Triphenylamine cationic compounds and preparation methods and applications thereof
By developing tripaniline cationic compounds, the anti-effect problem of existing antibacterial agents on drug-resistant bacteria was solved, effective inhibition of Staphylococcus aureus, E. coli and Pseudomonas aeruginosa was achieved, and antibacterial with a new structure was provided. agent application.
Patent Information
- Application Number
- CN202410562936.7
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2024-05-08
- Publication Date
- 2024-12-20
- Estimated Expiration
- 2044-05-08
AI Technical Summary
Due to the long-term use of existing antibacterial agents, it is difficult to effectively fight bacteria such as Staphylococcus aureus, E. coli and Pseudomonas aeruginosa, and lacks new structures of antibacterial agents.
A tripaniline cationic compound was developed, prepared by specific synthetic methods, including the use of bis(2-pyridyl)methosterone, parabenzaldehyde, ammonium acetate, tripaniline 4-borate and potassium carbonate, etc., through multiple The reaction step gives a tripaniline cationic compound with antibacterial activity and is applied to an antibacterial reagent.
The synthesized tripaniline cationic compounds show good antibacterial activity, have significant antibacterial effects on Staphylococcus aureus, E. coli and Pseudomonas aeruginosa, provide a new structure of antibacterial agent solution, and have a large application. value.
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Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of antibacterial, and in particular relates to a triphenylamine cationic compound and a preparation method and application thereof. Background Art
[0002] Bacterial infection is a common disease and a common source of material or product deterioration in industry. It poses a serious threat to human health and industrial production. Although there are several types of bactericides or agents available in medicine and industry, with the long history of use of these agents, the self-survival ability of microorganisms has led to a certain degree of drug resistance. Discovering new antibacterial / bactericidal agents has become an important research topic in this field. High-throughput screening is one of the methods to obtain new antibacterial / bactericidal agents. The triphenylamine cationic compounds obtained by screening may become new antibacterial / bactericidal agents. Summary of the invention
[0003] The purpose of the present invention is to provide a triphenylamine cationic compound with novel structure and good antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa.
[0004] The first object of the present invention is to provide a triphenylamine cationic compound, the structural formula of the triphenylamine cationic compound is shown in formula (III):
[0005]
[0006] The R is selected from
[0007] The second object of the present invention is to provide a method for preparing the above-mentioned triphenylamine cationic compound, which comprises the following steps: using bis(2-pyridyl)ketone (a) or pyridin-2-yl(pyridin-3-yl)ketone (b) or pyridin-2-yl(pyridin-4-yl)ketone (c), p-bromobenzaldehyde and ammonium acetate as raw materials, reacting to obtain the first-step products (Ia), (Ib), (Ic); or using bis(2-pyridyl)ketone (a), 4-diphenylaminobenzaldehyde and ammonium acetate as raw materials, reacting to obtain the first-step products (Ia), (Ib), (Ic). The first step product (Ia) or (Ib) or (Ic), 4-boric acid triphenylamine and potassium carbonate are used as raw materials to react to obtain the second step product (IIa) or (IIb) or (IIc); the second step product (IIa) or (IIb) or (IIc) or the first step product (IId) and iodomethane are used as raw materials to react to obtain triphenylamine cationic compounds (IIIa), (IIIb), (IIIc), (IIId). The synthesis reaction formula of the triphenylamine cationic compound is:
[0008]
[0009]
[0010] Preferably, the method comprises the following steps: the first step: adding bis(2-pyridyl)methanone (a) or pyridin-2-yl(pyridin-3-yl)methanone (b) or pyridin-2-yl(pyridin-4-yl)methanone (c), p-bromobenzaldehyde, ammonium acetate and glacial acetic acid to a reactor, heating and stirring to react, to obtain the first-step products (Ia), (Ib) and (Ic); or adding bis(2-pyridyl)methanone (a), 4-diphenylaminobenzaldehyde, ammonium acetate and glacial acetic acid to a reactor, heating and stirring to react, to obtain the first-step product (IId); the second step: The first step product (Ia) or (Ib) or (Ic), 4-boric acid triphenylamine, potassium carbonate, tetrakistriphenylphosphine palladium, tetrahydrofuran and water are added to a reactor, heated and stirred for reaction, and the second step product (IIa) or (IIb) or (IIc) is obtained; the third step: the second step product (IIa) or (IIb) or (IIc) or the first step product (IId), iodomethane and dichloromethane are added to a reactor, stirred for reaction, and triphenylamine cationic compounds (IIIa), (IIIb), (IIIc) and (IIId) are obtained.
