CN118440080B - Triphenylamine cationic compound and preparation method and application thereof - Google Patents
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Abstract
本发明公开了三苯胺类阳离子化合物及其制备方法和应用。三苯胺类阳离子化合物的结构式如式(III)所示，其制备方法包括：以双(2‑吡啶基)甲酮(a)或吡啶‑2‑基(吡啶‑3‑基)甲酮(b)或吡啶‑2‑基(吡啶‑4‑基)甲酮(c)、对溴苯甲醛和乙酸铵为原料，制备产物(I)，或以双(2‑吡啶基)甲酮(a)、4‑二苯胺基苯甲醛和乙酸铵为原料，制备产物(IId)，产物(I)、4‑硼酸三苯胺和碳酸钾为原料，制备产物(IIa)或(IIb)或(IIc)，产物(IIa)或(IIb)或(IIc)或(IId)与碘甲烷为原料，制得产物三苯胺类阳离子化合物(III)。该三苯胺类阳离子化合物具有抗菌活性，可作为抗细菌试剂。The invention discloses a triphenylamine cationic compound and its preparation method and application. The structural formula of the triphenylamine cationic compound is shown in formula (III), and its preparation method includes: using bis(2-pyridyl) ketone (a) or pyridine-2-yl (pyridine-3-yl) ketone (b) or pyridine-2-yl (pyridine-4-yl) ketone (c), p-bromobenzaldehyde and ammonium acetate as raw materials, preparing product (I), or using bis(2-pyridyl) ketone (a), 4-diphenylamine benzaldehyde and ammonium acetate as raw materials, preparing product (IId), product (I), 4-boric acid triphenylamine and potassium carbonate as raw materials, preparing product (IIa) or (IIb) or (IIc), product (IIa) or (IIb) or (IIc) or (IId) and iodomethane as raw materials, preparing product triphenylamine cationic compound (III). The triphenylamine cationic compound has antibacterial activity and can be used as an antibacterial agent.
Description
Technical Field
The invention belongs to the technical field of antibiosis, and particularly relates to a triphenylamine cationic compound, a preparation method and application thereof.
Background
Bacterial infection is a common disease and is also a common source of deterioration of materials or products in industry. Severely threatens human health and industrial production. Although several classes of bactericides or agents are currently available both pharmaceutically and industrially, the self-survival ability of microorganisms has prompted some resistance to these agents with a long history of their use. The discovery of an anti-microbial agent of a completely new structure has become an important subject of research in this field. The high-throughput screening is one of methods for obtaining the anti-bactericides with brand-new structures, and the triphenylamine cationic compound obtained by screening can become the anti-bactericides with brand-new structures.
Disclosure of Invention
The invention aims to provide a triphenylamine cationic compound which has a novel structure and good antibacterial activity on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa.
The first object of the present invention is to provide a triphenylamine cationic compound having a structural formula shown in formula (III):
R is selected from
A second object of the present invention is to provide a process for producing the above triphenylamine cationic compound, which comprises the steps of reacting 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 and ammonium acetate as raw materials to obtain the first step product (Ia), (Ib), (Ic) or reacting bis (2-pyridyl) methanone (a), 4-diphenylaminobenzaldehyde and ammonium acetate as raw materials to obtain the first step product (IId), reacting the first step product (Ia) or (Ib) or (Ic), 4-triphenylamine borate and potassium carbonate as raw materials to obtain the second step product (IIa) or (IIb) or (IIc) or (IId) with iodomethane as raw materials to obtain the product triphenylamine cationic compound (IIIa), (IIIb), (IIId) as raw materials, and synthesizing the product of the above triphenylamine cationic compound of the formula
Preferably, the method comprises the steps of 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 into a reactor, heating and stirring to react to obtain a first product (Ia), (Ib) or (Ic), or adding bis (2-pyridyl) methanone (a), 4-diphenylamino benzaldehyde, ammonium acetate and glacial acetic acid into the reactor, heating and stirring to react to obtain a first product (IId), adding the first product (Ia) or (Ib) or (Ic), triphenylamine 4-borate, potassium carbonate, tetraphenylphosphine palladium, tetrahydrofuran and water into the reactor, heating and stirring to react to obtain a second product (IIIb) or (IIc), adding the second product (IIb) or (IIc) or the first product (IIId), iodine and methane into the reactor, and stirring to obtain a cationic compound (IIIb), (IIIc) or (IIIc).
