (s, 4H). 13C NMR (100 MHz, CDCl3) δ 159.35, 157.02,149.33, 147.86, 147.23, 141.54, 141.41, 137.70, 131.24, 130.93, 129.07,126.90, 125.88, 122.16, 120.13, 107.82, 99.81, 67.03, 55.92, 50.32. HRMS(ESI) calcd for C 23 H 22 N6O2[M + H] + , 415.1877; found, 415.1877. HPLC retention time = 4.311 min, purity = 97.21%, ( l = 254 nm).

[0117] Example 48

[0118] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-48. The preparation method of compound I-48 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 5-indoleboronic acid pinacol ester. The yield of compound I-48 was 63.3%. The structure of compound I-48 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, DMSO- d 6) δ 11.42 (s, 1H), 8.70 (d, J = 8.8Hz, 1H), 8.20 (s, 1H), 8.06 (s, 1H), 7.86 (d, J = 8.2 Hz, 1H), 7.74 (d, J =8.3 Hz, 1H), 7.66 (d, J = 8.3 Hz, 1H), 7.62 (t, J = 7.5 Hz, 1H), 7.55 – 7.51(m, 2H), 7.45 (t, J = 6.8 Hz, 1H), 6.66 (d, J = 2.6 Hz, 1H), 6.63 (s, 1H), 6.58 (dd, J= 9.1, 2.6 Hz, 1H), 3.76-3.73 (m, 4H), 3.69 (s, 3H), 3.11-3.08(m, 4H). 13 C NMR (100 MHz, DMSO- d 6) δ 149.67, 149.44, 147.82, 147.77, 140.70,137.46, 137.05, 129.95, 128.88, 128.41, 127.52, 127.11, 126.42, 125.38,122.14, 122.08, 121.07, 119.72, 112.73, 107.18, 102.38, 100.36, 66.68, 56.62,49.66. HRMS (ESI) calcd for C 27 H 25 N8O2[M + H] + , 452.2081; found, 452.2079. HPLC retention time = 4.595 min, purity = 97.65%, ( l = 254 nm).

[0119] Example 49

[0120] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-49. The preparation method of compound I-49 is basically the same as that of Example 39, except that 5-methylthiophene-2-boronic acid is replaced with benzo[C][1,2,5]diazole-5-boronic acid pinacol ester. The yield of compound I-49 was 36.3%. The structure of compound I-49 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.79 (d, J = 8.5 Hz,1H), 8.46 (s, 1H), 8.08 (d, J = 8.8 Hz, 1H), 7.93 (d, J = 7.5 Hz, 1H), 7.85(d, J = 8.8 Hz, 1H), 7.73 (s, 1H), 7.66 (t, J = 8.0 Hz, 1H), 7.48 (t, J = 7.7Hz, 1H), 6.62 (d, J= 9.0 Hz, 1H), 6.51 (s, 1H), 3.89 (s, 4H), 3.77 (s, 3H), 3.15 (s, 4H). 13 C NMR (100 MHz, CDCl3) δ 149.43, 149.21, 149.00, 147.81,146.89, 144.34, 141.48, 140.16, 137.30, 133.26, 130.91, 129.05, 126.83,125.80, 122.24, 120.11, 117.94, 116.50, 107.86, 99.85, 67.03, 55.89, 50.34.HRMS (ESI) calcd for C 25 H 22 N6O3[M + H] + , 455.1826; found, 455.1820. HPLC retention time = 4.645 min, purity = 98.28%, ( l = 254 nm).

[0121] Example 50

[0122] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-50. The preparation method of compound I-50 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 3,4-methylenephenylboronic acid. The yield of compound I-50 obtained was 58.0%. The structure of compound I-50 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.85 (d, J = 8.7 Hz, 1H), 7.90 (d, J = 7.5 Hz, 2H), 7.81 (d, J = 9.9 Hz, 1H), 7.58 (t, J = 7.4 Hz, 1H), 7.41 (t, J = 8.2 Hz, 1H), 7.34 (d, J = 8.0 Hz, 1H), 7.30 (s, 1H), 7.00 (d, J = 8.0 Hz, 1H), 6.62 (d, J= 7.5 Hz, 1H), 6.52 (s, 1H), 6.08 (s, 2H), 3.88 (s, 4H), 3.81 (s, 3H), 3.14 (s, 4H). 13 C NMR (100 MHz, CDCl3) δ 149.36, 149.06, 148.69,147.37, 147.34, 147.16, 141.07, 137.35, 130.52, 129.73, 128.78, HRMS (ESI) calcd for C 26 H 24 N4O4[M + H] + , 457.1870; found, 457.1873. HPLC retention time = 4.764 min, purity = 95.46%, ( l = 254 nm).

[0123] Example 51

[0124] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-51. The preparation method of compound I-51 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with (2,2-difluorobenzo[D][1,3]dioxacyclopenten-5-yl)boronic acid. The yield of compound I-51 obtained was 55.1%. The structure of compound I-51 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.82 (d, J =8.5 Hz, 1H), 7.90 (d, J = 8.3 Hz, 1H), 7.83 (d, J = 7.5 Hz, 1H), 7.73 (s,1H), 7.60 (d, J = 10.5 Hz, 3H), 7.44 (t, J = 8.0 Hz, 1H), 7.28 (s, 1H), 6.62(d, J= 9.5 Hz, 1H), 6.52 (s, 1H), 3.88 (s, 4H), 3.80 (s, 3H), 3.14 (s, 4H). 13 C NMR (100 MHz, CDCl3) δ 149.29, 147.56, 147.07, 145.79, 144.81, 144.59,141.26, 137.32, 132.87, 130.23, 128.87, 126.68, 125.48, 124.49, 122.62,119.79, 110.75, 110.06, 107.93, 99.96, 67.05, 55.88, 50.44. HRMS (ESI) calcdfor C 26 H 22 F2N4O4[M + H] + , 493.1682; found, 493.1680. HPLC retention time = 4.938 min, purity = 95.39% ( l = 254 nm).

[0125] Example 52

[0126] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-52. The preparation method of compound I-52 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with benzo-1,4-dioxane-6-boronic acid. The yield of compound I-52 obtained is 56.4%. The structure of compound I-52 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.84 (d, J = 8.9 Hz, 1H), 7.96(s, 1H), 7.90 (dd, J = 8.2, 1.3 Hz, 1H), 7.80 (dd, J = 8.3, 1.3 Hz, 1H),7.59-7.54 (m, 1H), 7.42-7.38 (m, 1H), 7.37 (d, J = 2.1 Hz, 1H), 7.31 (dd, J =8.3, 2.1 Hz, 1H), 7.05 (d, J = 8.3 Hz, 1H), 6.61 (dd, J= 8.9, 2.6 Hz, 1H), 6.51 (d, J = 2.6 Hz, 1H), 4.36 – 4.31 (m, 4H), 3.88 – 3.86 (m, 4H), 3.81 (s, 3H), 3.14 – 3.12 (m, 4H). 13 C NMR (100 MHz, CDCl3) δ 149.41, 147.37, 147.33,147.13, 145.16, 144.39, 141.07, 137.41, 129.92, 129.62, 128.82, HRMS (ESI) calcd for C 27 H 26 N4O4[M + H] + , 471.2027; found,471.2024. HPLC retention time = 4.886 min, purity = 95.12%, ( l = 254nm).

