CN116947771A - 1, 2, 3-triazole sulfonamide derivative, and preparation method and application thereof - Google Patents

1, 2, 3-triazole sulfonamide derivative, and preparation method and application thereof Download PDF

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CN116947771A
CN116947771A CN202310979340.2A CN202310979340A CN116947771A CN 116947771 A CN116947771 A CN 116947771A CN 202310979340 A CN202310979340 A CN 202310979340A CN 116947771 A CN116947771 A CN 116947771A
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sulfonamide
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玄光善
李斌
孔竞尧
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Qingdao University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Environmental Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention discloses a 1, 2, 3-triazole sulfonamide derivative, a preparation method and application thereof. The compound has a general formula (A). The synthesis method is that sulfonamide is used as an initial raw material, diazotization and azide are coupled with acetoacetic ester to finish the butt joint of triazole ring and sulfonamide, and an amide bond is introduced into the structure of the sulfonamide, so that a series of novel 1, 2, 3-triazole sulfonamide derivatives are synthesized. Such compounds are useful for Escherichia coli and Pseudomonas aeruginosaBacteria, salmonella typhi, staphylococcus aureus, bacillus subtilis, strains such as candida albicans and aspergillus niger, pests and plant pathogenic bacteria in forestry and other fields all show excellent functions of bacteriostasis, disinsection, sterilization and the like.

Description

1, 2, 3-triazole sulfonamide derivative, and preparation method and application thereof
Technical Field
The invention belongs to the fields of synthesis of organic compounds and pesticides, and particularly relates to a 1, 2, 3-triazole sulfonamide derivative, and a preparation method and application thereof.
Background
In the age of continuous variation of organisms, the increase of drug resistance of various microorganisms has prompted the design and development of new drugs. The compounds containing nitrogen and nitrogen-containing heterocyclic rings, which generally contain nitrogen-containing groups such as pyrazole rings and isoxazole rings in their molecular structures, generally have various biological activities such as antibacterial and anticancer drugs. Therefore, modification, synthesis and activity research of nitrogen heterocycle or nitrogen-containing side chain of a compound are important fields.
In recent years, research into developing novel antibacterial agents by a method of linking two different active fragments has been receiving increasing attention from researchers. The drug synthesized by the method has two independent structural parts in the molecule, can be combined with two or more biological targets, and can realize synchronous accumulation at the targets. The dual or multi-action drugs can greatly overcome the drug resistance of the current microorganism or reduce the possibility of occurrence of new drug resistant strains in the process of acting.
The currently used antibacterial agents such as indolmycin, pyrazinamide, isoniazid, fluconazole and other systems with nitrogen-containing heterocycles, i.e. indole, pyrazine, pyridine, triazole and condensed compounds thereof, are attracting attention of researchers due to their remarkable biological activity. 1, 2, 3-triazole in the nitrogen-containing heterocycle has better solubility and affinity with biological targets due to a plurality of unique structural characteristics such as hydrogen bond formation, dipole-dipole action and pi-pi stacking action, has wide pharmacological action, and is a part of structures of antibacterial, antituberculosis drugs, neuraminidase inhibitors, anticancer compounds, antiviral drugs, analgesic and anti-inflammatory compounds, antidiabetic drugs, herbicides and plant growth regulators. The sulfonamide compound has antimicrobial, antitumor, antiinflammatory, blood sugar lowering, antipsychotic, and anticancer effects. Since the first sulfanilamide drug, baiwang's chou, more and more researchers have focused on the development and screening of sulfanilamide drugs. The sulfonamide antibacterial agents are widely used, such as Sulfamethoxazole (SMZ), sulfamethoxazole (SIZ), sulfamidine (SG), sulfadimidine (SM 2), sulfadiazine (SD) and Sulfamethoxypyridazine (SMP). The antibacterial mechanism is to competitively inhibit the synthesis and metabolism of PABA utilized by bacteria to inhibit bacterial growth. The sulfonamide compound and 1, 2, 3-triazole have wide biological activity, the invention synthesizes 1, 2, 3-triazole sulfonamide by taking sulfonamide as a starting raw material, and then introduces common amide bonds with antibacterial active groups, thereby synthesizing a series of 1, 2, 3-triazole benzenesulfonyl compounds. The compound has excellent functions of bacteriostasis, disinsection, sterilization and the like on escherichia coli, pseudomonas aeruginosa, salmonella typhi, staphylococcus aureus, bacillus subtilis, fungi such as candida albicans, aspergillus niger and the like, pests and plant pathogenic bacteria in forestry and other fields.
