CN108017618B - Novel compound pyrazole aldehyde pyridine amine Schiff base and preparation method and application thereof - Google Patents
Novel compound pyrazole aldehyde pyridine amine Schiff base and preparation method and application thereof Download PDFInfo
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- 239000002262 Schiff base Substances 0.000 title claims abstract description 43
- -1 compound pyrazole aldehyde pyridine amine Schiff base Chemical class 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 20
- 150000004753 Schiff bases Chemical class 0.000 abstract description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 230000003078 antioxidant effect Effects 0.000 abstract description 6
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000012043 crude product Substances 0.000 abstract description 4
- 238000010992 reflux Methods 0.000 abstract description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ICFGFAUMBISMLR-UHFFFAOYSA-N 1h-pyrazole-5-carbaldehyde Chemical compound O=CC=1C=CNN=1 ICFGFAUMBISMLR-UHFFFAOYSA-N 0.000 description 2
- DKZPJLZXLKAMDO-UHFFFAOYSA-N 5-chloro-3-methyl-1-phenylpyrazole-4-carbaldehyde Chemical compound ClC1=C(C=O)C(C)=NN1C1=CC=CC=C1 DKZPJLZXLKAMDO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- YXFAOWYMDGUFIQ-UHFFFAOYSA-N 2-methoxypyridin-3-amine Chemical compound COC1=NC=CC=C1N YXFAOWYMDGUFIQ-UHFFFAOYSA-N 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention discloses a novel compound pyrazole aldehyde pyridine amine Schiff base, a preparation method and application thereof, wherein the structural formula of the novel compound pyrazole aldehyde pyridine amine Schiff base is as follows:
wherein R is H or OCH3(ii) a Carrying out reflux reaction on 5-chloro-3-methyl-1-phenyl-4-pyrazole formaldehyde and pyridylamine in an ethanol solution for 5-6h according to the molar mass ratio of 1:1.2, then carrying out desolventization to obtain a crude product, and recrystallizing the crude product with ethanol to obtain pyrazole aldehyde pyridylamine Schiff base. The Schiff base has good fluorescence property and certain antioxidant activity, and has potential application value in the aspects of fluorescent materials and antioxidants.
Description
Technical Field
The invention relates to a novel compound pyrazole aldehyde pyridine amine Schiff base and a preparation method and application thereof.
Background
In recent years, heterocyclic chemistry has been a major component of organic chemistry. In the present organic compounds, the amount of heterocyclic compounds is about one third of the total. And nitrogen-containing heterocyclic compounds are an important branch in heterocyclic compounds. The nitrogen-containing heterocyclic compounds and derivatives thereof are increasingly used as intermediates for medicines, pesticides, dyes and other fine chemical products. In particular, the research of pyridine heterocycle and pyrazole heterocycle is favored by the researchers.
Schiff bases are a class of organic compounds containing C ═ N groups, generally formed by the aldehyde or ketone condensation reaction of amines with carbonyl compounds. The Schiff base with rich and variable structure can be synthesized by the transformation of amine groups and the transformation of carbonyl compound groups, and the Schiff base has the characteristics of relative easiness in synthesis, high yield and few byproducts. In recent years, schiff bases have better biological activity and pharmaceutical activity, enzyme-like catalysis, photoelectric property and fluorescence property, such as antibacterial, anticancer, antioxidant, antiviral and the like, so that the schiff bases are more and more emphasized by researchers.
Since the first schiff base was synthesized in 1963, the synthesis and bioactivity research of schiff bases and derivatives thereof show a rapid growth trend. However, Schiff bases formed by pyrazole aldehyde are only reported, and Schiff base compounds formed by condensing pyrazole aldehyde and pyridylamine and biological activity studies thereof are not reported.
Disclosure of Invention
The purpose of the invention is: the novel pyrazole aldehyde pyridine amine Schiff base compound is high in purity, simple in preparation method and easy to industrialize; the Schiff base has good fluorescence property, has certain antioxidant activity, and has potential application value in the aspects of fluorescent materials and antioxidants.
