Preparation method and application of pyridine derivative compound

Abstract

The application discloses a preparation method and application of a pyridine derivative compound, belongs to the technical field of chemical synthesis, and has the structural formula as shown in the following formula: wherein the R1 group is one of 4-CH3, 4-OCH3, 4-F, 4-Cl and 4-Br; the R2 group is one of -C5H9 and -C6H 11 ; and the R3 group is one of 3-F, 3-H and 3-CH3. The pyridine derivative compound prepared by the application has a pyridine ring as a structural center and has very important medicinal value and is widely applied in the fields of antitumor, anticancer, antibacterial and other biological medicines.

Description

Technical Field

[0001] This invention relates to a method for preparing pyridine-derived compounds and their applications, belonging to the field of chemical synthesis technology. Background Technology

[0002] Pyridine is a key component in both artificially and naturally occurring bioactive compounds and is a constituent of several alkaloids. The presence of various functional groups on its ring, such as chlorine, methoxy, amino, hydroxyl, cyano, nitro, and hydrazide, increases its pharmacological activity. Substituted pyridines possess antihypertensive, antipyretic, anti-inflammatory, and analgesic effects, and can be used as cardiotonic agents, antibacterial agents, and also exhibit anticancer activity. Therefore, exploring the synthesis of pyridine-derived compounds is of great value. Early on, Wang et al. reported in Synth. Commun. 2004, 34, 4331, the synthesis of tetrahydropyridine[2,3-d]pyrimidine from aromatic aldehydes, malononitriles, and 4-amino-2,6-dihydroxypyrimidine in the presence of a KF / Al2O3 catalyst for 5-8 h. Wu et al. reported an improvement to the Skraup synthesis method in Bioorg. Med. Chem. Lett. 2015, 25, 3251, namely, using m-NO2PhSO3Na instead of iodine as the oxidant to synthesize pyridino[3,2-b]pyridine at 150℃. Meanwhile, there are also extensions to the synthesis of pyridine using photocatalysis. For example, Rammal et al. published in Org. Lett. 2020, 22, 19, 7671–7675, on the combination of N-alkoxypyridine ions with alkanes under visible light and catalytic conditions. However, due to the limited reaction specificity, only the combination of four-membered and higher cycloalkanes was achieved. It is evident that the preparation methods of traditional pyridine derivatives usually require strong Lewis acids, strong bases, high temperatures, or very strong substrate designability and specificity to achieve the derivatization of the pyridine core. Therefore, there is an urgent need to find a new scheme 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 purpose of this invention is to provide a simple and efficient method for preparing pyridine derivatives.

[0004] The technical solution adopted in this invention is as follows:

[0005] A method for preparing a pyridine derivative compound, characterized by comprising the following steps: using olefins, alkylboronic acid, and cyanopyridine as raw materials, reacting them in an organic solvent under visible light induction to prepare the pyridine derivative compound.

[0006] The olefin is any one of styrene compounds or vinylthiophene.

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

[0008]

[0009] In the formula:

[0010] The R1 group is one of CH3, OCH3, F, Cl, and Br;

[0011] The R2 group is C5H9 or C6H. 11 One of them;

[0012] The R3 group is one of F, H, CH3, and Cl.

[0013] The reaction equations involved are as follows:

[0014]

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

[0016]

[0017] Further settings include:

[0018] The molar ratio of the reactants 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 one of [Ir(dtbbpy)(ppy)2][PF6], 4CzIPN, or Ru(bpy)3(PF6)2.

[0021] The reaction is carried out in the presence of a base, preferably one of K3PO4, tBuOK, tBuONa, Cs2CO3, NaHCO3, CH3COONa, or DIPEA.

[0022] After the reaction is completed, the product is purified by column chromatography using petroleum ether and ethyl acetate as the developing solvent. After solvent removal and concentration, the product is dried with anhydrous sodium sulfate.

[0023] Another objective of this invention is to provide the use of pyridine derivatives in the preparation of antitumor, anticancer, or antibacterial drugs.

[0024] The pyridine derivatives prepared in this invention, with the pyridine ring as the structural center, have very important medicinal value and have been widely used in biomedicine such as antitumor, anticancer, and antibacterial applications.

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

[0026] 1. This invention solves the difficulties of existing processes and provides a safe, green, and simple method for preparing pyridine, which utilizes visible light to achieve rapid derivatization.

[0027] 2. This invention enables the synthesis of high-value-added derivatives using low-cost substrates such as olefins, alkylboronic acids, and cyanopyridine under visible light conditions. It has the advantages of low cost, mild reaction conditions, short reaction time, and easy processing.

