Preparation method and application of pyridine derivative compound

Abstract

The invention discloses a preparation method and application of a pyridine derivative, and belongs to the technical field of chemical synthesis, the structural formula of the pyridine derivative is shown as follows: in the # imgabs0 # formula, the R1 group is one of 4-CH3, 4-OCH3, 4-F, 4-Cl and 4-Br; the R2 is one of-C5H9 and-C6H11, and the R3 is one of-C6H9 and-C6H11; the R3 group is one of 3-F, 3-H and 3-CH3; the pyridine derivative prepared by the invention takes a pyridine ring as a structural center, has very important medicinal value, and has wide application in anti-tumor, anti-cancer, antibacterial and other biological medicines.

Description

Technical Field

[0001] The invention relates to a preparation method and application of a pyridine derivative, belonging to the technical field of chemical synthesis. Background Art

[0002] The pyridine core is a key component of artificial and naturally occurring bioactive compounds and is a component of several alkaloids. The presence of various functional groups on the ring, such as chlorine, methoxy, amino, hydroxyl, cyano, nitro, hydrazide, etc., increases the pharmacological activity. Among them, substituted pyridines have antihypertensive, antipyretic, anti-inflammatory and analgesic effects and can be used as cardiotonic agents, antibacterial agents, and also have anticancer activity. Therefore, it is of great value to explore the synthesis of pyridine derivatives. Earlier, Wang et al. reported in Synth. Commun. 2004, 34, 4331. that aromatic aldehydes, malononitrile and 4-amino-2,6-dihydroxypyrimidine were used as raw materials in KF / Al 2 O 3 The reaction was carried out for 5-8 hours in the presence of a catalyst to synthesize tetrahydropyrido[2,3-d]pyrimidine. Wu et al. reported an improvement on the Skraup synthesis method in Bioorg. Med. Chem. Lett. 2015, 25, 3251. 2 PhSO 3 Na replaced iodine as an oxidant to synthesize pyrido[3,2-b]pyridine at 150°C. At the same time, there are also photocatalytic expansions of pyridine synthesis, such as Rammal et al., in Org. Lett. 2020, 22, 19, 7671–7675, who published a study on the combination of N-alkoxypyridinium ions and alkanes under visible light and catalyst conditions. Due to the limitation of reaction specificity, only the combination of quaternary and higher cycloalkanes was achieved; it can be seen that the preparation method of traditional pyridine derivatives usually requires strong Lewis acids, strong bases, high temperatures or strong substrate design and specificity to achieve the derivatization of the pyridine core. Therefore, it is urgent to find a new method for constructing pyridine derivatives that is simple, efficient, and has mild reaction conditions. Summary of the invention

[0003] In view of the problems in the prior art, the object of the present invention is to provide a simple and efficient method for preparing pyridine derivatives.

[0004] The technical solution adopted by the present invention is as follows:

[0005] A method for preparing pyridine derivatives, characterized in that it comprises the following steps: using olefin, alkylboronic acid and cyanopyridine as raw materials, reacting in an organic solvent under the induction of visible light to prepare pyridine derivatives.

[0006] The olefin is any one of a styrene compound and vinylthiophene.

[0007] When the olefin is a styrene compound, the synthesized pyridine derivative has the following structural formula:

[0008]

[0009] Where:

[0010] The R 1 The group is CH 3 、OCH 3 , one of F, Cl, Br;

[0011] The R 2 The group is C 5 H 9 , C 6 H 11 One of;

[0012] The R 3 The group is F, H, CH 3 , one of Cl.

[0013] The reaction equation involved is as follows:

[0014]

[0015] When the olefin is vinylthiophene, the synthesized pyridine derivative has the following structural formula:

[0016]

[0017] Further settings are:

[0018] The molar ratio of the raw materials in the reaction is alkylboronic acid:olefin:cyanopyridine=1-3:1-3:1.

[0019] The organic solvent is one of acetone, dichloroethane (DCE), N,N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO).