The technical solution of the invention is as follows: the structural formula of the novel compound pyrazole aldehyde pyridine amine Schiff base is as follows:
wherein R is H or OCH3。
The preparation method of the novel compound pyrazole aldehyde pyridine amine Schiff base comprises the following steps: dissolving 5-chloro-3-methyl-1-phenyl-4-pyrazole formaldehyde and substituted pyridylamine in a molar ratio of 1:1.2 by using absolute ethyl alcohol, heating for reflux reaction, monitoring the reaction process by TLC, and finishing the reaction for 5-6 hours; desolventizing the reaction solution by using a rotary evaporator to obtain a crude product; recrystallizing the crude product by using absolute ethyl alcohol to obtain pyrazole aldehyde pyridine amine Schiff base; wherein the structural formula of the substituted pyridylamine is shown in the specification
Wherein R is H or OCH 3.
The Schiff base is prepared into 10 in absolute ethyl alcohol-5The mol/L solution is tested for fluorescence performance at normal temperature and has good fluorescence property.
The application of the Schiff base in oxidation resistance is tested by a DPPH method.
The invention has the advantages that: 1. the traditional heating process is adopted, the reaction operation is simple, and the reaction yield is high; 2. no catalyst is needed to be added, the synthesis step is simple, and the product is easy to purify; 3. the pyrazole aldehyde pyridine amine Schiff base synthesized by the method has good fluorescence property and excellent oxidation resistance.
Drawings
FIG. 1 shows a preparation method of pyrazole aldehyde pyridine amine Schiff base1H NMR spectrum.
FIG. 2 shows the preparation of pyrazole aldehyde pyridine amine Schiff base13C NMR spectrum.
FIG. 3 is a fluorescence spectrum of pyrazole aldehyde pyridine amine Schiff base.
FIG. 4 is a free radical scavenging curve of pyrazole aldehyde pyridylamine Schiff base.
Detailed Description
The present invention will be described in further detail with reference to examples.
EXAMPLE 1 preparation of 5-chloro-3-methyl-1-phenyl-4-pyrazole carboxaldehyde 3-aminopyridine Schiff base
1.10g (5mmo1) of 5-chloro-3-methyl-1-phenyl-4-pyrazolecarboxaldehyde and 0.56g (6mmo 1) of 3-aminopyridine dissolved in 20mL of absolute ethanol were added into a 100mL three-necked flask, and the mixture was heated, refluxed, monitored by TLC, and reacted for 6 hours; removing the solvent by using a rotary evaporator to separate out a solid; the solid is recrystallized by absolute ethyl alcohol, filtered and dried to obtain 1.15g of white solid, namely 5-chloro-3-methyl-1-phenyl-4-pyrazole formaldehyde condensation 3-aminopyridine Schiff base. Yield: 78 percent; melting point: 112 ℃ and 113 ℃.
1H NMR(400Hz,CDCl3,δ/ppm):8.47(s,1H，CH＝N),8.47(d,3JH-H＝1.2Hz,1H,5-H on pyridine),8.44(s,1H，α-H on pyridine),7.26-7.58(m,7H,Hon benzene and pyridine),2.65(s,3H,CH3)；
13C NMR(100Hz,CDCl3,δ/ppm):153.21,150.80,148.53,146.86,142.68,137.58,130.51,129.17,128.72,127.62,125.04,123.59,115.58,14.65。
EXAMPLE 2 preparation of 5-chloro-3-methyl-1-phenyl-4-pyrazole carboxaldehyde 2-methoxy-3-aminopyridine Schiff base
1.10g (5mmo1) of 5-chloro-3-methyl-1-phenyl-4-pyrazolecarboxaldehyde and 0.74g (6mmo 1) of 2-methoxy-3-aminopyridine dissolved in 20mL of absolute ethanol were added into a 100mL three-necked flask, and the mixture was heated, refluxed, monitored by TLC for reaction, and reacted for 5 hours; removing the solvent by using a rotary evaporator to separate out a solid; the solid is recrystallized by absolute ethyl alcohol, filtered and dried to obtain 1.32g of light yellow solid, namely 5-chloro-3-methyl-1-phenyl-4-pyrazole formaldehyde condensation 2-methoxy-3-aminopyridine Schiff base. Yield: 81 percent; melting point: 127 ℃ and 128 ℃.