[0011] Preferably, the molar ratio of the bis(2-pyridyl)ketone (a) or pyridin-2-yl(pyridin-3-yl)ketone (b) or pyridin-2-yl(pyridin-4-yl)ketone (c), p-bromobenzaldehyde and ammonium acetate described in the first step is 1:3:5, the molar ratio of the bis(2-pyridyl)ketone (a), 4-diphenylaminobenzaldehyde and ammonium acetate described in the first step is 1:1.5:4, and the heating and stirring reaction described in the first step is a stirring reaction at 110°C.
[0012] Preferably, the ratio of the first step product (I), 4-triphenylamine borate and potassium carbonate in the second step is 1:1.2:10; and the heating and stirring reaction is a stirring reaction at 90°C.
[0013] The total yield of the preparation method of the present invention can be between 5% and 30%.
[0014] The third object of the present invention is to provide the use of the above-mentioned triphenylamine cationic compound in the preparation of antibacterial agents.
[0015] Preferably, the antibacterial agent is an agent against Staphylococcus aureus, Escherichia coli and / or Pseudomonas aeruginosa.
[0016] A fourth object of the present invention is to provide an antibacterial agent comprising the above-mentioned triphenylamine type cationic compound as an active ingredient.
[0017] Preferably, the antibacterial agent is an agent against Staphylococcus aureus, Escherichia coli and / or Pseudomonas aeruginosa.
[0018] Preferably, the concentration of the triphenylamine cationic compound is 1-4 μg / mL.
[0019] Compared with the prior art, the present invention has the following beneficial effects:
[0020] The triphenylamine cationic compound synthesized by the invention is easy to synthesize and shows good antibacterial activity, and has good antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. As a triphenylamine cationic compound with a completely new structure, it has great application value in the field of antibacterial technology. DETAILED DESCRIPTION
[0021] The synthesis reaction formula of the triphenylamine cationic compounds IIIa, IIIb, IIIc and IIId of the present invention is:
[0022]
[0023]
[0024] The following examples are provided to further illustrate the present invention, rather than to limit the present invention.
[0025] Embodiment 1:
[0026] Preparation steps of 2-(3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)imidazo[1,5-a]pyridin-1-yl)-1-methylpyridin-1-ium iodide (IIIa):
[0027]
[0028] 5 mmol of bis(2-pyridyl)methanone, 15 mmol of p-bromobenzaldehyde, 25 mmol of ammonium acetate and 30 mL of glacial acetic acid were added to a 100 mL flask, and the mixture was stirred at 110° C. under nitrogen for 12 hours. After the reaction was completed, the mixture was cooled and poured into 300 mL of ice water, and allowed to stand for 2 hours. The mixture was filtered, and the residue was washed with cold ethanol. The residue was recrystallized with ethanol to obtain the product (Ia) with a yield of 70%.
[0029] 4 mmol of the first step product (Ia), 4.8 mmol of 4-boric acid triphenylamine, 0.08 mmol of tetrakistriphenylphosphine palladium, 40 mmol of potassium carbonate, 60 mL of tetrahydrofuran and 5 mL of water were added to a 100 mL flask, and the mixture was stirred and reacted at 90° C. under nitrogen for 24 hours. After the reaction was completed, the mixture was evaporated under reduced pressure and purified by silica gel column chromatography (200-300 mesh, eluent was ethyl acetate: petroleum ether (60-90° C.), gradient elution: petroleum ether for 10 min, 0-20% ethyl acetate by volume for 20 min, 20% ethyl acetate by volume for 10 min, 20-100% ethyl acetate by volume for 20 min, ethyl acetate for 10 min), and the product under the 20% ethyl acetate 10 min section was collected and evaporated under reduced pressure to obtain product (IIa), with an Rf value of 0.25 (volume ratio of ethyl acetate: petroleum ether=1:3) and a yield of 52%.