Preferably, the ratio of the amounts of the substances of the bis (2-pyridyl) ketone (a) or the pyridin-2-yl (pyridin-3-yl) ketone (b) or the pyridin-2-yl (pyridin-4-yl) ketone (C), the p-bromobenzaldehyde and the ammonium acetate in the first step is 1:3:5, the ratio of the amounts of the substances of the bis (2-pyridyl) ketone (a), the 4-diphenylaminobenzaldehyde and the ammonium acetate in the first step is 1:1.5:4, and the heating and stirring reactions in the first step are all stirring reactions at 110 ℃.
Preferably, the ratio of the amounts of the product (I), the triphenylamine 4-borate and the potassium carbonate in the first step is 1:1.2:10, and the heating and stirring reaction is carried out at 90 ℃.
The total yield of the preparation method disclosed by the invention can be 5% -30%.
A third object of the present invention is to provide the use of the above triphenylamine-based cationic compound for preparing an antibacterial agent.
Preferably, the antibacterial agent is an anti-staphylococcus aureus, escherichia coli and/or pseudomonas aeruginosa agent.
A fourth object of the present invention is to provide an antibacterial agent containing the above triphenylamine-based cationic compound as an active ingredient.
Preferably, the antibacterial agent is an anti-staphylococcus aureus, escherichia coli and/or pseudomonas aeruginosa agent.
Preferably, the triphenylamine cationic compound has a concentration of 1-4. Mu.g/mL.
Compared with the prior art, the invention has the following beneficial effects:
The triphenylamine cationic compound synthesized by the invention is easy to synthesize, shows good antibacterial activity, has good antibacterial activity on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa, and has a great application value in the field of antibacterial technology as a triphenylamine cationic compound with a brand new structure.
Detailed Description
The synthetic reaction formulas of triphenylamine cationic compounds IIIa, IIIb, IIIc and IIId are as follows:
the following examples are further illustrative of the invention and are not intended to be limiting thereof.
Example 1:
preparation of 2- (3- (4 '- (diphenylamino) - [1,1' -biphenyl ] -4-yl) imidazo [1,5-a ] pyridin-1-yl) -1-methylpyridin-1-ium iodized salt (IIIa):
5mmol of bis (2-pyridyl) methanone, 15mmol of p-bromobenzaldehyde, 25mmol of ammonium acetate and 30mL of glacial acetic acid are added into a 100mL flask, the mixture is stirred and reacted for 12 hours at 110 ℃ under nitrogen, after the reaction is finished, the mixture is cooled and poured into 300mL of ice water, the mixture is stood for 2 hours, suction filtration, filter residue is washed by cold ethanol, ethanol is recrystallized, and the product (Ia) is obtained, and the yield is 70%.
4Mmol of the first-step product (Ia), 4.8mmol of triphenylamine 4-borate, 0.08mmol of tetraphenylphosphine palladium, 40mmol of potassium carbonate, 60mL of tetrahydrofuran and 5mL of water are added into a 100mL flask, stirred and reacted for 24 hours at 90 ℃ under nitrogen, after the reaction is finished, the mixture is dried under reduced pressure, silica gel column chromatography is purified (200-300 meshes, eluent is ethyl acetate: petroleum ether (60-90 ℃), gradient elution: petroleum ether for 10min, volume fraction of 0-20% ethyl acetate for 20min, volume fraction of 20% ethyl acetate for 10min, volume fraction of 20-100% ethyl acetate for 20min, ethyl acetate for 10 min) is carried out, the product (IIa) is obtained after the product is collected under the section of 20% ethyl acetate, rf value of 0.25 (volume ratio ethyl acetate: petroleum ether=1:3) and yield of 52% is obtained after the product is dried under reduced pressure.