[0020] The reaction is carried out in the presence of a catalyst, preferably [Ir(dtbbpy)(ppy) 2 ][PF 6 ]、4CzIPN、Ru(bpy) 3 (PF 6 ) 2 One of them.

[0021] The reaction is carried out in the presence of a base, preferably K 3 PO 4 、tBuOK、tBuONa、Cs 2 CO3 、NaHCO 3 , CH 3 One of COONa and DIPEA.

[0022] After the reaction is completed, the product is purified by using petroleum ether and ethyl acetate as developing agents, separating by column chromatography, desolventizing and concentrating, and then drying with anhydrous sodium sulfate.

[0023] Another object of the present invention is to provide a use of a pyridine derivative in the preparation of anti-tumor, anti-cancer or antibacterial drugs.

[0024] The pyridine derivatives prepared by the present invention have a pyridine ring as the structural center, have very important medicinal value, and have been widely used in anti-tumor, anti-cancer, antibacterial and other biomedicines.

[0025] It can be seen from the above description that the present invention has the following advantages:

[0026] 1. The present invention solves the difficulties of the existing process and provides a safe, green and easy-to-operate method for preparing pyridine, which uses visible light to mediate rapid derivatization.

[0027] 2. The present invention uses low-cost substrates olefins, alkylboronic acid, and cyanopyridine under visible light conditions to synthesize high value-added derivatives, which has the advantages of low cost, mild reaction conditions, short time, and easy handling.

[0028] 3. The present invention utilizes visible light at room temperature, and the reaction conditions are mild, thus avoiding the potential safety hazards caused by high-temperature reactions, making it easy to control the reaction, and at the same time, the reaction operation process and post-processing are simple.

[0029] 4. The pyridine derivatives prepared by the present invention have a wide range of uses in anti-tumor, anti-cancer, antibacterial and other biomedical applications. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 This is the H NMR spectrum of the product prepared in Example 1.

[0031] Figure 2 This is the carbon NMR spectrum of the product prepared in Example 1.

[0032] Figure 3 This is the H NMR spectrum of the product prepared in Example 2.

[0033] Figure 4 This is the NMR carbon spectrum of the product prepared in Example 2.

[0034] Figure 5 This is the H NMR spectrum of the product prepared in Example 3.

[0035] Figure 6 This is the NMR carbon spectrum of the product prepared in Example 3.

[0036] Figure 7 This is the NMR fluorine spectrum of the product prepared in Example 3.

[0037] Figure 8 This is the H NMR spectrum of the product prepared in Example 4.

[0038] Fig. 9 This is the NMR carbon spectrum of the product prepared in Example 4.

[0039] Fig.10 This is the H NMR spectrum of the product prepared in Example 5.

[0040] Fig.11 This is the carbon NMR spectrum of the product prepared in Example 5.

[0041] Fig.12 This is the NMR fluorine spectrum of the product prepared in Example 5.

[0042] Fig.13 This is the H NMR spectrum of the product prepared in Example 6.

[0043] Fig.14 This is the carbon NMR spectrum of the product prepared in Example 6.

[0044] Fig.15 This is the H NMR spectrum of the product prepared in Example 7.

[0045] Fig.16 This is the NMR carbon spectrum of the product prepared in Example 7.

[0046] Fig.17 This is the H NMR spectrum of the product prepared in Example 8.

[0047] Fig.18 This is the NMR carbon spectrum of the product prepared in Example 8.

[0048] Fig.19 This is the H NMR spectrum of the product prepared in Example 9.

[0049] Fig. 20 This is the carbon NMR spectrum of the product prepared in Example 9.

[0050] Fig.21 This is the H NMR spectrum of the product prepared in Example 10.

[0051] Fig. 22 This is the carbon NMR spectrum of the product prepared in Example 10.

[0052] Fig.23 The figure shows the survival of Staphylococcus aureus in the blank control example of Example 1 (without adding the antibacterial sample of Example 1).

[0053] Fig.24 The figure shows the survival of Staphylococcus aureus after adding the antibacterial sample (10 mg / mL) in Example 1.