Disclosure of Invention
Aiming at the problems, the invention aims to provide 1, 2, 3-triazole benzenesulfonyl derivatives, a preparation method and application thereof, and the compounds have excellent antibacterial and insecticidal activities and can be used as pesticides for preventing and treating agricultural diseases. To achieve the above object, the present invention provides the following synthetic routes of 1, 2, 3-triazole benzenesulfonyl group. The synthetic route is as follows:
further, the synthesis method of each step in the above synthesis route is as follows:
1) Sulfonamide is reacted with nitrous acid in hydrochloric acid solution to form diazonium salt which is further reacted with sodium azide to form azide sulfonamide (compound)
2). That is, sulfonamide (0.69 g,4 mmol) was dissolved in a 250mL round bottom flask containing 2mol/L hydrochloric acid and stirred at 0deg.C until completely dissolved. Sodium nitrite (0.35 g,5 mmol) was dissolved in cold water and slowly added to the reaction mixture via a constant pressure funnel. After complete addition, sodium azide (0.325 g,5 mmol) dissolved in a very small amount of water was added to the reaction system, the reaction system was stirred at room temperature, the residue was collected by filtration, washed with deionized water and dried to give product 2 in 92.0% yield.
2) Coupling of the azide sulfonamide with ethyl acetoacetate yields 1, 2, 3-triazole sulfonamide (compound 3). That is, ethyl acetoacetate (0.27 g,2.00 mmol) and piperidine (25. Mu.L) were added to a 150mL round bottom flask containing an appropriate amount of DMSO, and the mixture was heated and stirred for five minutes at 70℃under a silicone oil bath, followed by the addition of Compound 2 (0.40 g,2.00 mmol). After the addition, the reaction mixture was brought to 95℃C
The reaction is stirred for 4 to 6 hours. After the reaction was completed, the mixture was cooled and poured into cold water, and suction filtration was performed to obtain compound 3 in 79.4% yield
3) The 1, 2, 3-triazole sulfonamide directly performs transesterification with an amine compound or reacts with the amine compound after hydrolysis and acyl chlorination. Namely, the compound 3 is hydrolyzed and acidified by hydrochloric acid under alkaline condition to obtain white solid 4. A150 mL three-necked round bottom flask was taken, one end of which was capped with a rubber stopper, the flask was baked with a high temperature spray gun for 5min to remove residual water in the flask, and then the oxygen in the flask was removed with a vacuum pump and a nitrogen ball equipped with a three-way valve and nitrogen protected. Compound 4 (0.29 g,1 mmol) was taken and dissolved in thionyl chloride and added to a round bottom flask through a needle, excess thionyl chloride was added, heated under reflux for 12h, after the reaction was completed, excess thionyl chloride was distilled off under reduced pressure, and repeated rotary evaporation was performed by adding several dichloromethane until the oily liquid was completely converted to a yellow solid, compound 5.
4) Reacting compound 5 with amine compound under alkaline condition such as triethylamine to obtain 1, 2, 3-triazole sulfonamide derivative (compound 6)
Detailed Description
The present invention will be further described in detail with reference to the following examples to better understand the content of the present invention, but the present invention is not limited to the following examples.
Example 1: synthesis of Compound 6a
Aniline (0.047 g,0.5 mmol), triethylamine (0.31 g,3.0 mmol) were taken in a 150mL round bottom flask, an appropriate amount of dioxane was added followed by addition of compound 5 (0.1 g,0.33 mmol), the system was heated under reflux for 1h, after completion of the reaction the mixture was diluted with water, the solid precipitate was filtered off with suction, and washed three times with 0.5mol/L hydrochloric acid, sodium carbonate solution and saturated brine to give a dark brown solid product 6a in 76.0% yield.