[0127] Example 53

[0128] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-53. The preparation method of compound I-53 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with quinoline-3-boronic acid. The yield of compound I-53 obtained is 64.0%. The structure of compound I-53 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 9.38 (s, 1H), 8.84 (d, J = 9.2 Hz, 1H),8.71 (s, 1H), 8.24 (d, J = 8.7 Hz, 1H), 7.96 (t, J = 7.7 Hz, 2H), 7.87-7.83(m, 2H), 7.77 (s, 1H), 7.65 (q, J = 8.1 Hz, 2H), 7.47 (t, J = 7.5 Hz, 1H), 6.63 (d,J = 8.8 Hz, 1H), 6.49 (s, 1H), 3.87 (s, 4H), 3.69 (s, 3H), 3.13 (s, 4H). 13 C NMR (100 MHz, CDCl3) δ 150.54, 149.34, 148.49, 147.61, 147.50,144.59, 141.34, 137.71, 135.96, 130.81, 130.39, 129.75, HRMS (ESI) calcd for C 28 H 25 N5O2[M + H] + , 464.2081; found,464.2091. HPLC retention time = 4.759 min, purity = 98.15%, ( l = 254 nm).

[0129] Example 54

[0130] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-54. The preparation method of compound I-54 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-indoleboronic acid pinacol ester. The yield of compound I-54 was 53.9%. The structure of compound I-54 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, DMSO- d 6) δ 12.01 (s, 1H), 8.54 (d, J = 10.4Hz, 1H), 8.48 (s, 1H), 7.91 (d, J = 8.2 Hz, 1H), 7.82 (s, 1H), 7.78 (d, J =8.0 Hz, 1H), 7.69 (t, J = 7.7 Hz, 1H), 7.63 (s, 1H), 7.52-7.48 (m, 1H), 7.45(s, 1H), 6.61 (s, 1H), 6.56 (d, J= 8.5 Hz, 1H), 6.44 (s, 1H), 3.74 (s, 4H), 3.57 (s, 3H), 3.09 (s, 4H). 13 C NMR (100 MHz, DMSO- d 6) δ 150.06, 149.77,148.14, 147.61, 145.94, 143.46, 141.28, 137.11, 135.40, 130.89, 129.21,128.09, 126.62, 125.67, 121.76, 120.39, 118.15, 115.62, 107.16, 100.41,99.88, 66.67, 56.41, 49.59. HRMS (ESI) calcd for C 26 H 24 N6O2[M + H] + , 453.2034;found, 453.2024. HPLC retention time = 4.394 min, purity = 97.98%, ( l = 254 nm).

[0131] Example 55

[0132] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-55. The preparation method of compound I-55 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-acetylphenylboronic acid. The yield of compound I-55 was 57.2%. The structure of compound I-55 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.83 (d, J = 8.8 Hz, 1H), 8.18 (s, 1H), 8.16 (s, 1H), 7.95 (s, 1H), 7.92 (d, J = 7.5 Hz, 2H), 7.83 (d, J = 8.4 Hz,1H), 7.69 (s, 1H), 7.61 (t, J = 6.9 Hz, 1H), 7.44 (t, J = 6.8 Hz, 1H), 6.61(dd, J = 8.9, 2.6 Hz, 1H), 6.50 (d, J= 2.6 Hz, 1H), 3.88 – 3.86 (m, 4H), 3.75 (s, 3H), 3.14 – 3.12 (m, 4H), 2.69 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ197.58, 149.31, 147.56, 147.13, 146.34, 141.37, 137.98, 137.44, 130.27,129.20, 129.00, 126.72, 125.42, 122.70, 119.87, 107.96, 100.03, 67.04, 55.93,50.42, 26.88. HRMS (ESI) calcd for C 27 H 26 N4O3[M + H] + , 455.2078; found,455.2073. HPLC retention time = 4.632 min, purity = 95.49%, ( l = 254 nm).

[0133] Example 56

[0134] This embodiment provides a quinoxaline compound with general formula I, specifically compound I-56. The preparation method of compound I-56 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-carbamoylphenylboronic acid. The yield of compound I-56 obtained is 54.8%. The structure of compound I-56 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.82 (d, J = 8.8 Hz, 1H), 8.05 (s,1H), 8.03 (s, 1H), 7.94 – 7.91 (m, 3H), 7.83 (d, J = 8.4 Hz, 1H), 7.68 (s,1H), 7.64 – 7.60 (m, 1H), 7.46 – 7.42 (m, 1H), 6.62 (dd, J = 8.7, 2.7 Hz, 1H), 6.50 (d, J = 2.8 Hz, 1H), 3.89-3.86 (m, 4H), 3.76 (s, 3H), 3.15-3.12 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 168.60, 149.33, 147.57, 147.17, 146.37,141.37, 140.43, 137.42, 134.50, 130.24, 129.23, 128.95, 128.34, 126.73,125.42, 122.69, 119.88, 107.95, 100.05, 67.04, 55.94, 50.44. HRMS (ESI) calcdfor C 26 H 25 N5O3[M + H] + , 456.2030; found, 456.2025. HPLC retention time = 4.280 min, purity = 97.45%, ( l = 254 nm).

[0135] Example 57 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-57. The preparation method of compound I-57 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-(methanesulfonyl)phenylboronic acid. The yield of compound I-57 was 69.4%. The structure of compound I-57 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.80 (d, J = 9.0 Hz, 1H), 8.19 (s,1H), 8.17 (s, 1H), 8.08 (s, 1H), 8.06 (s, 1H), 7.92 (d, J = 9.5 Hz, 1H), 7.85(d, J = 8.3 Hz, 1H), 7.65 (t, J = 7.2 Hz, 1H), 7.57 (s, 1H), 7.46 (t, J = 7.4Hz, 1H), 6.62 (d, J = 8.8 Hz, 1H), 6.51 (s, 1H), 3.88 (s, 4H), 3.77 (s, 3H), 3.16 – 3.13 (m, 4H), 3.13 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 149.31, 147.72,146.99, 145.36, 142.41, 141.73, 141.52, 137.39, 130.62, 130.04, 129.01,128.44, 126.81, 125.64, 122.39, 119.96, 107.86, 99.91, 67.04, 55.94, 50.37,44.65. HRMS (ESI) calcd for C 26 H 26 N4O4S[M + H] + , 491.1748; found, 491.1746.HPLC retention time = 4.308 min, purity = 97.37%, ( l = 254 nm).

[0136] Example 58 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-58. The preparation method of compound I-58 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)benzenesulfonyl fluoride. The yield of compound I-58 was 21.6%. The structure of compound I-58 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.77(d, J = 8.9 Hz, 1H), 8.23 ​​(d, J = 2.0 Hz, 1H), 8.22 (d, J = 2.0 Hz, 1H), 8.13(s, 1H), 8.11 (s, 1H), 7.91 (dd, J = 8.3, 1.5 Hz, 1H), 7.84 (dd, J = 8.4, 1.5Hz, 1H), 7.67-7.62 (m, 1H), 7.50 (s, 1H), 7.48-7.44 (m, 1H), 6.61 (dd, J =8.9, 2.6 Hz, 1H), 6.50 (d, J= 2.6 Hz, 1H), 3.88 – 3.86 (m, 4H), 3.77 (s, 3H), 3.15 – 3.13 (m, 4H). 13 C NMR (100 MHz, CDCl3) δ 149.28, 147.80, 146.85,144.53, 144.32, 141.58, 137.44, 133.93, 130.87, 130.33, 129.34, 129.10,126.84, 125.80, 122.27, 120.04, 107.89, 99.87, 67.03, 55.91, 50.34. HRMS(ESI) calcd for C 25 H 23 FN4O4S[M + H] + , 495.1497; found, 495.1492. HPLC retention time = 4.650 min, purity = 97.72%, ( l = 254 nm).