[0054] Fig.25 The figure shows the survival of Staphylococcus aureus in the blank control example of Example 3 (the antibacterial sample of Example 3 was not added).

[0055] Fig.26 This is the survival status of Staphylococcus aureus after adding the antibacterial sample (10 mg / mL) in Example 3.

[0056] Fig. 27 The figure shows the survival of Staphylococcus aureus in the blank control example of Example 5 (the antibacterial sample of Example 5 was not added).

[0057] Fig.28 This is the survival status of Staphylococcus aureus after adding the antibacterial sample (10 mg / mL) in Example 5. DETAILED DESCRIPTION

[0058] Combination Figure 1 to Figure 22 , describes in detail the specific embodiments of the present invention, but does not limit the claims of the present invention.

[0059] Example 1

[0060] Acetone (2.0 mL) was added to a 4 mL clear glass bottle with a magnetic stirring bar and a rubber stopper, and then 4-cyanopyridine (0.2 mmol, 0.0208 g) and [Ir(dtbbpy)(ppy) 2 ][PF 6 ](5.0mol%, 9.6mg) and 4-methylstyrene (0.6mmol, 0.0708g), K 3 PO 4 (0.2mmol, 0.0212g), cyclopentylboronic acid (0.4mmol, 0.0452g). The reaction mixture was reacted at ambient temperature under 3W blue LED (420nm) for 24 hours. After the reaction (monitored by TLC), the solid was centrifuged and the organic layer was concentrated. The crude mixture was washed with silica gel (eluted with EA:PE=1:10), dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified to obtain the desired product.

[0061] The reaction equations involved are as follows:

[0062]

[0063] Product characterization:

[0064] like Figure 1 As shown: 1H NMR(400MHz,Chloroform-d)δ8.46(d,J=6.2Hz,2H),7.15(d,J=6.1Hz,2H),7.10(s,4H),3.89(t,J=7.9Hz, 1H),2.30(s,3H),2.10–1.96(m,2H),1.79–1.69(m,2H),1.65–1.55(m,3H),1.49–1.41(m,2H),1.13(m,2H).

[0065] like Figure 2 As shown: 13 C NMR (101 MHz, CDCl 3 )δ154.24,149.26,139.94,135.77,128.90,127.31,122.80,48.95,41.16,37.22,32.13,24.67,20.56.

[0066] Replacement Example 2-14: Screening of Synthesis Conditions for Pyridine Derivatives

[0067] The preparation method is the same as that of Example 1, except that the type of reaction catalyst, organic solvent, base and reaction material ratio (cyclopentylboronic acid: 4-methylstyrene: 4-cyanopyridine) are adjusted, and their effects on the reaction are tested respectively.

[0068] Table 1

[0069]

[0070] As shown in Table 1, in the synthesis process of pyridine derivatives, when the reaction time is 24 h, K is added to the reaction system. 3 PO 4 And [Ir(dtbbpy)(ppy) 2 ][PF 6 ] as the catalyst and acetone as the solvent, the yield of the product obtained was the highest, with a yield of 73%.

[0071] Example 2

[0072] The preparation method is the same as that of Example 1, except that 4-methoxystyrene (0.6 mmol) is used instead of 4-methylstyrene (0.6 mmol). The yield of the obtained pure product 4-(2-cyclopentyl-1-(4-methoxyphenyl)ethyl)pyridine is 88%.

[0073] The reaction equations involved are as follows:

[0074]

[0075] Product characterization:

[0076] like Figure 3 As shown: 1 H NMR(400MHz,Chloroform-d)δ8.46(d,J=6.1Hz,2H),7.14(dd,J=7.3,4.6Hz,4H),6.84(d,J=8.7Hz,2H),3.89(d ,J=7.9Hz,1H),3.77(s,3H),2.09–1.94(m,2H),1.79–1.68(m,2H),1.64–1.55(m,3H),1.45(m,2H),1.14(m,2H).

