CN113105433A - Heterocyclic compound containing pyrazole ring and quinoline ring, preparation method and application thereof - Google Patents
Heterocyclic compound containing pyrazole ring and quinoline ring, preparation method and application thereof Download PDFInfo
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- CN113105433A CN113105433A CN202110371181.9A CN202110371181A CN113105433A CN 113105433 A CN113105433 A CN 113105433A CN 202110371181 A CN202110371181 A CN 202110371181A CN 113105433 A CN113105433 A CN 113105433A
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- heterocyclic compound
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- pyrazole
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 125000003226 pyrazolyl group Chemical group 0.000 title abstract description 16
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract description 10
- -1 DPPH free radical Chemical class 0.000 claims abstract description 20
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 230000003078 antioxidant effect Effects 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000012544 monitoring process Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 2
- ICFGFAUMBISMLR-UHFFFAOYSA-N 1h-pyrazole-5-carbaldehyde Chemical compound O=CC=1C=CNN=1 ICFGFAUMBISMLR-UHFFFAOYSA-N 0.000 abstract description 3
- 150000005010 aminoquinolines Chemical class 0.000 abstract description 2
- 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 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- UNSLQFMTPYHZDA-UHFFFAOYSA-N 2-methylquinolin-5-amine Chemical compound NC1=CC=CC2=NC(C)=CC=C21 UNSLQFMTPYHZDA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229940123457 Free radical scavenger Drugs 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 238000003889 chemical engineering Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XMIAFAKRAAMSGX-UHFFFAOYSA-N quinolin-5-amine Chemical compound C1=CC=C2C(N)=CC=CC2=N1 XMIAFAKRAAMSGX-UHFFFAOYSA-N 0.000 description 3
- 239000002516 radical scavenger Substances 0.000 description 3
- OCZVHBZNPVABKX-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine;ethanol Chemical compound CCO.[O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 OCZVHBZNPVABKX-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000007760 free radical scavenging Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000004949 mass spectrometry Methods 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
- 239000000575 pesticide Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000004792 oxidative damage Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Images
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The invention discloses a heterocyclic compound which is generated by condensing pyrazole aldehyde and aminoquinoline and contains a pyrazole ring and a quinoline ring, and a preparation method and application thereof. The heterocyclic compounds have good DPPH free radical resisting activity and have potential application value in the aspect of preparing antioxidants.
Description
Technical Field
The invention relates to the field of chemical engineering and pharmaceutical chemistry, in particular to a heterocyclic compound which is generated by condensation reaction of 5-chloro-3-methyl-1-phenyl-4-pyrazole formaldehyde and 5-aminoquinoline or 2-methyl-5-aminoquinoline and contains pyrazole ring and quinoline ring, a preparation method thereof and application thereof in the fields of chemical engineering and medicine.
Background
The free radicals are products of human metabolism and show strong oxidation reaction capability in vivo. Excessive free radicals cause oxidative damage to proteins, nucleic acids, lipids, etc. in the human body, thereby causing various diseases such as atheroma, neurodegeneration, chronic depression, cancer and physiological aging]. The antioxidant has the function of eliminating free radicals, and the search for the antioxidant which is efficient, nontoxic and safe is an important research direction in the aspect of free radical biology. There are various methods for screening substances for antioxidant activity, among which DPPH (1, 1-diphenyl-2-trinitrophenylhydrazine) method has good stability, high sensitivity and simple operationAnd the like, and is widely used for quantitative analysis of the free radical scavenging capacity. The method for searching the antioxidant substance mainly comprises two approaches, one is to extract the antioxidant substance from the natural plant body, which is a hot spot for searching the antioxidant at present; the other is artificially synthesized antioxidant substance. At present, most of the widely used antioxidants are artificial chemical synthetic products and are widely applied to health care products, cosmetics and food additives. The search for compounds with simple synthesis, stable structure, excellent performance and low toxicity in environment is a long pursuit of organic synthesizers.
The pyrazole compounds are important heterocyclic compounds and have important application in various fields, in particular to the fields of pesticides and chemical industry. Due to the characteristics of the structure, substituent groups on the pyrazole ring can be transformed into different compounds in multiple directions, so that the pyrazole ring has wide application in the fields of medicines, dyes, conductive reagents, antioxidant activity and the like.
The quinoline compound is a six-membered fused heterocyclic compound containing nitrogen atoms in the structure, and belongs to one of aromatic compounds. In the structure of the compound, after a quinoline ring is introduced, some excellent biological activity and pharmacological activity are often shown, so that the quinoline compound and the derivative thereof are widely applied to the fields of fine chemical engineering, pesticides, medicines, materials and the like.