1 H NMR(500MHz,DMSO-d 6 )δ10.51(s,1H),8.09–8.05(m,2H),7.94–7.89(m,2H),7.86(d,J＝8.0Hz,2H),7.60(s,2H),7.35(t,J＝7.8Hz,2H),7.11(t,J＝7.4Hz,1H),2.63(s,3H)。
Example 2: synthesis of Compound 6b
O-methylaniline (0.054 g,0.5 mmol), triethylamine (0.31 g,3.00 mmol) were taken in a 150mL round bottom flask, an appropriate amount of dioxane was added followed by addition of compound 5 (0.1 g,0.33 mmol), the system was heated under reflux for 1h, after completion of the reaction the mixture was diluted with water, the solid precipitate was filtered off with suction, and washed three times with 0.5mol/L hydrochloric acid, sodium carbonate solution and saturated brine, respectively, to give a brown solid product 6b, 77.4%.
1 H NMR(500MHz,DMSO-d 6 )δ9.99(s,1H),8.17–8.01(m,2H),7.95–7.85(m,2H),7.60(s,2H),7.51(d,J＝7.9Hz,1H),7.28(d,J＝7.5Hz,1H),7.22(t,J＝7.6Hz,1H),7.15(t,J＝7.4Hz,1H),2.61(s,3H),2.29(s,3H)。
Example 3: synthesis of Compound 6c
Compound 3 (0.1 g,0.33 mmol) was taken and excess ethylenediamine was added to a 150mL round bottom flask containing an appropriate amount of methanol and reacted at 65℃for 5 hours, after the completion of the reaction methanol and excess ethylenediamine were distilled off, a tan solid was obtained, and recrystallization was carried out with ethanol to give product 6c in 92.4% yield.
1 H NMR(500MHz,DMSO-d 6 )δ8.55(t,J＝5.9Hz,1H),8.05(d,J＝8.3Hz,2H),7.87(d,J＝8.3Hz,2H),3.27(d,J＝6.3Hz,2H),2.69(t,J＝6.6Hz,2H),2.57(s,3H),2.53(s,2H)。
Example 4: synthesis of Compound 6d
2, 4-dimethylaniline (0.042 g,0.34 mmol), triethylamine 4 drops and a proper amount of dichloromethane were taken and added into a 150mL round-bottomed flask, compound 5 (0.05 g,0.17 mmol) was slowly added after stirring and mixing, the reaction system was washed three times with 0.5mol/L hydrochloric acid, sodium carbonate solution and saturated brine respectively after completion of the reaction followed by thin layer chromatography, the organic phase was dried over anhydrous sodium sulfate for 3 hours, and then the solvent was distilled off by rotary evaporation to give a pale yellow powdery solid product 6d with a yield of 52.7%.
1 H NMR(400MHz,DMSO-d 6 )δ9.92(s,1H),8.08(d,J＝8.6Hz,2H),7.91(d,J＝8.5Hz,2H),7.61(s,2H),7.36(d,J＝8.0Hz,1H),7.09(d,J＝2.0Hz,1H),7.02(dd,J＝8.1,2.0Hz,1H),2.61(s,3H),2.29(s,3H),2.24(s,3H)。
Example 5: synthesis of Compound 6e
3, 5-dimethylaniline (0.061 g,0.2 mmol), triethylamine 4 drops and a proper amount of methylene chloride were taken and added to a 150mL round-bottomed flask, compound 5 (0.05 g,0.17 mmol) was slowly added after stirring and mixing, and after completion of the reaction by heating and refluxing, the reaction system was washed three times with a 0.5mol/L hydrochloric acid solution, a sodium carbonate solution and saturated brine, respectively, and the organic phase was dried over anhydrous sodium sulfate for 3 hours, followed by rotary evaporation of methylene chloride to give 6e as a yellowish-brown powdery solid in 58.4% yield.
1 H NMR(400MHz,DMSO-d 6 )δ10.36(s,1H),8.14(d,J＝8.6Hz,2H),7.97(d,J＝8.4Hz,2H),7.67(s,2H),7.55(s,2H),6.82(s,1H),2.69(s,3H),2.33(s,6H)。
Example 6: synthesis of Compound 6f
2, 6-dimethylaniline (0.061 g,0.2 mmol), triethylamine 4 drops and a proper amount of methylene chloride were taken and added to a 150mL round-bottomed flask, compound 5 (0.05 g,0.17 mmol) was slowly added after stirring and mixing, and after completion of the reaction by heating and refluxing, the reaction system was washed three times with a hydrochloric acid solution of 0.5mol/L, a sodium carbonate solution and a saturated brine, respectively, and the organic phase was dried over anhydrous sodium sulfate for 3 hours, followed by rotary evaporation of methylene chloride to give a dark yellow powdery solid product 6f in a yield of 64.5%.