[0077] like Figure 4 As shown: 13 C NMR (101 MHz, CDCl 3 )δ158.30,154.87,149.70,135.48,128.85,123.22,114.05,55.26,48.97,41.75,37.69,32.79,32.59,25.16,25.14.

[0078] Example 3

[0079] The preparation method is the same as that of Example 1, except that 4-fluorostyrene (0.6 mmol) is used instead of 4-methylstyrene (0.6 mmol). The yield of the obtained pure product 4-(2-cyclopentyl-1-(4-fluorophenyl)ethyl)pyridine is 85%.

[0080] The reaction equations involved are as follows:

[0081]

[0082] Product characterization:

[0083] like Figure 5 As shown: 1 H NMR(400MHz,Chloroform-d)δ8.49–8.48(m,2H),7.17(dd,J=8.6,5.4Hz,2H),7.15–7.12(m,2H),6.98(t,J=8.7Hz,2H),3.91( t,J=7.9Hz,1H),2.02(td,J=7.5,1.9Hz,2H),1.79–1.69(m,2H),1.65–1.55(m,3H),1.46(tt,J=6.6,2.6Hz,2H),1.14(m,2H).

[0084] like Figure 6 As shown: 13C NMR (101 MHz, CDCl 3 )δ162.82,160.38,154.15,149.87,139.13,139.10,129.36,129.29,12 3.17,115.59,115.38,49.03,41.70,37.64,32.75,32.59,25.14,25.12.

[0085] like Figure 7 As shown: 19 F NMR (376MHz, Chloroform-d) δ-116.79.

[0086] Example 4

[0087] The preparation method is the same as that of Example 1, except that cyclohexylboronic acid (0.4 mmol) is used instead of cyclopentylboronic acid (0.4 mmol). The yield of the pure product 4-(2-cyclohexyl-1-(p-tolyl)ethyl)pyridine is 76%.

[0088] The reaction equations involved are as follows:

[0089]

[0090] Product characterization:

[0091] like Figure 8 As shown: 1 H NMR(400MHz,Chloroform-d)δ8.47–8.45(m,2H),7.25–7.13(m,2H),7.09(s,4H),3.99(t,J=7.9Hz,1H),2. 30(s,3H),1.92–1.85(m,2H),1.79–1.69(m,2H),1.68–1.55(m,3H),1.18–1.07(m,4H),0.99–0.87(m,2H).

[0092] like Fig. 9 As shown: 13 C NMR (101 MHz, CDCl 3 )δ154.82,149.73,140.44,136.20,129.39,127.78,123.30,47.17,42.91,34.88,33.51,33.27,26.59,26.14,26.11,21.04.

[0093] Example 5

[0094] The preparation method is the same as that of Example 1, except that 4-cyanopyridine (0.2 mmol) is replaced by 4-cyano-3-fluoropyridine (0.2 mmol), and the yield of the pure product 4-(2-cyclopentyl-1-(p-tolyl)ethyl)-3-fluoropyridine is 82%.

[0095] The reaction equations involved are as follows:

[0096]

[0097] Product characterization:

[0098] like Fig.10 As shown: 1 H NMR(400MHz,Chloroform-d)δ8.33(d,J=1.9Hz,1H),8.30(d,J=5.0Hz,1H),7.20(t,J=5.6Hz,1H),7.15(d,J=7.9Hz,2H),7.11 (d,J=7.9Hz,2H),4.29(t,J=7.9Hz,1H),2.31(s,3H),2.03(m,2H),1.80–1.72(m,2H),1.64–1.57(m,3H),1.47(m,2H),1.15(m 2H).

[0099] like Fig.11 As shown: 13 C NMR (101 MHz, CDCl 3 )δ159.18,156.65,145.78,145.73,141.34,141.22,139.14,138.15,137.89,136.48,129.4 0,129.16,127.86,125.96,123.07,41.87,40.74,37.79,32.79,32.51,25.14,25.11,21.04.

[0100] like Fig.12 As shown: 19 F NMR(376MHz,Chloroform-d)δ-133.01.