[0028] 3. This invention utilizes visible light at room temperature, resulting in mild reaction conditions that avoid the safety hazards associated with high-temperature reactions. The reaction is easy to control, and the reaction operation and post-processing are simple.

[0029] 4. The pyridine derivatives prepared by this invention have wide applications in biomedicine, including antitumor, anticancer, and antibacterial applications. Attached Figure Description

[0030] Figure 1 The image shows the hydrogen NMR spectrum of the product prepared in Example 1.

[0031] Figure 2 The image shows the carbon NMR spectrum of the product prepared in Example 1.

[0032] Figure 3 The image shows the 1H NMR spectrum of the product prepared in Example 2.

[0033] Figure 4 The image shows the carbon NMR spectrum of the product prepared in Example 2.

[0034] Figure 5 The image shows the 1H NMR spectrum of the product prepared in Example 3.

[0035] Figure 6 The image shows the carbon NMR spectrum of the product prepared in Example 3.

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

[0037] Figure 8 The image shows the 1H NMR spectrum of the product prepared in Example 4.

[0038] Figure 9 The image shows the carbon NMR spectrum of the product prepared in Example 4.

[0039] Figure 10The image shows the 1H NMR spectrum of the product prepared in Example 5.

[0040] Figure 11 The image shows the carbon NMR spectrum of the product prepared in Example 5.

[0041] Figure 12 The NMR fluorine spectrum of the product prepared in Example 5 is shown.

[0042] Figure 13 The image shows the 1H NMR spectrum of the product prepared in Example 6.

[0043] Figure 14 The image shows the carbon NMR spectrum of the product prepared in Example 6.

[0044] Figure 15 The image shows the 1H NMR spectrum of the product prepared in Example 7.

[0045] Figure 16 The image shows the carbon NMR spectrum of the product prepared in Example 7.

[0046] Figure 17 The image shows the 1H NMR spectrum of the product prepared in Example 8.

[0047] Figure 18 The image shows the carbon NMR spectrum of the product prepared in Example 8.

[0048] Figure 19 The image shows the 1H NMR spectrum of the product prepared in Example 9.

[0049] Figure 20 The image shows the carbon NMR spectrum of the product prepared in Example 9.

[0050] Figure 21 The image shows the 1H NMR spectrum of the product prepared in Example 10.

[0051] Figure 22 The image shows the carbon NMR spectrum of the product prepared in Example 10.

[0052] Figure 23 The survival status of Staphylococcus aureus in the blank control example of Example 1 (without the addition of the antibacterial sample of Example 1).

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

[0054] Figure 25 The survival status of Staphylococcus aureus in the blank control example of Example 3 (without the antibacterial sample of Example 3).

[0055] Figure 26 The survival of Staphylococcus aureus after adding antibacterial sample (10 mg / mL) in Example 3.

[0056] Figure 27 The survival status of Staphylococcus aureus in the blank control example of Example 5 (without the antibacterial sample of Example 5).

[0057] Figure 28 The survival of Staphylococcus aureus after adding antibacterial sample (10 mg / mL) in Example 5. Detailed Implementation

[0058] Combination Figures 1 to 22 This invention provides a detailed description of specific embodiments of the invention, but does not limit the scope of the claims.

[0059] Example 1

[0060] Acetone (2.0 mL) was added to a 4 mL clear glass bottle equipped with a magnetic stir bar and a rubber stopper. Then, 4-cyanopyridine (0.2 mmol, 0.0208 g), [Ir(dtbbpy)(ppy)2][PF6] (5.0 mol%, 9.6 mg), 4-methylstyrene (0.6 mmol, 0.0708 g), K3PO4 (0.2 mmol, 0.0212 g), and cyclopentylboronic acid (0.4 mmol, 0.0452 g) were added to the bottle. The reaction mixture was reacted at ambient temperature under a 3 W blue LED (420 nm) for 24 hours. After the reaction (monitored by TLC), the solid was centrifuged, and the organic layer was concentrated. The crude mixture was dried over silica gel (eluted with EA:PE = 1:10), 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: 1 H 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: 13C NMR (101MHz, CDCl3) 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] Alternative Example 2-14: Screening of Synthetic Conditions for Pyridine Derivatives

[0067] The preparation method is the same as in Example 1, except that the types of reaction catalysts, organic solvents, bases, and reactant ratios (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 of pyridine derivatives, the highest yield of the product (73%) was obtained when the reaction time was 24 h, K3PO4 was added to the reaction system, [Ir(dtbbpy)(ppy)2][PF6] was used as the catalyst, and acetone was used as the solvent.