1 H NMR(400MHz,DMSO-d 6 )δ10.10(s,1H),8.16–8.11(m,2H),8.01–7.97(m,2H),7.67(s,2H),7.18(s,3H),2.66(s,3H),2.27(s,6H)。
Example 7: synthesis of Compound 6g
Para-fluoroaniline (0.038 g,0.34 mmol), triethylamine 4 drops and a proper amount of dichloromethane were taken and added to a 150mL round-bottomed flask, compound 5 (0.05 g,0.17 mmol) was slowly added after stirring and mixing, and after completion of the reaction by heating and refluxing, the reaction system was washed 3 times with a 0.5mol/L hydrochloric acid solution, a sodium carbonate solution and saturated brine, respectively, and the organic phase was dried over anhydrous sodium sulfate for 3 hours, followed by rotary evaporation of dichloromethane to give 6g of a tan powdery solid product in a yield of 44.7%.
1 H NMR(400MHz,DMSO-d 6 )δ10.70(s,1H),8.16–8.11(m,2H),7.99–7.90(m,4H),7.68(s,2H),7.26(t,J＝8.9Hz,2H),2.71(d,J＝9.3Hz,3H)。
Example 8: synthesis of Compound 6h
P-chloroaniline (0.044 g,0.34 mmol), triethylamine 4 drops and a proper amount of dichloromethane were taken and added to a 150mL round-bottomed flask, compound 5 (0.5 g,0.17 mmol) was slowly added after stirring and mixing, and after completion of the reaction by heating and refluxing, the reaction system was washed with a hydrochloric acid solution of 0.5mol/L, a sodium carbonate solution and saturated brine, respectively, and the organic phase was dried over anhydrous sodium sulfate for 3 hours, followed by rotary evaporation of dichloromethane to give a brown yellow powdery solid product of 6 hours in 48.0% yield.
1 H NMR(400MHz,DMSO-d 6 )δ10.78(s,1H),8.18–8.12(m,2H),8.00–7.95(m,4H),7.68(s,2H),7.47(d,J＝8.7Hz,2H),2.69(s,3H)。
Example 9: synthesis of Compound 6i
Paranitroaniline (0.028 g,0.2 mmol) was added to a 150mL round bottom flask containing an appropriate amount of toluene, 8 drops of triethylamine were added, compound 5 (0.5 g,0.17 mmol) was added after stirring at room temperature for five minutes, the temperature was raised to 120℃for reflux reaction, and after completion of the reaction, the precipitate was filtered off with suction by thin layer chromatography, washed three times with 0.5mol of hydrochloric acid and saturated brine, and then dried in an oven to give a tan product 6i in 62.4% yield.
1 H NMR(400MHz,DMSO-d 6 )δ11.21(s,1H),8.30–8.25(m,2H),8.22–8.17(m,2H),8.12–8.07(m,2H),7.96–7.91(m,2H),7.64(s,2H),2.65(s,3H)。
Example 10: synthesis of Compound 6j
2-nitro-4-methylaniline (0.031 g,0.2 mmol) was added to a 150mL round bottom flask containing an appropriate amount of toluene, 8 drops of triethylamine were added, after stirring at room temperature for five minutes, compound 5 (05 g,0.17 mmol) was added, the temperature was raised to 120℃for reflux reaction, and after completion of the reaction, the precipitate was filtered off with suction by thin layer chromatography, washed three times with 0.5mol of hydrochloric acid and saturated brine, and then dried in an oven to give a tan product 6j in 66.0% yield.