Adding 0.39mmol of the second step product (IIa), 10mL of dichloromethane and 1mL of methyl iodide into a 30mL reaction kettle, stirring and reacting for 5 days at a temperature of light-shielding 30 ℃, after the reaction is finished, air-drying, purifying by silica gel column chromatography (200-300 meshes, eluent is methanol: dichloromethane, gradient elution is dichloromethane for 10min, volume fraction is 0-40% methanol for 20min, volume fraction is 40% methanol for 10min, volume fraction is 40-100% methanol for 20min and methanol for 10 min), collecting the product under 40% methanol for 10min to obtain a product (IIIa), rf value is 0.43 (volume ratio formic acid: methanol=1:9), yield 38％.1H 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 C37H29N4 +:529.2386[M]+;found:529.2400.
Example 2:
preparation of 3- (3- (4 '- (diphenylamino) - [1,1' -biphenyl ] -4-yl) imidazo [1,5-a ] pyridin-1-yl) -1-methylpyridin-1-ium iodized salt (IIIb):
5mmol of pyridin-2-yl (pyridin-3-yl) methanone, 15mmol of p-bromobenzaldehyde, 25mmol of ammonium acetate and 30mL of glacial acetic acid are added into a 100mL flask, stirred at 110 ℃ under nitrogen for reaction for 24 hours, after the reaction is completed, the mixture is cooled, a majority of solvent is removed by rotary evaporation under reduced pressure, the mixture is poured into 150mL of ice water, standing for 4 hours, suction filtration and silica gel column chromatography purification (200-300 meshes, eluent is ethyl acetate: petroleum ether (60-90 ℃), gradient elution: petroleum ether for 10 minutes, volume fraction of 0-30% ethyl acetate for 20 minutes, volume fraction of 30% ethyl acetate for 10 minutes, volume fraction of 30-100% ethyl acetate for 20 minutes, ethyl acetate for 10 minutes) are carried out, a product which emits blue light by 365nm light irradiation under a section of 30% ethyl acetate for 10 minutes is collected, and after the reduction of pressure, the product (Ib) is obtained, rf value of 0.1 (volume ratio ethyl acetate: petroleum ether=1:3) is obtained, and yield 21%.
1Mmol of the first-step product (Ib), 1.2mmol of triphenylamine 4-borate, 0.02mmol of tetraphenylphosphine palladium, 10mmol of potassium carbonate, 15mL of tetrahydrofuran and 2mL of water are added into a 100mL flask, stirring is carried out for 24 hours at a temperature of 90 ℃ under nitrogen, after the reaction is finished, dichloromethane/water (1/1, v/v) is extracted for 3 times after decompression and spin-drying is carried out, a dichloromethane phase is collected, silica gel column chromatography purification (200-300 meshes, eluent is ethyl acetate: petroleum ether (60-90 ℃) is carried out, gradient elution is carried out for 10min of petroleum ether, the volume fraction is 0-100% of ethyl acetate is 60min, ethyl acetate is 30 min), a product which emits blue yellow light under 365nm light at a 60min section of ethyl acetate is collected, and after decompression and spin-drying, the product (IIb) is obtained, wherein Rf value is 0.51 (volume ratio of ethyl acetate: petroleum ether=1:1), and yield is 68%.
Adding 1mmol of the second-step product (IIb), 15mL of dichloromethane and 1mL of methyl iodide into a 30mL reaction kettle, stirring and reacting for 4 days at a temperature of 30 ℃ in the absence of light, after the reaction is finished, air-drying, purifying by silica gel column chromatography (200-300 meshes, eluent is methanol: dichloromethane, gradient elution is dichloromethane for 10min, volume fraction is 0-20% methanol for 20min, volume fraction is 20% methanol for 10min, volume fraction is 20-100% methanol for 20min, methanol for 10 min), collecting the product under the section of 20% methanol for 10min, obtaining a product (IIIb), rf value of 0.38 (volume ratio formic acid: methanol=1:9), yield 38％.1H 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,1H,pyridine),7.10(m,6H,benzene),7.01(t,1H,pyridine),4.47(s,3H,methyl).HRMS(ESI):m/z calcd for C37H29N4 +:529.2386[M]+;found:529.2401.