[0071] Example 2

[0072] The preparation method is the same as in Example 1, except that 4-methoxystyrene (0.6 mmol) is used instead of 4-methylstyrene (0.6 mmol) to obtain the pure product 4-(2-cyclopentyl-1-(4-methoxyphenyl)ethyl)pyridine with a yield of 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: 13C NMR (101MHz, CDCl3) 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 in Example 1, except that 4-fluorostyrene (0.6 mmol) is used instead of 4-methylstyrene (0.6 mmol) to obtain pure product 4-(2-cyclopentyl-1-(4-fluorophenyl)ethyl)pyridine with a yield of 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: 13 C NMR (101MHz, CDCl3) δ162.82,160.38,154.15,149.87,139.13,139.10,129.36,1 29.29,123.17,115.59,115.38,49.03,41.70,37.64,32.75,32.59,25.14,25.12.

[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 in Example 1, except that cyclohexylboronic acid (0.4 mmol) is used instead of cyclopentylboronic acid (0.4 mmol) to obtain pure product 4-(2-cyclohexyl-1-(p-tolyl)ethyl)pyridine with a yield of 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 Figure 9 As shown: 13 C NMR (101MHz, CDCl3) 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 in Example 1, except that 4-cyano-3-fluoropyridine (0.2 mmol) is used instead of 4-cyanopyridine (0.2 mmol) to obtain the pure product 4-(2-cyclopentyl-1-(p-tolyl)ethyl)-3-fluoropyridine with a yield of 82%.

[0095] The reaction equations involved are as follows:

[0096]

[0097] Product characterization:

[0098] like Figure 10 As shown: 1H 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 Figure 11 As shown: 13 C NMR (101MHz, CDCl3) δ159.18,156.65,145.78,145.73,141.34,141.22,139.14,138.15,137.89,136. 48,129.40,129.16,127.86,125.96,123.07,41.87,40.74,37.79,32.79,32.51,25.14,25.11,21.04.

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

[0101] Example 6

[0102] The preparation method is the same as in 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 Figure 13 As shown: 1H NMR (400MHz, chloroform-d) δ 8.53 (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 Figure 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 in 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 Figure 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 Figure 16 As shown: 13C 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 was the same as in Example 1, except that 2-vinylthiophene (0.6 mmol) was used instead of 4-methylstyrene (0.6 mmol) to obtain the 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 Figure 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 Figure 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 was the same as in Example 1, except that 3-chloro-4-cyanopyridine (0.2 mmol) was 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 Figure 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 Figure 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 in Example 1, except that 2,6-dimethyl-4-cyanopyridine (0.2 mmol) is used instead of 4-cyanopyridine (0.2 mmol) to obtain the pure product 4-(2-cyclopentyl-1-(p-tolyl)ethyl)-2,6-dimethylpyridine in 80% yield.

[0131] The reaction equations involved are as follows:

[0132]

[0133] Product characterization:

[0134] like Figure 21 As shown: 1 H 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 Figure 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: Evaluation of Antibacterial Performance

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

[0138] 1. Sample preparation for testing antibacterial materials

[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 with fresh slant agar, and incubate at 35°C for 16–20 hours. Wash off the bacterial growth with an appropriate amount of nutrient broth, compare the turbidity with a 0.5 McFarland turbidimetric tube, and dilute appropriately to a concentration of approximately 10. 8 CFU / mL, serially diluted to 1–5 × 10⁻⁵ 8 CFU / mL, 1~5×10 4 CFU / mL available for use.

[0142] 3. Antibacterial rate determination

[0143] 3.1 Vaccination

[0144] After turning on the ultra-clean hood fan for 30 minutes, perform aseptic procedures. Aspirate 4.5 ml (1–5 × 10⁻⁵) of each test bacterial solution. 5 Add CFU / mL to a sterile test tube, and then add 0.5 mL of antibacterial material dilution at concentrations of 1 mg / mL, 5 mg / mL, and 10 mg / mL respectively. After 4 hours of incubation, count the results.

[0145] 3.2 Colony Count

[0146] Take 1 mL of the bacterial culture to be counted using a pipette and place it in 9 mL of LB liquid medium. Mix thoroughly. Then, take 1 mL of the culture using a new pipette and add it to another 9 mL of LB liquid medium. Mix thoroughly. Repeat this process to perform a 10-fold serial dilution.

[0147] 3.3 Counting Culture

[0148] Aseptic technique was employed. 1 mL of each dilution of bacterial culture was added to a sterile Petri dish. 15-20 mL of melted and incubated nutrient agar medium (46-48℃) was added to each dish and thoroughly mixed. The dishes were then capped and allowed to solidify. After solidification, the dishes were inverted and incubated at 35±1℃ (28±1℃ for Candida albicans and Aspergillus niger) for 48 hours. After incubation, the number of bacterial colonies in each dilution of Petri dish was calculated.