[0137] Example 59 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-59. The preparation method of compound I-59 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-(aminosulfonyl)phenylboronic acid. The yield of compound I-59 was 37.2%. The structure of compound I-59 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, DMSO- d 6) δ 8.46 (d, J = 9.9 Hz, 1H), 8.06(s, 2H), 8.03 (s, 2H), 7.88 (d, J = 8.7 Hz, 1H), 7.81 (s, 1H), 7.73 (d, J =8.2 Hz, 1H), 7.66 (s, 1H), 7.56 (s, 2H), 7.47 (s, 1H), 6.67 (s, 1H), 6.57 (d, J = 8.4 Hz, 1H), 3.74 (s, 7H), 3.10 (s, 4H). 13 C NMR (100 MHz, DMSO- d6) δ150.36, 148.30, 147.75, 146.78, 145.73, 141.27, 139.91, 137.20, 130.85,129.96, 129.11, 126.91, 126.58, 125.70, 121.75, 120.82, 107.13, 100.37,66.69, 56.62, 49.58. HRMS (ESI) calcd for C 25 H 25 N5O4S[M + H] + , 492.1700; found,492.1701. HPLC retention time = 4.253 min, purity = 98.23%, ( l = 254 nm).

[0138] Example 60 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-60. The preparation method of compound I-60 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-dimethylaminophenylboronic acid. The yield of compound I-60 obtained is 57.1%. The structure of compound I-60 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.90 (d, J = 8.8 Hz, 1H), 8.05 (s,1H), 7.90 (d, J = 8.4 Hz, 1H), 7.79 (d, J = 9.7 Hz, 1H), 7.76 (s, 1H), 7.74(s, 1H), 7.54 (t, J = 8.3 Hz, 1H), 7.39 (t, J = 8.0 Hz, 1H), 6.87 (s, 1H), 6.86 (s, 1H), 6.62 (d, J = 9.2 Hz, 1H), 6.52 (s, 1H), 3.88 (s, 4H), 3.79 (s, 3H), 3.13 (s, 4H), 3.05 (s, 6H). 13C NMR (100 MHz, CDCl3) δ 151.52, 149.35,148.19, 147.62, 147.16, 140.73, 137.70, 129.79, 129.05, 128.63, 126.44,124.90, 124.01, 123.34, 119.63, 112.51, 108.07, 100.24, 67.10, 55.94, 50.60,40.48. HRMS (ESI) calcd for C 27 H 29 N5O2[M + H] + , 456.2394; found, 456.2394. HPLC retention time = 4.592 min, purity = 97.58%, ( l = 254 nm).

[0139] Example 61 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-61. The preparation method of compound I-61 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-(4-methyl-1-piperazinyl)phenylboronic acid. The yield of compound I-61 was 57.2%. The structure of compound I-61 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 8.9 Hz, 1H),7.96 (s, 1H), 7.91 (d, J = 9.8 Hz, 1H), 7.80 (d, J = 8.3 Hz, 1H), 7.76 (s,1H), 7.74 (s, 1H), 7.56 (t, J = 7.9 Hz, 1H), 7.40 (t, J = 7.9 Hz, 1H), 7.10(s, 1H), 7.08 (s, 1H), 6.62 (d, J = 9.0 Hz, 1H), 6.51 (s, 1H), 3.88 (s, 4H), 3.78 (s, 3H), 3.34 (s, 4H), 3.13 (s, 4H), 2.62 (s, 4H), 2.38 (s, 3H). 13C NMR(100 MHz, CDCl3) δ 152.35, 149.31, 147.80, 147.54, 147.24, 140.88, 137.60,129.79, 129.33, 128.72, 127.12, 126.50, 125.00, 123.19, 119.64, 115.94,108.04, 100.18, 67.08, 55.92, 54.97, 50.56, 48.57, 46.27. HRMS (ESI) calcdfor C 30 H 34 N6O2[M + H] + , 511.2816; found, 511.2817. HPLC retention time = 4.576 min, purity = 98.02%, ( l = 254 nm).

[0140] Example 62 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-62. The preparation method of compound I-62 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-aminophenylboronic acid. The yield of compound I-62 obtained is 50.2%. The structure of compound I-62 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 8.8 Hz, 1H), 7.95 (s, 1H), 7.90 (d, J = 7.7 Hz, 1H), 7.80 (d, J = 8.9 Hz, 1H), 7.66 (s, 1H), 7.64 (s,1H), 7.56 (t, J = 7.5 Hz, 1H), 7.40 (t, J = 7.2 Hz, 1H), 6.85 (d, J = 8.2 Hz, 1H), 6.62 (d, J = 8.8 Hz, 1H), 6.52 (s, 1H), 3.94 (s, 2H), 3.88 (s, 4H), 3.79 (s, 3H), 3.13 (s, 4H). 13C NMR (100 MHz, CDCl3) δ 149.33, 148.08, 148.00,147.56, 147.23, 140.85, 137.56, 130.10, 129.28, 128.67, 126.49, 124.98,123.22, 119.64, 115.39, 108.05, 100.21, 67.09, 55.93, 50.58. HRMS (ESI) calcdfor C 25 H 25 N5O2[M + H] + , 428.2081; found, 428.2076. HPLC retention time = 4.328 min, purity = 95.18%, ( l = 254 nm).

[0141] Example 63 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-63. The preparation method of compound I-63 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-morpholinophenylboronic acid. The yield of compound I-63 obtained is 63.7%. The structure of compound I-63 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 12.0 Hz, 1H), 7.94 (s, 1H), 7.91 (d, J = 8.2 Hz, 1H), 7.81 (d, J = 8.3 Hz, 1H), 7.78 (s, 1H), 7.76 (s,1H), 7.56 (t, J = 7.8 Hz, 1H), 7.40 (t, J = 7.6 Hz, 1H), 7.08 (s, 1H), 7.07(s, 1H), 6.62 (d, J = 9.3 Hz, 1H), 6.51 (s, 1H), 3.89 (s, 8H), 3.78 (s, 3H), 3.27 (s, 4H), 3.13 (s, 4H). 13C NMR (100 MHz, CDCl3) δ 152.40, 149.31, 147.67,147.52, 147.27, 140.91, 137.59, 129.87, 129.41, 128.72, 127.59, 126.53,125.05, 123.14, 119.70, 115.65, 108.04, 100.18, 67.08, 66.83, 55.94, 50.54,48.79. HRMS (ESI) calcd for C 29 H 31 N5O3[M + H] + , 498.2500; found, 498.2494. HPLC retention time = 4.731 min, purity = 98.33%, ( l = 254 nm).

[0142] Example 64 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-64. The preparation method of compound I-64 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-acetamidophenylboronic acid. The yield of compound I-64 was 56.3%. The structure of compound I-64 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.83 (d, J = 8.8 Hz, 1H), 7.91 (d, J = 8.4 Hz, 1H), 7.83 (s, 1H), 7.81 (d, J = 2.5 Hz, 1H), 7.79 (s, 1H), 7.74 (d, J = 8.4 Hz, 2H), 7.58 (t, J = 7.6 Hz, 1H), 7.54 (s, 1H), 7.41 (t, J = 6.8 Hz, 1H), 6.61 (dd, J = 8.8, 2.6 Hz, 1H), 6.50 (d, J = 2.5 Hz, 1H), 3.88 – 3.86 (m, 4H), 3.78 (s, 3H), 3.14 – 3.12 (m, 4H), 2.22 (s, 3H).13 C NMR (100 MHz, CDCl3) δ 168.55, 149.41, 147.43, 147.13, 141.17, 139.46, 137.46, 132.36,129.76, 129.65, 128.76, 126.61, 125.17, 122.93, 120.21, 119.80, 107.98,100.13, 67.06, 55.93, 50.48, 24.81. HRMS (ESI) calcd for C 27 H 27 N5O3[M + H] + ,470.2187 ; found, 470.2178. HPLC retention time = 4.452 min, purity = 95.11%, ( l =254 nm).