Example 3:
Preparation of 4- (3- (4 '- (diphenylamino) - [1,1' -biphenyl ] -4-yl) imidazo [1,5-a ] pyridin-1-yl) -1-methylpyridin-1-ium iodized salt (IIIc):
10mmol of pyridin-2-yl (pyridin-4-yl) methanone, 30mmol of p-bromobenzaldehyde, 50mmol of ammonium acetate and 60mL of glacial acetic acid are added into a 100mL flask, stirred and reacted for 24 hours at 110 ℃ under nitrogen, after the reaction is completed and dried under reduced pressure, silica gel column chromatography is performed (200-300 meshes, eluent is ethyl acetate: petroleum ether (60-90 ℃) and gradient elution: petroleum ether 10min, volume fraction of 0-50% ethyl acetate 20min, volume fraction of 50% ethyl acetate 10min, volume fraction of 50-100% ethyl acetate 20min and ethyl acetate 10 min) is performed, 365nm light irradiation blue light-emitting product under the section of 50% ethyl acetate 10min is collected, and after the reduced pressure drying, the product (Ic) is obtained, rf value of 0.25 (volume ratio ethyl acetate: petroleum ether=1:1) and yield of 52%.
1Mmol of the first-step product (Ic), 1.2mmol of triphenylamine 4-borate, 0.02mmol of tetraphenylphosphine palladium, 10mmol of potassium carbonate, 15mL of tetrahydrofuran and 2mL of water are added into a 100mL flask, stirred and reacted for 24 hours at 90 ℃ under nitrogen, after the reaction is finished, dichloromethane/water (1/1, v/v) is extracted for 3 times after decompression and spin-drying, a dichloromethane phase is collected, silica gel column chromatography is carried out for purification (200-300 meshes, eluent is ethyl acetate: petroleum ether (60-90 ℃), gradient elution is carried out for 10min, volume fraction is 0-100% of ethyl acetate for 60min, ethyl acetate for 30 min), a product which emits yellow light when 365nm light is collected about 70% of ethyl acetate is obtained after decompression and spin-drying, rf value is 0.74 (ethyl acetate), and yield is 52%.
Adding 0.26mmol of the second-step product (IIc), 10mL of dichloromethane and 1mL of methyl iodide into a 30mL reaction kettle, stirring and reacting for 24 hours at a dark state and 30 ℃, filtering after the reaction is finished, and air-drying filter residues to obtain a product (IIIc) in a yield 38％.1H NMR(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/z calcd for C37H29N4 +:529.2386[M]+;found:529.2407.
Example 4:
Preparation of 2- (3- (4- (diphenylamino) phenyl) imidazo [1,5-a ] pyridin-1-yl) -1-methylpyridin-1-ium iodized salt (IIId):
5mmol of bis (2-pyridyl) methanone, 7.5mmol of 4-diphenylaminobenzaldehyde, 20mmol of ammonium acetate and 30mL of glacial acetic acid are added into a 100mL flask, the mixture is stirred and reacted for 24 hours at 110 ℃ under nitrogen, after the reaction is finished, the mixture is cooled and poured into 150mL of ice water, the mixture is stood for 1 hour, suction filtration is carried out, and filter residues are recrystallized by ethyl acetate to obtain a product (IId) with the yield of 78%.