1H NMR(400Hz,CDCl3,δ/ppm):8.49(s,1H，CH＝N),8.01(d,3JH-H＝4Hz,1H,5-H on pyridine),6.90-7.57(m,7H,H on benzene and pyridine),4.02(s,3H,OCH3),2.65(s,3H,CH3)；
13C NMR(100Hz,CDCl3,δ/ppm):156.92,154.01,150.84,143.12,137.63,136.83,130.20,129.16,128.65,128.0,125.06,117.12,115.84,53.68,14.63。
Test example: at 10-5Testing the fluorescence spectrum of the pyrazole aldehyde pyridine amine Schiff base at room temperature at the mol/L concentration; in FIG. 3, R ═ H and R ═ OCH3When the compound is used, the pyrazole aldehyde pyridine amine Schiff base has a strong fluorescence spectrum at about 500 nm.
Test example: determination of antioxidant activity of pyrazole aldehyde pyridine amine Schiff base by DPPH method
The DPPH method: DPP H is a very stable free radical with nitrogen as the center, the ethanol solution of the DPP H has a maximum absorption peak at 517nm, and if Schiff base can remove the DPP H, the Schiff base has the effects of reducing free radicals such as hydroxyl and breaking the lipid peroxide chain reaction; the DPP H method has been widely used in the screening work of free radical scavengers.
The experimental method comprises the following steps: mixing 0.2mL of sample solutions with 3.8mL of 6.35X10-6Uniformly mixing mol/L DPP H ethanol solution, placing the mixture in a dark place for reaction for 30min, taking absolute ethyl alcohol as reference, measuring the absorbance at 517nm, calculating the clearance rate K of the DPP H removed by the mixture,
K＝[(A0-As)/A0]*100％，
in the formula, A. Absorbance at 517nm for DPP H ethanol solution, AsThe absorbance at 517nm after the samples with different concentrations react with DPP H solution for 30min is cleanedPlotting the removal rate to the solution concentration to obtain a curve of the removal rate of Schiff base to DPPH free radicals, wherein the result is shown in figure 4; as can be seen from the attached figure 4, the pyrazole aldehyde pyridine amine Schiff base has a certain removal effect on hydroxyl radicals at different concentrations, and shows a certain antioxidant activity; but the Schiff base concentration has no obvious influence on the magnitude of the antioxidant activity, has stable scavenging effect on hydroxyl free radicals, and has potential application value in the field of antioxidants.
The above are only preferred embodiments and test examples of the present invention, and are not intended to limit the present invention, and it is obvious that those skilled in the art can make various changes and modifications to the present invention without departing from the spirit and scope of the present invention. It is intended that all such modifications and variations fall within the scope of the invention, which is defined by the claims and their equivalents.
Claims (3)
1. The novel compound pyrazole aldehyde pyridine amine Schiff base is characterized by having the following structural formula:
r ═ H or OCH3。
2. The use of the novel compound pyrazole aldehyde pyridine amine schiff base as claimed in claim 1 in fluorescent materials.
3. The use of the novel compound pyrazole aldehyde pyridine amine schiff base as claimed in claim 1 for preparing antioxidants.
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| CN113105433B (en) * | 2021-04-07 | 2022-05-31 | 淮阴师范学院 | Heterocyclic compound containing pyrazole ring and quinoline ring and preparation method and application thereof |
| CN113549004B (en) * | 2021-06-28 | 2023-09-08 | 淮阴师范学院 | 1-pyrene formaldehyde condensed 3-amino-9-ethyl carbazole Schiff base compound as well as preparation method and application thereof |
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| Title |
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| 《二芳基吡唑类衍生物合成及生物活性评价》;邢曼;《南京大学硕士论文》;20140527;第14页 * |
| 2-氨甲基吡啶缩5-溴水杨酸席夫碱配合物的合成、表征与抗氧化作用;解庆范等;《化学研究》;20150131;第26卷(第1期);35-38页 * |
| Green synthesis of novel pyrazole containing schiff base derivatives as antibacterials on the bases of in-vitro and DFT;Salman等;《European Journal of Chemistry》;20131231;第4卷(第4期);第454-458页 * |
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