[0143] Example 65 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-65. The preparation method of compound I-65 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-(urea)phenylboronic acid pinacol ester. The yield of compound I-65 was 47.3%. The structure of compound I-65 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, DMSO- d 6) δ 8.87 (s, 1H), 8.62 (d, J = 8.8Hz, 1H), 7.98 (s, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.73 – 7.66 (m, 5H), 7.61(t, J = 7.0 Hz, 1H), 7.45 (t, J = 7.5 Hz, 1H), 6.68 (d, J = 2.5 Hz, 1H), 6.58 (dd, J = 9.2, 2.6 Hz, 1H), 5.99 (s, 2H), 3.77 (s, 3H), 3.76-3.74 (m, 4H), 3.12 – 3.09 (m, 4H). 13 C NMR (100 MHz, DMSO- d6) δ 156.39, 149.88, 147.93,147.69, 142.79, 140.78, 137.38, 130.12, 129.70, 128.91, 126.43, 125.45,122.04, 120.11, 118.35, 107.20, 100.41, 66.70, 56.69, 49.66. HRMS (ESI) calcdfor C 26 H 26 N6O3[M + H] + , 471.2139; found, 471.2144. HPLC retention time = 4.270 min, purity = 95.63%, ( l = 254 nm).

[0144] Example 66 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-66. The preparation method of compound I-66 is basically the same as that in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-( N -Boc-amino)phenylboronic acid. The yield of compound I-66 obtained was 47.1%. The structure of compound I-66 was analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ8.85(d, J = 8.5Hz, 1H), 7.91 (d, J =7.9 Hz,1H),7.86(s,1H), 7.80(t, J = 9.9 Hz, 3H), 7.59 (d, J = 8.4 Hz, 3H), 7.41(t, J = 7.5 Hz,1H), 6.76(s,1H), 6.62(d, J =8.9 Hz,1H), 6.51 (s, 1H), 3.88 (s,4H), 3.79 (s, 3H), 3.14 (s, 4H), 1.55 (s,9H). 13C NMR (100MHz, CDCl3) δ152.58,149.40, 147.44, 147.36, 147.30, 141.06,140.02,137.48,131.05,129.68,129.65,128.77,126.57,125.13,122.99,119.79,118.77,107.96, 100.15, 81.08, 67.08,55.97, 50.53, 28.45. HRMS (ESI) calcd for C 30 H 33 N5O4[M+H] + , 528.2605; found, 528.2600. HPLC retention time = 4.806 min, purity = 97.91%, ( l =254nm).

[0145] Example 67 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-67. The preparation method of compound I-67 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-methylsulfonylaminophenylboronic acid. The yield of compound I-67 was 53.8%. The structure of compound I-67 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.83 (d, J = 8.9 Hz, 1H), 7.91(d, J = 8.2 Hz, 1H), 7.83 (d, J = 8.7 Hz, 3H), 7.75 (s, 1H), 7.60 (t, J = 7.7Hz, 1H), 7.44 (d, J = 8.5 Hz, 3H), 7.29 (s, 1H), 6.61 (dd, J = 8.8, 2.6 Hz, 1H), 6.50 (d, J = 2.6 Hz, 1H), 3.89 – 3.87 (m, 4H), 3.77 (s, 3H), 3.15 – 3.12(m, 4H), 3.09 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 149.32, 147.49, 147.33,146.66, 141.26, 138.49, 137.39, 133.41, 130.41, 130.00, 128.78, 126.67,125.33, 122.81, 120.61, 119.79, 108.01, 100.09, 67.05, 55.94, 50.44, 39.77.HRMS (ESI) calcd for C 26 H 27 N5O4S [M + H] + , 506.1862; found, 506.1857. HPLC retention time = 4.338 min, purity = 96.68%, ( l = 254 nm).

[0146] Example 68 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-68. The preparation method of compound I-68 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-tolueneboronic acid. The yield of compound I-68 was 67.1%. The structure of compound I-68 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.87 (d, J = 8.9 Hz, 1H), 7.92 (d, J = 9.3Hz, 1H), 7.87 (s, 1H), 7.82 (d, J = 8.0 Hz, 1H), 7.72 (s, 1H), 7.70 (s, 1H), 7.58 (t, J = 7.8 Hz, 1H), 7.43 – 7.38 (m, 3H), 6.62 (d, J = 9.3 Hz, 1H), 6.50(s, 1H), 3.88 (s, 4H), 3.77 (s, 3H), 3.13 (s, 4H), 2.47 (s, 3H). 13C NMR (100MHz, CDCl3) δ 149.32, 147.90, 147.48, 147.31, 141.13, 139.97, 137.47, 133.81,129.98, 129.65, 128.86, 128.65, 126.58, 125.09, 123.11, 119.64, 108.03,100.18, 67.08, 55.91, 50.54, 21.59. HRMS (ESI) calcd for C 26 H 26 N4O2[M + H] + ,427.2129; found, 427.2144. HPLC retention time = 5.103 min, purity = 95.41%, ( l =254nm).

[0147] Example 69 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-69. The preparation method of compound I-69 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-tert-butylphenylboronic acid. The yield of compound I-69 obtained is 61.3%. The structure of compound I-69 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 9.0 Hz, 1H), 7.94 – 7.90(m, 2H), 7.83 (d, J = 9.0 Hz, 1H), 7.75 (s, 1H), 7.73 (s, 1H), 7.62-7.57 (m,3H), 7.42 (t, J = 7.9 Hz, 1H), 6.62 (d, J = 9.4 Hz, 1H), 6.50 (s, 1H), 3.87(s, 4H), 3.74 (s, 3H), 3.13 (s, 4H), 1.40 (s, 9H). 13C NMR (100 MHz, CDCl3) δ153.15, 149.23, 148.02, 147.54, 147.26, 141.18, 137.46, 133.73, 129.66,128.89, 128.44, 126.59, 126.30, 125.09, 123.19, 119.48, 108.05, 100.18,67.08, 55.82, 50.55, 34.99, 31.39. HRMS (ESI) calcd for C 29 H 32 N4O2[M + H] + ,469.2598; found, 469.2578. HPLC retention time = 5.476 min, purity = 95.65%, ( l = 254nm).

[0148] Example 70 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-70. The preparation method of compound I-70 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-(trimethylsilane)phenylboronic acid. The yield of compound I-70 obtained is 53.8%. The structure of compound I-70 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.87 (d, J = 9.2 Hz, 1H), 7.93 (d, J = 8.3 Hz, 1H), 7.85 (d, J = 5.9 Hz, 1H), 7.82 (s, 1H), 7.78 (d, J = 6.8 Hz, 2H), 7.74 (d, J = 6.5 Hz, 2H), 7.60 (t, J = 7.4 Hz, 1H), 7.43 (t, J = 7.2 Hz, 1H), 6.62 (d, J = 9.0 Hz, 1H), 6.50 (s, 1H), 3.88 (s, 4H), 3.74 (s, 3H), 3.14(s, 4H). 13C NMR (100 MHz, CDCl3) δ 149.30, 147.88, 147.45, 147.34, 142.81,141.24, 137.47, 136.96, 134.20, 129.77, 128.95, 127.83, 126.61, 125.14,123.11, 119.62, 108.04, 100.19, 67.07, 55.82, 50.53. HRMS (ESI) calcd forC 28 H 32 N4O2Si [M + H] + , 485.2367; found, 485.2362. HPLC retention time = 5.587 min, purity = 97.08%, ( l = 254 nm).