[0149] 4. Counting Rules

[0150] Select dilution plates with an average colony count within the range (bacteria: 30–300, fungi: 30–100) for counting. If all counts are less than 30, select the lowest dilution result for counting. Multiply the count result by the corresponding dilution level to obtain the final bacterial count of the test solution.

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

[0152] Where N: viable bacteria count;

[0153] C: Colony count; (The number of colonies grown in the petri dish)

[0154] D: Dilution factor.

[0155] Antibacterial rate calculation: Antibacterial rate = (Initial bacterial culture quantity - Sample liquid viable bacteria quantity) / Initial bacterial culture quantity.

[0156] Table 2

[0157]

[0158] Table 3

[0159]

[0160] Table 4

[0161]

[0162] analyze:

[0163] Combine Table 2-4 and Figure 23-28 As shown, different concentrations of the product all have a certain antibacterial effect against Staphylococcus aureus, with 10 mg / mL being the best. The antibacterial rates of the products prepared in Examples 1, 3, and 5 were 96%, 100%, and 97%, respectively.

[0164] Summarize:

[0165] This invention uses olefins as bridging units to achieve a three-component pyridine derivatization reaction with alkylboronic acid as the core, induced by visible light under the action of a base. The reaction conditions are mild, the raw materials are inexpensive and readily available, the operation process is simple, and the reaction has broad applicability. It can effectively replace the synthesis of traditional complex pyridine derivatives without the need for complex substrate design. At the same time, since the pyridine-based compound has high pharmacological activity, it has been widely used in biomedicine such as antitumor, anticancer, and antibacterial applications.

[0166] It is understood that the above detailed description of the present invention is for illustrative purposes only and is not intended to limit the technical solutions described in the embodiments of the present invention. Those skilled in the art should understand that modifications or equivalent substitutions can still be made to the present invention to achieve the same technical effects; as long as the usage requirements are met, they are all within the protection scope of the present invention.

Claims

1. The application of a pyridine derivative compound in the preparation of antibacterial drugs, characterized in that: The pyridine derivatives are selected from one of the following compounds: 。 2. The application of a pyridine derivative compound according to claim 1 in the preparation of antibacterial drugs, characterized in that: The pyridine derivatives were prepared by the following method: 2.0 mL of acetone was added to a 4 mL transparent glass bottle equipped with a magnetic stir bar and a rubber stopper. Then, 0.2 mmol of 4-cyanopyridine, 5.0 mol% of [Ir(dtbbpy)(ppy)2][PF6], 0.6 mmol of 4-methylstyrene, 0.2 mmol of K3PO4, and 0.4 mmol of cyclopentylboronic acid were added to the bottle. The reaction mixture was reacted at ambient temperature under a 3W blue LED at 420 nm for 24 hours. After the reaction, the solid was centrifuged, and the organic layer was concentrated. The crude mixture was eluted with EA:PE = 1:10, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified to obtain the desired product. 。 3. The application of a pyridine derivative compound according to claim 1 in the preparation of antibacterial drugs, characterized in that: The pyridine derivatives were prepared by the following method: 2.0 mL of acetone was added to a 4 mL transparent glass bottle equipped with a magnetic stir bar and a rubber stopper. Then, 0.2 mmol of 4-cyanopyridine, 5.0 mol% of [Ir(dtbbpy)(ppy)2][PF6], 0.6 mmol of 4-fluorostyrene, 0.2 mmol of K3PO4, and 0.4 mmol of cyclopentylboronic acid were added to the bottle. The reaction mixture was reacted at ambient temperature under a 3W blue LED at 420 nm for 24 hours. After the reaction, the solid was centrifuged, and the organic layer was concentrated. The crude mixture was eluted with EA:PE = 1:10, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified to obtain the desired product. 。 4. The application of a pyridine derivative compound according to claim 1 in the preparation of antibacterial drugs, characterized in that: The pyridine derivatives were prepared using the following method: 2.0 mL of acetone was added to a 4 mL transparent glass bottle equipped with a magnetic stir bar and a rubber stopper. Then, 0.2 mmol of 4-cyano-3-fluoropyridine, 5.0 mol% of [Ir(dtbbpy)(ppy)2][PF6], 0.6 mmol of 4-methylstyrene, 0.2 mmol of K3PO4, and 0.4 mmol of cyclopentylboronic acid were added to the bottle. The reaction mixture was reacted at ambient temperature under a 3W blue LED at 420 nm for 24 hours. After the reaction, the solid was centrifuged, and the organic layer was concentrated. The crude mixture was eluted with EA:PE = 1:10, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified to obtain the desired product. 。

Images