[0030] 0.39 mmol of the second step product (IIa), 10 mL of dichloromethane and 1 mL of iodomethane were added to a 30 mL reactor, and the reaction was stirred at 30° C. in the dark for 5 days. After the reaction was completed, the mixture was air-dried and purified by silica gel column chromatography (200-300 mesh, eluent was methanol:dichloromethane, gradient elution: dichloromethane for 10 min, 0-40% methanol by volume for 20 min, 40% methanol by volume for 10 min, 40-100% methanol by volume for 20 min, methanol for 10 min), and the product in the 40% methanol 10 min section was collected to obtain product (IIIa) with an Rf value of 0.43 (volume ratio of formic acid:methanol=1:9) and a yield of 38%. 1 H NMR(600MHz,DMSO-d6,δ):9.06(d,1H,pyridine),8.77(d,1H,pyridine),8.57(t,1H,pyridine),8.38(d,1H,pyridine),8.02(m,4H,pyridine and benzene),7.91(d,2H,benzene),7.73(d,2H,benzene),7.41(t,1H,pyridine),7.37(t,4H,benzene),7.10(m,9H,benzene and pyridine),4.54(s,3H,methyl).HRMS(ESI):m / zcalcd for C 37 H 29 N4 + :529.2386[M] + ;found:529.2400.
[0031] Embodiment 2:
[0032] Preparation steps of 3-(3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)imidazo[1,5-a]pyridin-1-yl)-1-methylpyridin-1-ium iodide (IIIb):
[0033]
[0034] 5 mmol of pyridin-2-yl (pyridin-3-yl) ketone, 15 mmol of p-bromobenzaldehyde, 25 mmol of ammonium acetate and 30 mL of glacial acetic acid were added to a 100 mL flask, and the mixture was stirred and reacted at 110° C. under nitrogen for 24 hours. After the reaction was completed, the mixture was cooled, most of the solvent was removed by vacuum evaporation, and the mixture was poured into 150 mL of ice water. The mixture was allowed to stand for 4 hours, filtered, and purified by silica gel column chromatography (200-300 mesh, eluent was ethyl acetate: petroleum ether (60-90° C.), gradient elution: petroleum ether for 10 min, 0-30% ethyl acetate by volume for 20 min, 30% ethyl acetate by volume for 10 min, 30-100% ethyl acetate by volume for 20 min, ethyl acetate for 10 min), and the product emitting blue light under 365 nm light irradiation in the 10 min section of 30% ethyl acetate was collected, and the product (Ib) was obtained after vacuum evaporation with an Rf value of 0.1 (volume ratio of ethyl acetate: petroleum ether=1:3) and a yield of 21%.
[0035] 1 mmol of the first step product (Ib), 1.2 mmol of 4-boric acid triphenylamine, 0.02 mmol of tetrakistriphenylphosphine palladium, 10 mmol of potassium carbonate, 15 mL of tetrahydrofuran and 2 mL of water were added to a 100 mL flask, and the mixture was stirred and reacted at 90° C. under nitrogen for 24 hours. After the reaction was completed, the mixture was dried under reduced pressure and extracted with dichloromethane / water (1 / 1, v / v) for 3 times. The dichloromethane phase was collected and purified by silica gel column chromatography (200-300 mesh, eluent was ethyl acetate: petroleum ether (60-90° C.), gradient elution: petroleum ether 10 min, volume fraction 0-100% ethyl acetate 60 min, ethyl acetate 30 min), and the product emitting blue-yellow light under 365 nm light irradiation in the 0-100% ethyl acetate 60 min section was collected. After reduced pressure and dried, the product (IIb) was obtained, with an Rf value of 0.51 (volume ratio ethyl acetate: petroleum ether=1:1), and a yield of 68%.
[0036] 1 mmol of the second step product (IIb), 15 mL of dichloromethane and 1 mL of iodomethane were added to a 30 mL reactor, and the reaction was stirred at 30° C. in the dark for 4 days. After the reaction was completed, the mixture was air-dried and purified by silica gel column chromatography (200-300 mesh, eluent: methanol:dichloromethane, gradient elution: dichloromethane for 10 min, 0-20% methanol by volume for 20 min, 20% methanol by volume for 10 min, 20-100% methanol by volume for 20 min, methanol for 10 min), and the product in the 20% methanol for 10 min section was collected to obtain product (IIIb) with an Rf value of 0.38 (volume ratio of formic acid:methanol=1:9) and a yield of 38%. 1 H NMR(600MHz,DMSO-d6,δ):9.45(s,1H,pyridine),9.06(d,1H,pyridine),8.80(d,1H,pyridine) ,8.68(d,1H,pyridine),8.34(d,1H,pyridine),8.16(t,1H,pyridine),8.00(d,2H,benzene),7. 90(d,2H,benzene),7.84(d,2H,benzene),7.73(d,2H,benzene),7.37(t,4H,benzene),7.29(t,1 H,pyridine),7.10(m,6H,benzene),7.01(t,1H,pyridine),4.47(s,3H,methyl).HRMS(ESI):m / z calcd forC 37 H 29 N4 + :529.2386[M] + ;found:529.2401.