[0149] Example 71 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-71. The preparation method of compound I-71 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-methoxyphenylboronic acid. The yield of compound I-71 obtained is 63.8%. The structure of compound I-71 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.87 (d, J = 8.8 Hz, 1H), 7.91 (d, J =9.7 Hz, 1H), 7.87 (s, 1H), 7.81 (d, J = 8.3 Hz, 1H), 7.79 (s, 1H), 7.76 (s,1H), 7.57 (t, J = 8.4 Hz, 1H), 7.41 (t, J = 6.8 Hz, 1H), 7.11 (s, 1H), 7.09(s, 1H), 6.62 (dd, J = 8.9, 2.5 Hz, 1H), 6.51 (d, J = 2.6 Hz, 1H), 3.91 (s,3H), 3.89 – 3.86 (m, 4H), 3.78 (s, 3H), 3.14 – 3.12 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 160.94, 149.31, 147.56, 147.51, 147.32, 141.05, 137.52, 130.27,129.53, 129.06, 128.78, 126.56, 125.08, 123.13, 119.66, 114.74, 108.07,100.18, 67.07, 55.91, 55.58, 50.54. HRMS (ESI) calcd for C 26 H 26 N4O3[M + H] + ,443.2078; found, 443.2073. HPLC retention time = 4.799 min, purity = 95.90%, ( l = 254nm).

[0150] Example 72 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-72. The preparation method of compound I-72 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-acetoxyphenylboronic acid. The yield of compound I-72 obtained is 63.2%. The structure of compound I-72 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.83 (d, J = 8.8 Hz, 1H), 8.27 (s,1H), 8.25 (s, 1H), 7.93 – 7.90 (m, 3H), 7.83 (d, J = 8.4 Hz, 1H), 7.70 (s,1H), 7.61 (t, J = 6.9 Hz, 1H), 7.43 (t, J = 8.3 Hz, 1H), 6.61 (dd, J = 8.9, 2.6 Hz, 1H), 6.49 (d, J = 2.6 Hz, 1H), 3.99 (s, 3H), 3.88 – 3.86 (m, 4H), 3.75 (s, 3H), 3.14 – 3.11 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 166.62, 149.31,147.53, 147.14, 146.47, 141.38, 141.23, 137.41, 131.35, 130.52, 130.22,128.97, 126.71, 125.39, 122.75, 119.81, 107.96, 100.04, 67.05, 55.92, 52.47,50.44. HRMS (ESI) calcd for C 27 H 26 N4O4[M + H] + , 471.2027; found, 471.2019. HPLC retention time = 4.854 min, purity = 95.11%, ( l = 254 nm).

[0151] Example 73 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-73. The preparation method of compound I-73 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with p-difluoromethoxyphenylboronic acid. The yield of compound I-73 obtained is 59.1%. The structure of compound I-73 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.85 (d, J = 8.9 Hz, 1H), 7.91 (d, J = 8.4 Hz, 1H), 7.83 (d, J = 8.9 Hz, 3H), 7.73 (s, 1H), 7.60 (t, J = 7.3 Hz, 1H), 7.43 (t, J = 7.2 Hz, 1H), 7.35 (s, 1H), 7.33 (s, 1H), 6.80 (s, 0.25H), 6.62 (s, 1H), 6.60 (s, 0.5H), 6.50 (s, 1H), 6.43 (s, 0.25H), 3.88 (s, 4H), 3.76 (s, 3H), 3.13 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 152.18, 149.19, 147.44,147.27, 146.59, 141.27, 137.37, 133.92, 130.60, 130.03, 128.88, HRMS (ESI) calcd for C 26 H 24 F2N4O3[M + H] + , 479.1889;found, 479.1891. HPLC retention time = 4.606 min, purity = 96.89%, ( l = 254 nm).

[0152] Example 74 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-74. The preparation method of compound I-74 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-methylthiophenylboronic acid. The yield of compound I-74 was 59.7%. The structure of compound I-74 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.85 (d, J = 8.9 Hz, 1H), 7.91 (d, J =8.2 Hz, 1H), 7.81 (d, J = 8.4 Hz, 2H), 7.77 (s, 1H), 7.74 (s, 1H), 7.58 (t, J = 8.4 Hz, 1H), 7.45 (s, 1H), 7.43 (s, 1H), 7.40 (d, J = 8.2 Hz, 1H), 6.62(dd, J = 8.8, 2.6 Hz, 1H), 6.50 (d, J = 2.6 Hz, 1H), 3.88 – 3.86 (m, 4H), 3.78 (s, 3H), 3.14 – 3.12 (m, 4H), 2.56 (s, 3H). 13C NMR (100 MHz, CDCl3) δ149.33, 147.41, 147.37, 147.16, 141.22, 141.14, 137.52, 133.24, 129.76,129.17, 128.85, 126.84, 126.61, 125.18, 122.98, 119.78, 108.02, 100.14,67.06, 55.93, 15.65. HRMS (ESI) calcd for C 26 H 26 N4O2S[M + H] + , 459.1849; found,459.1844. HPLC retention time = 4.860 min, purity = 96.01%, ( l = 254 nm).

[0153] Example 75 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-75. The preparation method of compound I-75 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-fluorophenylboronic acid. The yield of compound I-75 was 48.3%. The structure of compound I-75 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.86 (d, J = 8.8 Hz, 1H), 7.91 (d, J = 8.0Hz, 1H), 7.86 – 7.77 (m, 3H), 7.72 (s, 1H), 7.60 (t, J = 7.2 Hz, 1H), 7.43(t, J = 7.4 Hz, 1H), 7.28 (t, J = 8.6 Hz, 2H), 6.62 (dd, J = 8.8, 2.8 Hz, 1H), 6.51 (d, J = 2.5 Hz, 1H), 3.88 – 3.86 (m, 4H), 3.77 (s, 3H), 3.15 – 3.12(m, 4H). 13C NMR (100 MHz, CDCl3) δ 149.23, 147.45, 147.33, 146.69, 141.25,137.40, 130.97, 130.89, 129.94, 128.86, 126.66, 125.29, 122.89, 119.66,116.52, 116.31, 108.02, 100.07, 67.05, 55.89, 50.48. HRMS (ESI) calcd forC 25 H 23 FN4O2[M + H] + , 431.1878; found, 431.1874. HPLC retention time = 4.767 min, purity = 96.82% ( l =254nm).

[0154] Example 76 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-76. The preparation method of compound I-76 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-trifluoromethylphenylboronic acid. The yield of compound I-76 obtained is 44.0%. The structure of compound I-76 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.83 (d, J = 9.0 Hz, 1H), 7.94 (dd, J = 14.6, 8.5 Hz, 3H), 7.85 (t, J = 7.9 Hz, 3H), 7.62 (d, J = 10.8 Hz, 2H), 7.45 (t, J = 6.7 Hz, 1H), 6.62 (d, J = 9.0 Hz, 1H), 6.50 (s, 1H), 3.88 (s, 4H), 3.75 (s, 3H), 3.14 (s, 4H). 13C NMR (100 MHz, CDCl3) δ 149.21, 147.55,147.10, 146.08, 141.42, 140.39, 137.36, 130.37, 129.41, 128.99, 126.75,125.50, 122.64, 119.72, 107.92, 99.96, 67.05, 55.85, 50.43. HRMS (ESI) calcdfor C 26 H 23 F3N4O2[M + H] + , 481.1846; found, 481.1842. HPLC retention time = 4.881 min, purity = 95.14% ( l = 254 nm).