Adding 0.68mmol of the second-step product (IId), 15mL of dichloromethane and 1mL of methyl iodide into a 30mL reaction kettle, stirring and reacting for 5 days at a temperature of light-shielding 30 ℃, after the reaction is finished, air-drying, purifying by silica gel column chromatography (200-300 meshes, eluent is methanol: dichloromethane, gradient elution is dichloromethane for 5min, volume fraction is 0-5% methanol for 10min, volume fraction is 5-100% methanol for 20min and methanol for 10 min), collecting the product under the section of 5% methanol for 10min to obtain a product (IIId), rf value is 0.71 (volume ratio methanol: dichloromethane=1:6), and yield 38％.1H 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 and pyridine),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 C31H25N4 +:453.2073[M]+;found:453.2093.
Example 5:
antibacterial Activity test of the target Compound:
The MIC of the target compound (triphenylamine cationic compound prepared in examples 1 to 4) was measured by a microdilution method using 2-methyl-4-isothiazolin-3-one (MIT) as a positive control reagent, and the antibacterial activity of the target compound (Staphylococcus aureus ATCC 6538P), escherichia coli (ESCHERICHIA COLI ATCC 8739), pseudomonas aeruginosa (Pseudomonas aeruginosaATCC 9027) was measured.
The experimental procedure of the microdilution method is as follows:
200. Mu.L of an aqueous solution to be measured (2-methyl-4-isothiazolin-3-one and the triphenylamine cationic compound prepared in examples 1 to 4) having a concentration of 256. Mu.g/mL was added to column 1 of a 96-well plate, 100. Mu.L of MH broth was added to each of columns 2 to 12, 100. Mu.L of the aqueous solution was added to column 2 to mix, 100. Mu.L of the aqueous solution was added to column 3 to mix, and so forth, and finally 100. Mu.L of the aqueous solution was added to column 11 to mix, and 100. Mu.L of the excess solution was removed to discard the solution. 100 mu L of bacterial liquid with the concentration of 10 6 cfu/mL is added into each of the 1 st to 11 th columns, 100 mu L of bacterial liquid with the concentration of 10 6 cfu/mL is added into the four holes before the 12 th column, 100 mu L of MH broth is added into the four holes after the 12 th column, the final volume of each hole is 200 mu L, the concentrations of samples to be detected in the 1 st to 11 th columns are 128, 64, 32, 16, 8, 4, 2, 1, 0.5, 0.25 and 0.125 mu g/mL in sequence, the four holes before the 12 th column are no-bacterial-addition (bacterial-growth control), and the four holes after the 12 th column are no-bacterial-addition (sterile blank control). Three replicates were made for each sample tested. After incubation of the 96-well plates in a 37 ℃ oven for 24 hours, the concentration of wells with OD 600 values, OD 600 values close to the sterile blank, was the minimum inhibitory concentration MIC.
The results show that:
(1) The MIC of 2- (3- (4 '- (diphenylamino) - [1,1' -biphenyl ] -4-yl) imidazo [1,5-a ] pyridin-1-yl) -1-methylpyridin-1-ium iodide salt (IIIa) on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa was 1 μg/mL, 1 μg/mL and 1 μg/mL, respectively.
(2) The MIC of 3- (3- (4 '- (diphenylamino) - [1,1' -biphenyl ] -4-yl) imidazo [1,5-a ] pyridin-1-yl) -1-methylpyridin-1-ium iodide (IIIb) on Staphylococcus aureus, escherichia coli and Pseudomonas aeruginosa was 4 μg/mL, 2 μg/mL and 2 μg/mL, respectively.
(3) The MIC of the 4- (3- (4 '- (diphenylamino) - [1,1' -biphenyl ] -4-yl) imidazo [1,5-a ] pyridin-1-yl) -1-methylpyridin-1-ium iodide salt (IIIc) on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa was 2 μg/mL, 1 μg/mL and 1 μg/mL, respectively.
(4) The MIC of 2- (3- (4- (diphenylamino) phenyl) imidazo [1,5-a ] pyridin-1-yl) -1-methylpyridin-1-ium iodized salt (IIId) on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa is 2 mug/mL, 2 mug/mL and 2 mug/mL respectively.
The foregoing is merely a preferred embodiment of the present invention, and it should be noted that the above-mentioned preferred embodiment should not be construed as limiting the invention, and the scope of the invention should be defined by the appended claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and such modifications and adaptations are intended to be comprehended within the scope of the invention.