1 H NMR(400MHz,DMSO-d 6 )δ11.42(s,1H),8.23(dd,J＝8.5,3.1Hz,1H),8.07(q,J＝9.0Hz,4H),7.99(s,1H),7.93(d,J＝8.3Hz,1H),7.63(s,2H),2.63(s,3H),2.40(s,3H)。
Example 11: synthesis of Compound 6k
4-aminopyrimidine (0.048 g,0.2 mmol) was taken and added to a 150mL round bottom flask containing an appropriate amount of toluene, 8 drops of triethylamine were added, compound 5 (0.5 g,0.17 mmol) was added after stirring at room temperature for five minutes, the temperature was raised to 120℃for reflux reaction, and after completion of the reaction, the precipitate was filtered off with suction by thin layer chromatography, washed three times with 0.5mol of hydrochloric acid, saturated brine and then dried in an oven to give a tan product 6k in 68.2% yield.
1 H NMR(500MHz,DMSO-d 6 )δ10.35(s,1H),8.80(d,J＝4.9Hz,1H),8.75(d,J＝4.8Hz,1H),8.28(d,J＝5.0Hz,1H),8.01(d,J＝8.5Hz,2H),7.84(d,J＝8.5Hz,2H),2.62(s,3H)。
Example 12: evaluation of bacteriostatic Effect
The in vitro bacteriostatic activity of the synthesized compound is measured by a perforation method. Sulfamethoxazole (SMZ) was used as a positive control for gram-negative and gram-positive bacteria (E.coli, P.aeruginosa, salmonella typhi, staphylococcus aureus, bacillus subtilis); fluconazole (FLUCZ) served as a positive control for fungi (candida albicans, aspergillus niger). The synthesized compound and the two positive drugs were dissolved in DMSO to prepare 512. Mu.g/mL, and then the drugs were diluted with DMSO to 256. Mu.g/mL, 128. Mu.g/mL, 64. Mu.g/mL, 32. Mu.g/mL, 16. Mu.g/mL, 8. Mu.g/mL, 4. Mu.g/mL, 2. Mu.g/mL, and 1. Mu.g/mL, respectively, and the diameters of the inhibition zones of the drugs at the above ten concentrations were measured.The concentration is 1×10 6 CFU/mL of pathogenic bacteria (determined by the turbidimetric method of Maillard) were tested. The solid culture medium is prepared by using TSB which is configured and sterilized, solid culture with the height of about 5mm is injected on the surface of each culture dish, 100 mu L of degerming liquid is beaten on the surface of the solid culture medium by a liquid transferring gun after the solid culture is solidified, and the solid culture medium is uniformly coated. And (3) taking oxford cups from sterilized tweezers to punch holes on a solid culture medium, sucking about 50 mu L of various liquid medicines into the holes by a liquid transferring gun, placing a culture dish into a constant temperature incubator for culturing for 18-25h, adjusting the temperature according to the proper temperature of each strain, taking out the culture dish after the culturing is completed, and measuring the size of a bacteriostasis ring by using a vernier caliper. 1. The antibacterial results of the 2, 3-triazole benzenesulfonyl derivatives are shown in table 1, and the 1, 2, 3-triazole benzenesulfonyl derivatives have better antibacterial effect on various strains.
Table 1Minimuminhibitory concentration of compounds 6a-6k,SMZ，FLUCZ.

Claims (8)

1. 1, 2, 3-triazole sulfonamide derivative is characterized in that the structure is shown as a general formula (A);
in the general formula (A), R is benzene and benzene derivatives, heterocycle and derivatives, C 1 -C 5 Alkanes.
2. The compound of claim 1, wherein R in formula (a) is benzene and its benzene derivatives.
Wherein R is 1 、R 2 、R 3 、R 4 、R 5 Are identical or different and are independently selected from H, halogen, methyl and nitro.
3. The compound of claim 1, wherein R in the general structural formula (a) is pyridine or pyrimidine or a derivative thereof.
4. The compound of claim 1, wherein R in formula (A) is C 1 -C 5 Alkanes.
5. The compound according to claim 1, which is synthesized by the route:
6. the use of the 1, 2, 3-triazole sulfonamide compound according to claim 1 for preparing antibacterial and bactericidal pesticides.
7. The use of claim 6, wherein the insecticide is for killing agronomic pests; the antibacterial agent is used for inhibiting and killing plant pathogenic bacteria.
8. The use according to claim 6, wherein the bacteriostatic agent is for use in medicine.
CN202310979340.2A 2023-08-05 2023-08-05 1, 2, 3-triazole sulfonamide derivative, and preparation method and application thereof Pending CN116947771A (en)

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