[0155] Example 77 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-77. The preparation method of compound I-77 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-nitrophenylboronic acid. The yield of compound I-77 was 45.3%. The structure of compound I-77 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.81 (d, J = 8.8 Hz, 1H), 8.46 (s, 1H), 8.45 (s, 1H), 8.07 (s, 1H), 8.05 (s, 1H), 7.93 (d, J = 7.9 Hz, 1H), 7.85 (d, J = 8.3 Hz, 1H), 7.65 (t, J = 7.0 Hz, 1H), 7.57 (s, 1H), 7.47 (t, J = 7.2 Hz, 1H), 6.63 (d, J = 8.4 Hz, 1H), 6.51 (s, 1H), 3.89 (s, 4H), 3.78 (s, 3H), 3.15(s, 4H). 13C NMR (100 MHz, CDCl3) δ 149.26, 148.63, 147.71, 146.90, 144.92,143.22, 141.50, 137.39, 130.77, 130.12, 129.05, 126.81, 125.75, 124.49,122.35, 119.97, 107.89, 99.89, 67.04, 55.93, 50.37. HRMS (ESI) calcd forC 25 H 23 N5O4[M + H] + , 458.1823; found, 458.1820. HPLC retention time = 4.607 min, purity = 98.35%, ( l = 254 nm).

[0156] Example 78 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-78. The preparation method of compound I-78 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-cyanophenylboronic acid. The yield of compound I-78 was 47.9%. The structure of compound I-78 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.81 (d, J = 8.8 Hz, 1H), 7.99 (s, 1H), 7.97 (s, 1H), 7.92 – 7.87 (m, 3H), 7.84 (d, J = 8.4 Hz, 1H), 7.63 (t, J = 7.6Hz, 1H), 7.56 (s, 1H), 7.45 (t, J = 7.6 Hz, 1H), 6.62 (dd, J = 9.0, 2.6 Hz, 1H), 6.51 (d, J = 2.6 Hz, 1H), 3.89-3.87 (m, 4H), 3.78 (s, 3H), 3.15-3.13 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 149.24, 147.69, 146.90, 145.28, 141.47,141.41, 137.41, 133.02, 130.60, 129.75, 129.03, 126.78, 125.64, 122.46,119.90, 118.41, 113.64, 107.95, 99.93, 67.03, 55.91, 50.38. HRMS (ESI) calcdfor C 26 H 23 N5O2[M + H] + , 438.1925; found, 438.1908. HPLC retention time = 4.392 min, purity = 95.90%, ( l = 254 nm).

[0157] Example 79 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-79. The preparation method of compound I-79 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-cyano-3-fluorophenylboronic acid. The yield of compound I-79 was 51.4%. The structure of compound I-79 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.76 (d, J = 9.2 Hz, 1H), 7.91 (d, J = 7.8 Hz, 1H), 7.87 – 7.78 (m, 4H), 7.65 (t, J = 7.8 Hz, 1H), 7.56 (s, 1H), 7.47 (t, J = 7.7 Hz, 1H), 6.62 (d, J = 8.7 Hz, 1H), 6.53 (s, 1H), 3.90 – 3.88 (m, 4H), 3.82 (s, 3H), 3.16 – 3.14 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 164.86,162.26, 149.33, 147.81, 146.63, 144.13, 144.05, 143.69, 141.55, 137.33,134.39, 130.99, 129.08, 126.81, 125.86, 125.25, 122.16, 120.08, 117.40,117.19, 113.62, 107.86, 102.70, 102.54, 99.83, 67.03, 55.93, 50.33. HRMS(ESI) calcd for C 26 H 22 FN5O2[M + H] + , 456.1830; found, 456.1828. HPLC retention time = 4.557 min, purity = 95.04%, ( l = 254 nm).

[0158] Example 80 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-80. The preparation method of compound I-80 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 3-fluoro-4-methoxyphenylboronic acid. The yield of compound I-80 obtained is 49.3%. The structure of compound I-80 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.84 (d, J = 8.9 Hz, 1H), 7.91 (d, J = 8.2 Hz, 1H), 7.84 – 7.80 (m, 2H), 7.61 (q, J = 10.4 Hz, 3H), 7.43 (t, J =7.5 Hz, 1H), 7.16 (t, J = 8.6 Hz, 1H), 6.62 (d, J = 9.0 Hz, 1H), 6.52 (s,1H), 4.00 (s, 3H), 3.90-3.87 (m, 4H), 3.82 (s, 3H), 3.15 – 3.13 (m, 4H). 13CNMR (100 MHz, CDCl3) δ 153.87, 151.40, 149.35, 149.17, 149.06, 147.44,147.20, 146.07, 141.13, 137.39, 129.89, 129.51, HRMS (ESI) calcd for C 26 H 25 FN4O3[M + H] + , 461.1983; found, 461.1978. HPLC retention time = 4.763 min, purity = 95.78%, ( l = 254 nm).

[0159] Example 81 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-81. The preparation method of compound I-81 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with 4-cyclopropylphenylboronic acid. The yield of compound I-81 obtained is 66.8%. The structure of compound I-81 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.86 (d, J = 9.3 Hz, 1H), 7.92 (d, J =7.8 Hz, 1H), 7.87 (s, 1H), 7.82 (d, J = 7.8 Hz, 1H), 7.72 (s, 1H), 7.70 (s,1H), 7.58 (t, J = 7.7 Hz, 1H), 7.41 (t, J = 8.0 Hz, 1H), 7.28 (s, 1H), 6.62(d, J = 9.2 Hz, 1H), 6.51 (s, 1H), 3.88 (s, 4H), 3.77 (s, 3H), 3.14 (s, 4H), 2.01 (s, 1H), 1.07 (d, J= 8.7 Hz, 2H), 0.79 (d, J = 5.4 Hz, 2H). 13 C NMR (100MHz, CDCl3) δ 149.33, 147.84, 147.48, 147.32, 146.30, 141.11, 137.50, 133.70,129.62, 128.85, 128.67, 126.57, 126.49, 125.08, 123.12, 119.66, 108.04,100.19, 67.08, 55.90, 50.54, 15.57, 9.86. HRMS (ESI) calcd for C 28 H 28 N4O2[M +H] + , 453.2285; found, 453.2280. HPLC retention time = 5.115 min, purity = 97.17%, ( l = 254 nm).

[0160] Example 82 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-82. The preparation method of compound I-82 is basically the same as in Example 39, except that 5-methylthiophene-2-boronic acid is replaced with (4-(1-cyanocyclopropyl)phenyl)boronic acid. The yield of compound I-82 obtained is 47.6%. The structure of compound I-82 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.84 (d, J = 8.9 Hz, 1H), 7.90 (dd, J = 8.2, 1.6 Hz, 1H), 7.83-7.82 (m, 1H), 7.81 – 7.80 (m, 2H), 7.73(s, 1H), 7.62-7.57 (m, 1H), 7.52-7.51 (m, 1H), 7.50-7.49 (m, 1H), 7.44-7.40(m, 1H), 6.61 (dd, J = 8.9, 2.6 Hz, 1H), 6.50 (d, J= 2.6 Hz, 1H), 3.88 –3.77 (m, 4H), 3.77 (s, 3H), 3.14 – 3.12 (m, 4H), 1.84 – 1.81 (m, 2H), 1.51 –1.48 (m, 2H). 13 C NMR (100 MHz, CDCl3) δ 149.27, 147.46, 147.26, 146.76,141.27, 138.00, 137.40, 136.22, 130.04, 129.46, 128.89, 126.67, 126.59,125.32, 122.80, 122.33, 119.71, 107.93, 100.05, 67.06, 55.94, 50.47, 18.76,13.98. HRMS (ESI) calcd for C 29 H 27 N5O2[M + H] + , 478.2238; found, 478.2237. HPLC retention time = 4.595 min, purity = 97.00%, ( l = 254 nm).