[0101] Example 6

[0102] The preparation method is the same as that of Example 1, except that 4-chlorostyrene (0.6 mmol) is used instead of 4-methylstyrene (0.6 mmol) to obtain pure product 4-(1-(4-chlorophenyl)-2-cyclopentylethyl)pyridine with a yield of 79%.

[0103] The reaction equations involved are as follows:

[0104]

[0105] Product characterization:

[0106] like Fig.13 As shown: 1 H NMR (400MHz, chloroform-d) δ8.53 (d, J=5.1Hz, 2H), 7.31 (d, J=8.3Hz, 2H), 7.18 (dd, J=7.0, 5.0Hz, 4H), 3.94 (t, J=7.9Hz, 1H), 2.06 (td, J=7.4,3.5 Hz, 2H), 1.77 (dddd, J=13.7, 10.5, 6.6, 2.6Hz, 2H), 1.64 (td, J=8.2, 4.0Hz, 3H), 1.50 (dp, J=7.5, 3.6Hz, 2H), 1.17 (dq, J=12.0, 7.9Hz, 2H).

[0107] like Fig.14 As shown: 13 C NMR (101MHz, CDCl3) δ153.92, 149.83, 141.87, 132.49, 129.28, 128.84, 123.20, 49.19, 41.50, 37.63, 32.77, 32.63, 25.12.

[0108] Example 7

[0109] The preparation method is the same as that of Example 1, except that 4-bromostyrene (0.6 mmol) is used instead of 4-methylstyrene (0.6 mmol) to obtain pure product 4-(1-(4-bromophenyl)-2-cyclopentylethyl)pyridine with a yield of 87%.

[0110] The reaction equations involved are as follows:

[0111]

[0112] Product characterization:

[0113] like Fig.15 As shown: 1 H NMR(400MHz,Chloroform-d)δ8.48(d,J=5.6Hz,2H),7.44–7.40(m,2H),7.14–7.11(m,2H),7.11– 7.07(m,2H),3.89(t,J=7.9Hz,1H),2.02(dt,J=7.4,3.5Hz,2H),1.74(m,2H),1.60(m,3H),1.46(m 2H),1.17–1.09(m,2H).

[0114] like Fig.16 As shown: 13 C NMR (101MHz, CDCl3) δ153.72,149.89,142.42,131.78,129.67,123.12,120.53,49.25,41.43,37.61,32.78,32.56,25.12.

[0115] Example 8

[0116] The preparation method is the same as that of Example 1, except that 2-vinylthiophene (0.6 mmol) is used instead of 4-methylstyrene (0.6 mmol) to obtain pure product 4-(2-cyclopentyl-1-(thiophen-2-yl)ethyl)pyridine with a yield of 71%.

[0117] The reaction equations involved are as follows:

[0118]

[0119] Product characterization:

[0120] like Fig.17 As shown: 1 H NMR(400MHz,Chloroform-d)δ8.50(d,J=4.7Hz,2H),7.19(d,J=4.7Hz,2H),7.16(d,J=5.4Hz,1H),6.93(dd,J=5.2,3.7Hz,1H ),6.84(d,J=3.5Hz,1H),4.16(t,J=7.8Hz,1H),2.12–2.02(m,2H),1.79–1.70(m,2H),1.60(m,3H),1.46(m,2H),1.14(m,2H).

[0121] like Fig.18 As shown: 13 C NMR (101MHz, CDCl3) δ153.85,149.87,147.38,126.76,124.31,123.96,123.06,45.39,43.41,37.72,32.72,32.42,25.16,25.12.

[0122] Example 9

[0123] The preparation method is the same as that of Example 1, except that 3-chloro-4-cyanopyridine (0.2 mmol) is used instead of 4-cyanopyridine (0.2 mmol) to obtain pure product 3-chloro-4-(2-cyclopentyl-1-(p-tolyl)ethyl)pyridine with a yield of 83%.