[0037] Embodiment 3:
[0038] Preparation steps of 4-(3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)imidazo[1,5-a]pyridin-1-yl)-1-methylpyridin-1-ium iodide (IIIc):
[0039]
[0040] 10 mmol of pyridin-2-yl (pyridin-4-yl) ketone, 30 mmol of p-bromobenzaldehyde, 50 mmol of ammonium acetate and 60 mL of glacial acetic acid were added to a 100 mL flask, and the mixture was stirred and reacted at 110° C. under nitrogen for 24 hours. After the reaction was completed, the mixture was evaporated under reduced pressure and purified by silica gel column chromatography (200-300 mesh, eluent was ethyl acetate: petroleum ether (60-90° C.), gradient elution: petroleum ether for 10 min, 0-50% ethyl acetate by volume for 20 min, 50% ethyl acetate by volume for 10 min, 50-100% ethyl acetate by volume for 20 min, ethyl acetate for 10 min), and the product emitting blue light under 365 nm light irradiation in the 50% ethyl acetate 10 min section was collected, and the product (Ic) was obtained after being evaporated under reduced pressure and evaporated, with an Rf value of 0.25 (volume ratio of ethyl acetate: petroleum ether=1:1) and a yield of 52%.
[0041] 1 mmol of the first step product (Ic), 1.2 mmol of 4-boric acid triphenylamine, 0.02 mmol of tetrakistriphenylphosphine palladium, 10 mmol of potassium carbonate, 15 mL of tetrahydrofuran and 2 mL of water were added to a 100 mL flask, and the mixture was stirred and reacted at 90° C. under nitrogen for 24 hours. After the reaction was completed, the mixture was dried under reduced pressure and extracted with dichloromethane / water (1 / 1, v / v) for 3 times. The dichloromethane phase was collected and purified by silica gel column chromatography (200-300 mesh, eluent was ethyl acetate: petroleum ether (60-90° C.), gradient elution: petroleum ether 10 min, volume fraction 0-100% ethyl acetate 60 min, ethyl acetate 30 min), and the product that emitted yellow light under 365 nm light irradiation when the ethyl acetate content was about 70% was collected, and the product (IIc) was obtained after reduced pressure and dried under reduced pressure, with an Rf value of 0.74 (ethyl acetate) and a yield of 52%.
[0042] 0.26 mmol of the second step product (IIc), 10 mL of dichloromethane and 1 mL of iodomethane were added to a 30 mL reactor, and the mixture was stirred and reacted at 30° C. in the dark for 24 hours. After the reaction was completed, the mixture was filtered and the residue was air-dried to obtain the product (IIIc) with a yield of 38%. 1 HNMR(600MHz,DMSO-d6,δ):8.75(m,3H,pyridine),8.53(m,3H,pyridine),8.01(d,2H,benzene),7.92(d ,2H,benzene),7.74(d,2H,benzene),7.53(t,1H,pyridine),7.38(t,4H,benzene),7.09(m,9H,benzene and pyridine),4.24(s,3H,methyl).HRMS(ESI):m / zcalcd for C 37 H 29 N4+ :529.2386[M] + ;found:529.2407.
[0043] Embodiment 4:
[0044] Preparation steps of 2-(3-(4-(diphenylamino)phenyl)imidazo[1,5-a]pyridin-1-yl)-1-methylpyridin-1-ium iodide (IIId):
[0045]
[0046] 5 mmol of bis(2-pyridyl)methanone, 7.5 mmol of 4-diphenylaminobenzaldehyde, 20 mmol of ammonium acetate and 30 mL of glacial acetic acid were added to a 100 mL flask, and the mixture was stirred at 110° C. under nitrogen for 24 hours. After the reaction was completed, the mixture was cooled and poured into 150 mL of ice water, allowed to stand for 1 hour, and filtered. The residue was recrystallized from ethyl acetate to obtain the product (IId) with a yield of 78%.