[0161] Example 83 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-83. The preparation method of compound I-83 includes the following steps: oxalate dihydrate (2.78 g, 22.03 mmol) and choline chloride (3.08 g, 22.03 mmol) are stirred at 100 °C for 30 min to form a eutectic solvent. Then, 4,5-dimethyl-1,2-phenylenediamine (compound a38) (2 g, 14.68 mmol) is reacted at 130 °C for 4 h. After the reaction is complete, hot water (50 mL) is added to the reaction mixture, the solid is collected by filtration and recrystallized from ethanol to obtain intermediate a44. Intermediate a44 (1 g, 5.26 mmol) is suspended in 5 mL of anhydrous dichloroethane solution, followed by the addition of sulfoxide (0.72 mL, 10.52 mmol) and N,N-dimethylformamide (0.040 mL, 0.53 mmol). Under nitrogen protection, the reaction mixture was reacted at reflux temperature, and the reaction progress was monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature, the crude reaction mixture was washed with 3 × 40 mL of water, and the aqueous phase was extracted with 3 × 30 mL of ethyl acetate. The extracted organic phase was dried over anhydrous sodium sulfate, and then filtered to remove the drying agent. The filtered organic phases were combined, the solvent was removed by rotary evaporation, and the intermediate b50 was obtained by column chromatography. Intermediate b50 (1 g, 4.40 mmol), 2-methoxy-4-morpholinoaniline (1.83 g, 8.81 mmol), and... N,N -Diisopropylethylamine (1.15 mL, 6.61 mmol) dissolved in 5 mL N,N The reaction was carried out in dimethylformamide at 100 °C, and the reaction progress was monitored by thin-layer chromatography. After the reaction was completed, the mixture was cooled to room temperature, the crude reaction mixture was washed with 3 × 40 mL of water and the aqueous phase was extracted with 3 × 30 mL of ethyl acetate. The extracted organic phase was dried over anhydrous sodium sulfate and then filtered to remove the drying agent. The filtered organic phases were combined, the solvent was removed by rotary evaporation, and the intermediate b56 was obtained by column chromatography. Intermediate b56 (200 mg, 0.50 mmol), 4-(methanesulfonyl)phenylboronic acid (120 mg, 0.60 mmol), potassium carbonate (138 mg, 1 mmol), and tetra(triphenylphosphine)palladium (29 mg, 0.025 mmol) were dissolved in a mixed solution of tetrahydrofuran and water (V tetrahydrofuran:V water = 3:1, 8 mL), and reacted at 65 °C under nitrogen protection, with the reaction progress monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature, washed with 3 × 20 mL of water, and the aqueous phase was extracted with 3 × 20 mL of dichloromethane. The extracted organic phase was dried over anhydrous sodium sulfate and then filtered to remove the drying agent. The filtered organic phases were combined, the solvent was removed by rotary evaporation, and compound II-83 was obtained by column chromatography in 57.6% yield. The structure of compound II-83 was analyzed by nuclear magnetic resonance (NMR), and the structural characterization results are as follows:1 H NMR (400 MHz, CDCl3) δ 8.78 (d, J = 8.8 Hz, 1H), 8.17 (s, 1H), 8.15 (s, 1H), 8.06 (s, 1H), 8.04 (s, 1H), 7.66(s, 1H), 7.63 (s, 1H), 7.49 (s, 1H), 6.61 (dd, J = 8.9, 2.6 Hz, 1H), 6.51 (d, J = 2.6 Hz, 1H), 3.89-3.87 (m, 4H), 3.76 (s, 3H), 3.15 – 3.13 (m, 4H), 3.12(s, 3H), 2.46 (s, 3H), 2.42 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 149.18,147.42, 146.71, 144.07, 142.79, 141.39, 140.97, 140.06, 136.24, 135.54,130.07, 128.38, 128.34, 126.36, 122.77, 119.69, 107.90, 100.01, 67.07, 55.92,50.48, 44.69, 20.50, 20.06. HRMS (ESI) calcd for C 28 H 30 N4O4S[M + H] + , 519.2061;found, 519.2064. HPLC retention time = 4.503 min, purity = 94.39%, ( l = 254 nm).

[0162] Example 84 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-84. The preparation method of compound I-84 is basically the same as in Example 83, except that 4,5-dimethyl-1,2-phenylenediamine is replaced with 4,5-difluorophenyl-1,2-diamine. The yield of compound I-84 obtained is 63.2%. The structure of compound I-84 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.66 (d, J= 8.9 Hz, 1H), 8.20(s, 1H), 8.18 (s, 1H), 8.06 (s, 1H), 8.04 (s, 1H), 7.66 (dd, J = 10.5, 8.2Hz, 1H), 7.60 (s, 1H), 7.58 – 7.55 (m, 1H), 6.60 (dd, J = 8.9, 2.6 Hz, 1H), 6.50 (d, J = 2.5 Hz, 1H), 3.90 – 3.87 (m, 4H), 3.77 (s, 3H), 3.16 (d, J = 4.9Hz, 4H), 3.14 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 149.41, 148.01, 147.10,145.46, 141.96, 141.81, 138.94, 138.83, 133.84, 133.73, 129.94, HRMS (ESI) calcd for C 26 H 24 F2N4O4S[M + H] + , 527.1559;found, 527.1556. HPLC retention time = 4.466 min, purity = 99.26%, ( l = 254 nm).

[0163] Example 85 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-85. The preparation method of compound I-85 is basically the same as in Example 83, except that 4,5-dimethyl-1,2-phenylenediamine is replaced with 4,5-dichlorophenyl-1,2-diamine. The yield of compound I-85 obtained is 67.1%. The structure of compound I-85 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J= 9.0 Hz, 1H), 8.20(s, 1H), 8.18 (s, 1H), 8.06 (s, 1H), 8.04 (s, 1H), 8.00 (s, 1H), 7.95 (s,1H), 7.68 (s, 1H), 6.59 (d, J = 8.2 Hz, 1H), 6.50 (s, 1H), 3.90 – 3.87 (m,4H), 3.77 (s, 3H), 3.16 (d, J = 4.2 Hz (4H), 3.14 (s, 3H). 13 C NMR (101 MHz, CDCl3) δ 149.35, 147.76, 147.03, 145.40, 142.46, 141.78, 141.56, 137.43,130.66, 130.08, 129.05, 128.48, 126.85, 125.68, 122.43, 120.00, 107.90,99.95, 67.08, 55.98, 50.41, 44.69. HRMS (ESI) calcd for C 26 H 24 Cl2N4O4S[M + H] + ,559.0968; found, 559.0969. HPLC retention time = 4.493 min, purity = 96.59%, ( l = 254nm).

[0164] Example 86 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-86. The preparation method of compound I-86 is basically the same as in Example 83, except that 4,5-dimethyl-1,2-phenylenediamine is replaced with 4-chloro-1,2-phenylenediamine. The yield of compound I-86 obtained is 64.7%. The structure of compound I-86 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400MHz, CDCl3) δ 8.73 (d, J = 8.9Hz, 1H), 8.19 (s,1H), 8.17 (s, 1H), 8.06(s, 1H), 8.04 (s,1H),7.82 (d, J = 8.4 Hz, 2H),7.64(s,1H), 7.39 (d, J= 8.2 Hz, 1H), 6.60 (d, J = 8.0Hz,1H), 6.50(s, 1H), 3.88 (s,4H), 3.77 (s,3H), 3.16 (d, J = 4.8 Hz, 4H), 3.13 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ149.37, 147.99, 147.34, 147.01, 146.24,145.51,142.09,142.00,141.88,136.32,135.83,130.06,128.62,125.83,121.85,120.10,107.73,99.74,67.02, 55.92,50.22, 44.56. HRMS (ESI) calcd for C 26 H 25 ClN4O4S[M + H] + ,525.1358; found,525.1361. HPLC retention time = 4.497 min, purity = 97.33% ( l =254nm).