[0124] The reaction equations involved are as follows:

[0125]

[0126] Product characterization:

[0127] like Fig.19 As shown: 1 H NMR(400MHz,Chloroform-d)δ8.50(s,1H),8.37(d,J=5.1Hz,1H),7.21(d,J=5.1Hz,1H),7.15(d,J=8.2Hz,2H),7.11(d,J=8.1H z,2H),4.45(t,J=7.8Hz,1H),2.31(s,3H),2.08–1.92(m,2H),1.76(m,3H),1.62–1.57(m,2H),1.50–1.42(m,2H),1.17(m,2H).

[0128] like Fig. 20 As shown: 13 C NMR (101MHz, CDCl3) δ151.74,149.61,147.80,138.80,136.47,129.36,128.11,123.14,45.16,41.16,37.77,32.98,32.40,25.14,25.12,21.06.

[0129] Example 10

[0130] The preparation method is the same as that of Example 1, except that 2,6-dimethyl-4-cyanopyridine (0.2 mmol) is used instead of 4-cyanopyridine (0.2 mmol) to obtain pure product 4-(2-cyclopentyl-1-(p-tolyl)ethyl)-2,6-dimethylpyridine with a yield of 80%.

[0131] The reaction equations involved are as follows:

[0132]

[0133] Product characterization:

[0134] like Fig.21 As shown: 1H NMR(400MHz,Chloroform-d)δ7.10(s,4H),6.82(s,2H),3.80(t,J=7.9Hz,1H),2.46(s,6H) ,2.30(s,3H),2.07–1.92(m,2H),1.73(m,2H),1.64–1.54(m,3H),1.45(m,2H),1.13(m,2H).

[0135] like Fig. 22 As shown: 13 C NMR (101MHz, CDCl3) δ157.60,155.19,140.81,136.06,129.30,127.75,119.80,49.39,41.65,37.70,32.80,32.61,25.16,24.49,21.05.

[0136] Application Example: Antibacterial Performance Evaluation

[0137] The products prepared in Examples 1, 3 and 5 were evaluated for their antibacterial properties by the following methods:

[0138] 1. Preparation of antibacterial material samples

[0139] Accurately weigh an appropriate amount of each sample and serially dilute it to 1 mg / ml, 5 mg / mL, and 10 mg / mL, and test its inhibitory effect on Staphylococcus aureus.

[0140] 2. Preparation of Bacterial Suspension

[0141] Take each test strain, inoculate fresh slant medium, incubate at 35℃ for 16-20 hours, wash the bacterial moss with nutrient broth medium, compare turbidity with 0.5 McFarland turbidimeter tube, and dilute appropriately to a concentration of about 10 8 CFU / mL, serial dilution to 1~5×10 8 CFU / mL, 1~5×10 4 CFU / mL is reserved.

[0142] 3. Determination of antibacterial rate

[0143] 3.1 Inoculation

[0144] After turning on the clean bench fan for 30 minutes, perform sterile operation. Pipette 4.5 ml (1-5×10 5 CFU / mL) were added into sterile test tubes, and 0.5 mL of dilutions of antibacterial materials with concentrations of 1 mg / mL, 5 mg / mL, and 10 mg / mL were added respectively, and the numbers were counted after 4 hours.

[0145] 3.2 Colony count

[0146] Use a pipette to take 1 mL of the bacterial solution to be counted, place it in 9 mL of LB liquid culture medium, mix thoroughly, then use a new pipette to take 1 mL and add it to another 9 mL of LB liquid culture medium and mix thoroughly. Use the same method to make 10-fold serial dilutions.

[0147] 3.3 Counting culture

[0148] Aseptically operate, take 1mL of each dilution level bacterial solution and add it to a sterile plate, take the nutrient agar medium that has been melted and kept at a constant temperature of 46-48℃, add 15-20mL to each plate, mix thoroughly, cover and wait for solidification, and after solidification, invert the plate and culture it in a constant temperature incubator at 35±1℃ (Candida albicans and Aspergillus niger are cultured at 28±1℃) for 48 hours. After cultivation, count the number of bacteria in each dilution level plate.