[0047] 0.68 mmol of the second step product (IId), 15 mL of dichloromethane and 1 mL of iodomethane were added to a 30 mL reactor, and the reaction was stirred at 30°C in the dark for 5 days. After the reaction was completed, the mixture was air-dried and purified by silica gel column chromatography (200-300 mesh, eluent: methanol:dichloromethane, gradient elution: dichloromethane 5 min, 0-5% methanol by volume 10 min, 5% methanol by volume 10 min, 5-100% methanol by volume 20 min, methanol 10 min), and the product in the 5% methanol 10 min section was collected to obtain product (IIId) with an Rf value of 0.71 (volume ratio of methanol:dichloromethane = 1:6) and a yield of 38%. 1 H NMR(600MHz,DMSO-d6,δ):9.03(d,1H,pyridine),8.69(d,1H,pyridine),8.53(t,1H,pyridine),8.35(d, 1H,pyridine),8.01(d,1H,pyridine),7.95(t,1H,pyridine),7.82(d,2H,benzene),7.39(m,5H,benzene andpyridine),7.16(m,6H,benzene),7.12(d,2H,benzene),7.08(t,1H,pyridine),4.50(s,3H,methyl).HRMS(ESI):m / z calcd for C 31 H 25 N4 + :453.2073[M] +;found:453.2093.
[0048] Embodiment 5:
[0049] Antimicrobial activity test of target compounds:
[0050] The MIC of the target compound (triphenylamine cationic compound prepared in Example 1-4) was determined by microdilution method using 2-methyl-4-isothiazolin-3-one (MIT) as a positive control agent, and the antibacterial activity of the target compound (triphenylamine cationic compound prepared in Example 1-4) against Staphylococcus aureus (Staphylococcus aureus ATCC 6538P), Escherichia coli (Escherichia coli ATCC 8739), and Pseudomonas aeruginosa (Pseudomonas aeruginosa ATCC 9027) was determined.
[0051] The experimental steps of microdilution method are as follows:
[0052] Add 200 μL of a 256 μg / mL aqueous solution of the sample to be tested (2-methyl-4-isothiazoline-3-one and the triphenylamine cationic compound prepared in Examples 1-4) to the first column of the 96-well plate, add 100 μL of MH broth to columns 2-12 respectively, then take 100 μL from column 1 and add it to column 2 to mix, then take 100 μL from column 2 and add it to column 3 to mix, and so on, finally take 100 μL from column 10 and add it to column 11 to mix, then take out 100 μL of excess liquid and discard. Take 100 μL of 10 6 cfu / mL of bacterial solution was added to each well in columns 1-11, and 100 μL of the concentration of 10 6 cfu / mL of bacterial solution was added to the first four wells of the 12th column, and 100μL of MH broth was added to the last four wells of the 12th column. The final volume of each well was 200μL. The concentrations of the samples to be tested in columns 1-11 were 128, 64, 32, 16, 8, 4, 2, 1, 0.5, 0.25, and 0.125μg / mL, respectively. The first four wells of the 12th column were bacteria-free (bacterial growth control), and the last four wells of the 12th column were bacteria-free (sterile blank control). Three replicates were made for each sample to be tested. After the 96-well plate was incubated in a 37°C oven for 24 hours, the OD was measured using an enzyme reader. 600 Value, OD 600 The concentration of the wells with values close to the sterile blank control is the minimum inhibitory concentration (MIC).
[0053] The results show:
[0054] (1) The MICs of 2-(3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)imidazo[1,5-a]pyridin-1-yl)-1-methylpyridin-1-ium iodonium salt (IIIa) against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa were 1 μg / mL, 1 μg / mL, and 1 μg / mL, respectively.
[0055] (2) The MICs of 3-(3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)imidazo[1,5-a]pyridin-1-yl)-1-methylpyridin-1-ium iodide (IIIb) against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa were 4 μg / mL, 2 μg / mL, and 2 μg / mL, respectively.
[0056] (3) The MICs of 4-(3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)imidazo[1,5-a]pyridin-1-yl)-1-methylpyridin-1-ium iodonium salt (IIIc) against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa were 2 μg / mL, 1 μg / mL, and 1 μg / mL, respectively.
[0057] (4) The MICs of 2-(3-(4-(diphenylamino)phenyl)imidazo[1,5-a]pyridin-1-yl)-1-methylpyridin-1-ium iodide (IIId) against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa were 2 μg / mL, 2 μg / mL, and 2 μg / mL, respectively.