[0165] Example 87 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-87. The preparation method of compound I-87 is basically the same as in Example 83, except that 4,5-dimethyl-1,2-phenylenediamine is replaced with 4-methoxy-o-phenylenediamine. The yield of compound I-87 is 55.3%. The structure of compound I-87 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400 MHz, CDCl3) δ 8.76 (d, J = 8.8 Hz, 1H), 8.17 (s,1H), 8.15 (s, 1H), 8.07 (s, 1H), 8.05 (s, 1H), 7.79 (d, J = 8.9 Hz, 1H), 7.54(s, 1H), 7.18 (d, J = 2.8 Hz, 1H), 7.10 (dd, J = 9.2, 2.8 Hz, 1H), 6.63 (dd, J = 9.0, 2.6 Hz, 1H), 6.51 (d, J= 2.6 Hz, 1H), 3.97 (s, 3H), 3.90-3.87 (m,4H), 3.78 (s, 3H), 3.16-3.13 (m, 4H), 3.12 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ161.66, 149.37, 147.67, 147.32, 143.16, 142.69, 142.21, 141.33, 133.10,130.04, 129.98, 128.42, 122.43, 119.98, 117.90, 107.82, 105.55, 100.00,67.05, 55.93, 55.84, 50.41, 44.68. HRMS (ESI) calcd for C 27 H 328 N4O5S[M + H] + ,521.1853; found, 521.1857. HPLC retention time = 4.285 min, purity = 95.70%, ( l = 254nm).

[0166] Example 88 This embodiment provides a quinoxaline compound with general formula I, specifically compound I-88. The preparation method of compound I-88 is basically the same as in Example 83, except that 4,5-dimethyl-1,2-phenylenediamine is replaced with methyl 3,4-diaminobenzoate. The yield of compound I-88 is 50.9%. The structure of compound I-88 was analyzed using nuclear magnetic resonance (NMR) technology, and the structural characterization results are as follows: 1 H NMR (400MHz, CDCl3) δ 8.78 (d, J = 8.8 Hz, 1H), 8.62(d, J = 2.0 Hz, 1H), 8.24(dd, J = 8.8, 2.0 Hz, 1H), 8.21 (s, 1H), 8.19 (s,1H), 8.09 (s, 1H), 8.07 (s, 1H), 7.83 (d, J = 8.7Hz, 1H), 7.76 (s, 1H), 6.61(dd, J = 8.8, 2.7 Hz, 1H), 6.50 (d, J= 2.6 Hz, 1H), 3.97 (s, 3H), 3.90 –3.87 (m, 4H), 3.78 (s, 3H), 3.16 (d, J = 5.0 Hz, 4H), 3.15 (s, 3H). 13 C NMR(100 MHz, CDCl3) δ 166.79, 149.47, 148.19, 147.75, 146.55, 144.47, 142.02,141.81, 136.41, 131.61, 130.57, 129.98, 128.53, 126.87, 126.73, 121.58,120.41, 107.69, 99.62, 67.00, 55.97, 52.43, 50.14, 44.64. HRMS (ESI) calcdfor C 28 H 28 N4O6S [M + H] + , 549.1802; found, 549.1806. HPLC retention time = 4.246 min, purity = 96.58% ( l =254nm).

[0167] Experimental Example 1: Determination of LSD1 Inhibitory Activity For the LSD1 inhibitory activity assay, the test samples were quinoxaline compounds I-1 to I-88 purified in Examples 1-88. The sample stock solution was prepared as follows: 1-2 mg of sample was weighed and dissolved in DMSO to a concentration of 20 mM. The solution was stored at 4°C for later use, and diluted to the required concentration with DMSO before the experiment. After incubating the test sample with LSD1 protein at room temperature, the LSD1 substrate H3K4me2 was added and incubated again. Finally, the fluorescent dye Amplex and horseradish peroxidase HRP were added and incubated at room temperature. Fluorescence values ​​were detected on a microplate reader at excitation light of 530 nm and emission light of 590 nm. The inhibition rate was calculated using the following formula: The inhibition rate at various concentrations was calculated using SPSS software, and the IC50 was determined. 50 The values ​​are shown in Table 1. Among them, IC... 50 During the value test, only compounds with an inhibition rate greater than 50% at 10 μM were tested.

[0168] Table 1. LSD1 inhibitory activity and IC50 of the quinoxaline compounds in Examples 1-88 50 value

[0169] As shown in Table 1, the quinoxaline compounds I-1 to I-88 provided by this invention exhibit varying degrees of inhibitory activity against LSD1. Among them, compound I-57 has the highest IC50 value. 50 The effective concentration of the compound provided in this invention to exert LSD1 inhibitory activity is only 0.127 μM. This demonstrates that the effective concentration is low, which is beneficial for reducing drug dosage and improving efficacy, showing good potential for drug development targeting LSD1.

[0170] Experimental Example 2: Gastric Cancer Cell Inhibitory Activity Test The inhibitory activity of compound I-57 from Example 57 on the proliferation of HGC-27 gastric cancer cell line was tested using the CCK-8 assay. The assay method is as follows: HGC-27 cells were divided into groups of 2 × 10⁶ cells per well. 3 Cells were seeded at a density of 100 μL in 96-well cell culture plates, with a blank control group (containing only culture medium, no cells) included. Cells were cultured for 12 h to allow adherence. After cell adherence, the original culture medium was discarded, and 100 μL of culture medium containing different concentrations of the test compound (I-57) was added to each well. Six replicates were performed for each treatment, and cells were cultured for another 7 days. After culture, 10 μL of CCK-8 reagent was added to each well, gently vortexed to mix, and incubated for another 3 h in the dark. Finally, the absorbance of each well was measured at 450 nm using a microplate reader. GraphPad Prism 10.1.2 software was used for data processing and curve fitting to determine the IC50. 50 The inhibition rate (%) was calculated as follows: (OD blank group - OD experimental group) / (OD blank group - OD negative control group) × 100%. The results are shown in Table 2.

[0171] Table 2. Inhibitory activity of compound I-57 against gastric cancer cells.

[0172] As shown in Table 2, compound I-57 exhibits good inhibitory activity against gastric cancer cells, with an IC50 value of [missing information]. 50 It is only 6.941 μM.

[0173] In summary, the quinoxaline compounds provided by this invention have a novel skeleton, and experiments have confirmed that these compounds exhibit good inhibitory activity against LSD1 and human gastric cancer cells. Therefore, this invention can provide a molecular basis and data support for the development of drugs targeting LSD1 or anti-gastric cancer drugs, and can also provide potential lead compounds for the development of drugs targeting LSD1 and anti-gastric cancer drugs.

Claims

1. A quinoxaline compound, characterized in that, The compound represented by Formula I or a pharmaceutically acceptable salt thereof: ； In Formula I, X is selected from one of -, O, NH, NH-NH, NH-CH2, and N(CH3)-CH2; R1 is selected from One of them; R2 is selected from One of them; R3 is selected from one of H, 6,7-CH3, 6,7-F, 6,7-Cl, 6-Cl, 7-OCH3, and 7-COOCH3.

2. The quinoxaline compound according to claim 1, characterized in that, The quinoxaline compounds are selected from compounds with the following structures or pharmaceutically acceptable salts thereof: 。 3. An application of a quinoxaline compound as described in claim 1 or 2, characterized in that, The application is the use of quinoxaline compounds in the preparation of drugs that target and inhibit LSD1; or the application is the use of quinoxaline compounds in the preparation of antitumor drugs.

4. The application of the quinoxaline compounds according to claim 3, characterized in that, The antitumor drug mentioned is an anti-gastric cancer drug.

5. The application of the quinoxaline compounds according to claim 4, characterized in that, The aforementioned anti-gastric cancer drug is a drug that inhibits the activity of gastric cancer cells.

6. The application of the quinoxaline compounds according to claim 5, characterized in that, The gastric cancer cells were HGC-27 cells.

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