[0149] 4. Counting rules

[0150] Select the dilution plate with the average colony count within the range (bacteria: between 30 and 300, fungi between 30 and 100) for counting. If all are less than 30, select the lowest dilution result for counting. The counting result multiplied by the corresponding dilution level is the final bacterial content of the test solution.

[0151] Calculation of viable bacteria count in sample solution: N = (C × D)

[0152] Where N: number of viable bacteria;

[0153] C: colony count; (the number of colonies grown in the plate)

[0154] D: dilution factor.

[0155] Calculation of the antibacterial rate: Antibacterial rate = (initial bacterial solution quantity - number of live bacteria in the sample solution) / initial bacterial solution quantity.

[0156] Table 2

[0157]

[0158] Table 3

[0159]

[0161] Table 4

[0162]

[0163] analyze:

[0164] Combined with Table 2-4 and Figure 23-28As shown: the products of different concentrations have a certain antibacterial effect on Staphylococcus aureus, among which 10 mg / mL is the best. The antibacterial rates of the products prepared in Examples 1, 3 and 5 are 96%, 100% and 97% respectively.

[0165] Summarize:

[0166] The present invention uses olefin as a bridging unit and realizes a three-component pyridine derivatization reaction with a cyanopyridine core as the core and an alkyl boric acid under the action of a base through visible light induction. The reaction conditions are mild, the raw materials are cheap and easily available, the operation process is simple, the reaction has wide universality, and the synthesis of traditional complex pyridine derivatives can be effectively replaced without complex substrate design. At the same time, since the compounds with pyridine as the core have high pharmacological activity, they have been widely used in anti-tumor, anti-cancer, antibacterial and other biomedicines.

[0167] It is understood that the above specific description of the present invention is only used to illustrate the present invention and is not limited to the technical solutions described in the embodiments of the present invention. Those skilled in the art should understand that the present invention can still be modified or replaced by equivalents to achieve the same technical effects; as long as the use requirements are met, they are within the protection scope of the present invention.

Claims

1. A pyridine derivative, the structural formula of which is as follows: Where: The R1 group is one of CH3, OCH3, F, Cl, and Br; The R2 group is C5H9, C6H 11 One of; The R3 group is one of F, H, CH3, and Cl.

2. A pyridine derivative, the structural formula of which is as follows:

3. A method for preparing a pyridine derivative, characterized in that: The method comprises the following steps: using olefin, alkylboronic acid and cyanopyridine as raw materials, reacting in an organic solvent under the induction of visible light to prepare pyridine derivatives.

4. The method for preparing a pyridine derivative according to claim 3, characterized in that: The molar ratio of the raw materials in the reaction is alkylboronic acid:olefin:cyanopyridine=1-3:1-3:

1.

5. The method for preparing a pyridine derivative according to claim 3, characterized in that: The olefin is any one of a styrene compound and vinylthiophene.

6. The method for preparing a pyridine derivative according to claim 3, characterized in that: The organic solvent is one of acetone, ethylene dichloride, N,N-dimethylformamide and dimethyl sulfoxide.

7. The method for preparing a pyridine derivative according to claim 3, characterized in that: The reaction is carried out in the presence of a catalyst, and the catalyst is one of [Ir(dtbbpy)(ppy)2][PF6], 4CzIPN, and Ru(bpy)3(PF6)2.

8. The method for preparing a pyridine derivative according to claim 3, characterized in that: The reaction is carried out in the presence of a base, and the base is one of K3PO4, tBuOK, tBuONa, Cs2CO3, NaHCO3, CH3COONa, and DIPEA.

9. The method for preparing a pyridine derivative according to claim 3, characterized in that: After the reaction is completed, the product is purified by using petroleum ether and ethyl acetate as developing agents, separating by column chromatography, desolventizing and concentrating, and then drying with anhydrous sodium sulfate.

10. Use of the pyridine derivatives according to claim 1 or 2 in the preparation of anti-tumor, anti-cancer or antibacterial drugs.

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