[0058] The above are only preferred embodiments of the present invention. It should be noted that the above preferred embodiments should not be regarded as limiting the present invention, and the protection scope of the present invention should be based on the scope defined by the claims. For ordinary technicians in this technical field, several improvements and modifications can be made without departing from the spirit and scope of the present invention, and these improvements and modifications should also be regarded as the protection scope of the present invention.
Claims
1. A triphenylamine cationic compound, wherein the structural formula of the triphenylamine cationic compound is shown in formula (III): Formula (III) The R is selected from , , ,or .
2. A method for preparing the triphenylamine cationic compound according to claim 1, characterized in that: The invention comprises the following steps: using bis(2-pyridyl) ketone (a) or pyridin-2-yl (pyridin-3-yl) ketone (b) or pyridin-2-yl (pyridin-4-yl) ketone (c), p-bromobenzaldehyde and ammonium acetate as raw materials to react to obtain first-step products (Ia), (Ib) and (Ic); or using bis(2-pyridyl) ketone (a), 4-diphenylaminobenzaldehyde and ammonium acetate as raw materials to react to obtain first-step product (IId); using first-step product (Ia) or (Ib) or (Ic), 4-triphenylamine borate and potassium carbonate as raw materials to react to obtain second-step product (IIa) or (IIb) or (IIc); using second-step product (IIa) or (IIb) or (IIc) or first-step product (IId) and iodomethane as raw materials to react to obtain triphenylamine cationic compounds (IIIa), (IIIb), (IIIc) and (IIId); the synthesis reaction formula of the triphenylamine cationic compound is: 。 3. The preparation method according to claim 2, characterized in that: The following steps are involved: The first step is to add bis(2-pyridyl)methanone (a) or pyridin-2-yl(pyridin-3-yl)methanone (b) or pyridin-2-yl(pyridin-4-yl)methanone (c), p-bromobenzaldehyde, ammonium acetate and glacial acetic acid into a reactor, and heat and stir to react to obtain the first-step products (Ia), (Ib) and (Ic); or add bis(2-pyridyl)methanone (a), 4-diphenylaminobenzaldehyde, ammonium acetate and glacial acetic acid into a reactor, and heat and stir to react to obtain the first-step product (IId); the second step is to add the first-step product (Ia) or (Ib) or (Ic), 4-boric acid triphenylamine, potassium carbonate, tetrakistriphenylphosphine palladium, tetrahydrofuran and water are added to a reactor, heated and stirred for reaction to obtain the second step product (IIa) or (IIb) or (IIc); the third step: the second step product (IIa) or (IIb) or (IIc) or the first step product (IId), iodomethane and dichloromethane are added to a reactor, stirred for reaction to obtain triphenylamine cationic compounds (IIIa), (IIIb), (IIIc) and (IIId).
4. The preparation method according to claim 3, characterized in that: The molar ratio of the bis(2-pyridyl)ketone (a) or pyridin-2-yl(pyridin-3-yl)ketone (b) or pyridin-2-yl(pyridin-4-yl)ketone (c), p-bromobenzaldehyde and ammonium acetate described in the first step is 1:3:5, the molar ratio of the bis(2-pyridyl)ketone (a), 4-diphenylaminobenzaldehyde and ammonium acetate described in the first step is 1:1.5:4, and the heating and stirring reaction described in the first step is a stirring reaction at 110°C.
5. The preparation method according to claim 3, characterized in that: In the second step, the molar ratio of the first step product (I), 4-triphenylamine borate and potassium carbonate is 1:1.2:10; and the heating and stirring reaction is a stirring reaction at 90°C.
6. Use of the triphenylamine cationic compound according to claim 1 in the preparation of antibacterial agents.
7. The use according to claim 6, characterized in that: The antibacterial agent is an agent against Staphylococcus aureus, Escherichia coli and / or Pseudomonas aeruginosa.
8. An antibacterial agent, characterized in that Contains the triphenylamine cationic compound according to claim 1 as an active ingredient.
9. The antibacterial agent according to claim 8, characterized in that The antibacterial agent is an agent against Staphylococcus aureus, Escherichia coli and / or Pseudomonas aeruginosa.
10. The antibacterial agent according to claim 8, characterized in that The concentration of the triphenylamine cationic compound is 1-4 μg / mL.