Based on the theory and the current situation analysis, the invention adopts an active substructure splicing method to splice a pyrazole heterocycle and a quinoline ring into one molecule through simple condensation reaction, so as to synthesize a heterocyclic compound containing both the pyrazole ring and the quinoline ring, and after retrieval, the structure of the heterocyclic compound is not reported in related documents, and the DPPH free radical resistance of the heterocyclic compound is researched.
Disclosure of Invention
The invention provides a heterocyclic compound with a structural formula (I), which has the following structure:
preferably, R ═ H or CH3
Preferably, the heterocyclic compound of formula (I) has the structural formula:
the preparation method of the heterocyclic compound with the general formula (I) comprises the following steps:
(1) dissolving an aminoquinoline compound of formula (III) with a solvent;
(2) adding 5-chloro-3-methyl-1-phenyl-4-pyrazole formaldehyde shown in the formula (II) and aminoquinoline compound solution shown in the formula (III) into a reaction device, heating and refluxing, and reacting for 4.5-6 h;
(3) cooling, concentrating, filtering and washing to obtain a target compound;
preferably, the solvent in step (1) is selected from: n, N-dimethylformamide, dichloromethane, ethanol, isopropanol, tert-butanol, acetonitrile or acetone; more preferably, the solvent is selected from: and (3) ethanol.
Preferably, the amount ratio of (II) 5-chloro-3-methyl-1-phenyl-4-pyrazolecarboxaldehyde and (III) 5-aminoquinoline or 2-methyl-5-aminoquinoline substance in step (2) is 1: 1.
Preferably, the step (2) further comprises monitoring the reaction progress by TLC.
Preferably, the washing step (3) is performed with ethanol.
In a particular embodiment of the invention, the reflux time used is 4.5h or 6 h.
The invention also provides a free radical scavenger which comprises a heterocyclic compound with the structural formula (I).
The invention provides a novel heterocyclic compound containing pyrazole rings and quinoline rings, a preparation method and application thereof, and the heterocyclic compound is simple in preparation method and easy to industrialize; the performance test shows that the novel heterocyclic compound containing pyrazole rings and quinoline rings provided by the invention has good free radical scavenging activity and potential application value in the aspects of free radical scavengers and anti-aging drugs.
Drawings
FIG. 1 shows pyrazole ring and quinoline ring heterocyclic compound R ═ CH3Process for preparing compounds1H NMR spectrum.
FIG. 2 shows pyrazole ring and quinoline ring heterocyclic compound R ═ CH3Process for preparing compounds13C NMR spectrum.
FIG. 3 shows a pyrazole ring and a quinoline ring heterocyclic compound R ═ CH3MS spectrum of compound.
FIG. 4 shows pyrazole ring and quinoline ring heterocyclic compound R ═ H1H NMR spectrum.
FIG. 5 shows pyrazole ring and quinoline ring heterocyclic compound R ═ H13C NMR spectrum.
Fig. 6 is an MS spectrum of a pyrazole ring and quinoline ring heterocyclic compound R ═ H compound.
FIG. 7 is a graph showing radical scavenging rates of heterocyclic compounds containing pyrazole rings and quinoline rings.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only some embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
EXAMPLE 15 preparation of chloro-3-methyl-1-phenyl-4-pyrazole carboxaldehyde 5-aminoquinoline heterocyclic compound
In a 100mL three-necked flask, 0.22g (1mmo1) of 5-chloro-3-methyl-1-phenyl-4-pyrazolecarboxaldehyde and 0.14g (1mmo1) of 5-aminoquinoline dissolved in 20mL of anhydrous ethanol were charged, heated, refluxed, followed by TLC for 6 hours. Cooling, concentrating and separating out solid; the solid is washed by absolute ethyl alcohol for many times, filtered and dried to obtain 0.25g of light yellow powdery solid, namely the 5-chloro-3-methyl-1-phenyl-4-pyrazole formaldehyde-condensed 5-aminoquinoline heterocyclic compound. Yield: 72 percent; melting point: 146 ℃ and 147 ℃.