Claims (10)
1. Triphenylamine cationic compound, the structural formula of which is shown in formula (III):
formula (III)
R is selected from、、Or (b)。
2. A process for producing a triphenylamine-based cationic compound according to claim 1, which comprises the steps of reacting 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 and ammonium acetate as raw materials to give a first-step product (Ia), (Ib), (Ic) or bis (2-pyridyl) methanone (a), 4-diphenylaminobenzaldehyde and ammonium acetate as raw materials to give a first-step product (IId), reacting the first-step product (Ia) or (Ib) or (Ic), 4-triphenylamine borate with potassium carbonate as raw materials to give a second-step product (IIa) or (IIb) or (IIc) or (IId) with iodomethane as raw materials to give a product of a triphenylamine-based cationic compound (IIIa), (IIIb), (c) or (IId) as raw materials, and synthesizing a product of the triphenylamine-based cationic compound of the formula (IIIa), (d)
。
3. The process according to claim 2, wherein the process comprises a first step of 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 the reactor, a heating and stirring reaction to obtain a first step of products (Ia), (Ib), (Ic) or adding bis (2-pyridyl) methanone (a), 4-diphenylamino benzaldehyde, ammonium acetate and glacial acetic acid to the reactor, a heating and stirring reaction to obtain a first step of products (IId), a second step of products (Ia) or (Ib) or (IIIb) or (IIb) or (IIc) obtained by adding the first step of products (Ia) or (Ic), triphenylamine 4-borate, potassium carbonate, tetraphenylphosphine palladium, tetrahydrofuran and water to the reactor, a second step of products (IIIb) or (IIIb) obtained by heating and stirring reaction, and a third step of products (IIb) or (IIc) obtained by adding the second step of products (IIb) or (IIIb) or (IIIc) to the first step of products (IIIb) or (d) and a) obtained by stirring reaction to obtain cationic compounds.
4. The process according to claim 3, wherein the amount ratio of the 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 and ammonium acetate is 1:3:5, the amount ratio of the bis (2-pyridyl) methanone (a), 4-diphenylaminobenzaldehyde and ammonium acetate is 1:1.5:4, and the heating and stirring reactions in the first step are all stirred at 110 ℃.
5. The preparation method according to claim 3, wherein the amount ratio of the substances of the first step product (I), the 4-triphenylamine borate and the potassium carbonate in the second step is 1:1.2:10, and the heating and stirring reaction is carried out at 90 ℃.
6. Use of a triphenylamine-based cationic compound according to claim 1 for the preparation of an antibacterial agent.
7. The use according to claim 6, wherein the antibacterial agent is an anti-staphylococcus aureus, escherichia coli and/or pseudomonas aeruginosa agent.
8. An antibacterial agent comprising the triphenylamine-based cationic compound according to claim 1 as an active ingredient.
9. The antibacterial agent of claim 8, wherein the antibacterial agent is an anti-staphylococcus aureus, escherichia coli and/or pseudomonas aeruginosa agent.
10. The antibacterial agent according to claim 8, wherein the concentration of the triphenylamine-based cationic compound is 1 to 4 μg/mL.
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| CN1930159A (en) * | 2004-03-08 | 2007-03-14 | 北卡罗来纳大学查珀尔希尔分校 | Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8,-tetrahydro-imidazo[1,2,-a]pyridines as antiprotozoal agents |
| CN101784191A (en) * | 2007-04-26 | 2010-07-21 | 先正达参股股份有限公司 | 4-aza indole derivatives and their use as fungicides |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1930159A (en) * | 2004-03-08 | 2007-03-14 | 北卡罗来纳大学查珀尔希尔分校 | Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8,-tetrahydro-imidazo[1,2,-a]pyridines as antiprotozoal agents |
| CN101784191A (en) * | 2007-04-26 | 2010-07-21 | 先正达参股股份有限公司 | 4-aza indole derivatives and their use as fungicides |
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