1H NMR(400Hz，CDCl3，δ/ppm)：8.97(s，1H，CH＝N)，7.16-8.96(m，11H，H on benzenes and quinoline)，2.77(s，3H，CH3)；
13C NMR(100Hz,CDCl3，δ/ppm)：152.23，150.85，149.66，148.69，137.61，132.60，130.48，129.59，129.21，128.74，126.99，125.06，124.41，120.85，115.99，112.70，14.97；
Mass spectrometry data: MS (M/z), 347.9, [ M +1 [)]+。
EXAMPLE 25 preparation of chloro-3-methyl-1-phenyl-4-pyrazole carboxaldehyde 2-methyl-5-aminoquinoline heterocyclic compound
In a 100mL three-necked flask, 0.22g (1mmo1) of 5-chloro-3-methyl-1-phenyl-4-pyrazolecarboxaldehyde and 0.16g (1mmo1) of 2-methyl-5-aminoquinoline dissolved in 20mL of anhydrous ethanol were charged, heated, refluxed, followed by TLC for 4.5 hours. Cooling, concentrating and separating out solid; the solid is washed by absolute ethyl alcohol for a plurality of times, filtered and dried to obtain 0.28g of earthy yellow needle-shaped solid, namely the 5-chloro-3-methyl-1-phenyl-4-pyrazole formaldehyde-condensed 2-methyl 5-aminoquinoline heterocyclic compound. Yield: 78 percent; melting point: 178 ℃ and 179 ℃.
1H NMR(400Hz，CDCl3，δ/ppm)：8.62(s，1H，CH＝N)，7.09-8.59(m，10H，H on benzenes and quinoline)，2.77(s，3H，CH3),2.76(s，3H，CH3)；
13C NMR(100Hz,CDCl3，δ/ppm)：159.41,152.04,150.80,149.52,148.32,137.63,132.68,130.39,129.54,129.19,128.71,126.24,125.05,122.52,121.72,116.01,25.38,14.94。
Mass spectrometry data: MS (M/z), 362.1, [ M +1 ]]+。
EXAMPLE 3 measurement of antioxidant Activity of pyrazole aldehyde-condensed aminoquinoline heterocyclic Compound
The antioxidant activity of the pyrazole aldehyde condensed amino quinoline heterocyclic compound is measured by a DPPH method.
The DPPH method: DPPH is a very stable free radical with nitrogen as the center, the ethanol solution of DPPH has the maximum absorption peak at 517nm, if Schiff base can remove it, the Schiff base has the functions of reducing free radicals such as hydroxyl and breaking the lipid peroxidation chain reaction; the DPPH 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 DPPH ethanol solution, placing in dark for reaction for 30min, measuring absorbance at 517nm with anhydrous ethanol as reference, calculating DPPH removal rate K,
K＝[(A0-As)/A0]*100％，
A0the absorbance of the DPPH ethanol solution at 517nm, the absorbance of As at 517nm after the samples with different concentrations react with the DPPH solution for 30min, and the clearance rate is plotted against the solution concentration to obtain a curve of the clearance rate of the heterocyclic compound to DPPH free radicals, wherein the result is shown in figure 7. As shown in the attached figure 7, the heterocyclic compound generated by condensing the pyrazole aldehyde and the aminoquinoline has a certain scavenging effect on hydroxyl free radicals at different concentrations, and shows a certain antioxidant activity; along with the increase of the concentration, the antioxidant activity is obviously enhanced, and the clearance rates of the two compounds are up to more than 36% at the concentration of 0.10g/L, so that the antioxidant has potential application value in the field of antioxidant preparation.
Claims (7)
1. A heterocyclic compound characterized by its structural formula (I):
2. The heterocyclic compound according to claim 1, characterized by the structural formula:
3. the process for producing the heterocyclic compound according to claim 1, which comprises:
(1) dissolving an aminoquinoline compound of formula (III) with a solvent;
(2) adding 5-chloro-3-methyl-1-phenyl-4-pyrazole formaldehyde shown in the formula (II) and aminoquinoline compound solution shown in the formula (III) into a reaction device, heating and refluxing, and reacting for 4.5-6 h;
(3) cooling, concentrating, filtering and washing to obtain the target compound.
4. The method for preparing a heterocyclic compound according to claim 3, characterized in that the solvent in the step (1) is selected from the group consisting of: n, N-dimethylformamide, dichloromethane, ethanol, isopropanol, tert-butanol, acetonitrile or acetone.
5. The method for preparing a heterocyclic compound according to claim 3, characterized in that the step (2) further comprises monitoring the progress of the reaction by TLC.
6. The method for producing a heterocyclic compound according to claim 3, characterized in that the ratio of the amounts of the starting material II to the starting material III is 1:1 to 1.6.
7. The novel heterocyclic compound according to claim 1, characterized in that: the application in the preparation of antioxidant.
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