CN109438376A - A kind of bis- heteroaryl substituted triazole compounds of 4,5- and the preparation method and application thereof - Google Patents
A kind of bis- heteroaryl substituted triazole compounds of 4,5- and the preparation method and application thereof Download PDFInfo
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- CN109438376A CN109438376A CN201811508254.9A CN201811508254A CN109438376A CN 109438376 A CN109438376 A CN 109438376A CN 201811508254 A CN201811508254 A CN 201811508254A CN 109438376 A CN109438376 A CN 109438376A
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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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
- Y02A40/22—Improving land use; Improving water use or availability; Controlling erosion
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- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
- Y02P60/20—Reduction of greenhouse gas [GHG] emissions in agriculture, e.g. CO2
- Y02P60/21—Dinitrogen oxide [N2O], e.g. using aquaponics, hydroponics or efficiency measures
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
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Abstract
The present invention relates to 4,5- of one kind, bis- heteroaryl substituted triazole compounds and the preparation method and application thereof, the structure of 4,5-, the bis- heteroaryl substituted triazole compounds is
Description
Technical field
The invention belongs to be catalyzed and organic synthesis field, and in particular to 4,5- of one kind, bis- heteroaryl substituted triazole compounds and
Preparation method and application.
Background technique
Triazole class formation is a kind of important group in bioactive compound, is the weight of numerous chemical industry, medicine intermediate
Want structure.Triazole class compounds medicine, in terms of show multiple biological activities, especially in disinfectant use in agriculture side
Face, the triazole bactericidal agent being commercialized at present existing more than 20.The synthetic methods of triazole class compounds mainly include the following types:
(1) prepared by alkynes and reaction of sodium azide；(2) prepared by benzaldehyde, nitromethane and reaction of sodium azide.The above method is both needed to use
To explosive sodium azide, and severe reaction conditions.Therefore, it is badly in need of developing a kind of without the use of sodium azide preparation triazole type
The method for closing object, the present invention provide a kind of biological carbon load base catalyst for catalyzing and synthesizing 4,5-, bis- heteroaryl substituted triazole
Object is closed, and tests 4, the anti-insect activity of bis- heteroaryl substituted triazole compounds of 5-.
Summary of the invention
Triazole class compounds that bis- heteroaryl of 4,5- that the present invention provides a kind of formula III structure replaces or its can pharmaceutically connect
The salt received, it is characterised in that formula III structure is as follows:
Wherein X is selected from O or S.
Another embodiment of the present invention provides the preparation method of above-mentioned formula III structural compounds, it is characterised in that including
Following steps:
Compound of formula I and anhydrous hydrazine, in dehydrated alcohol reflux temperature react 3-4 hour after, be added Formula II compound with
Biological carbon loads alkali, continues back flow reaction 4-5 hours to get formula III compound；Wherein X is selected from O or S.
Compound of formula I, anhydrous hydrazine, Formula II compound molar ratio be 1:1.3-1.5:1.0-1.2；Biological carbon loads alkali
Dosage is that every mM of compound of formula I uses 15-20mg biological carbon load alkali.
The preparation method of the biological carbon load alkali includes the following steps:
(1) it takes ginkgo leaf, clean, after drying to constant weight, in N2In the presence of, 800 are risen to the heating rate of 10 DEG C/min
DEG C, after heat preservation carbonization 3 hours, it is down to room temperature and obtains biological carbon；
(2) biological carbon for obtaining step (1) is with after dipping by lye 12 hours, washing, be drying to obtain biological carbon load alkali.
Lye described in step (2) is selected from the aqueous solution of alkali metal hydroxide, concentration 4-6mol/L；The alkali gold
Belong to one or more of the preferred sodium hydroxide of hydroxide, potassium hydroxide, cesium hydroxide.The dosage of lye is can sufficiently impregnate
It is advisable, it is preferable to use 10-15mL lye for every gram of biological carbon.
Another embodiment of the present invention provides 4,5- of one kind, bis- furans -2- base -2H-1, the preparation method of 2,3- triazoles,
It is characterized by comprising following steps:
2 furan carboxyaldehyde is dissolved in dehydrated alcohol, anhydrous hydrazine is added, after being heated to reflux temperature reaction 3-4 hours, is added
Enter 2- cyanofuran and above-mentioned biological carbon load alkali, continue back flow reaction 4-5 hours to get 4,5-, bis- furans -2- base -2H-1,
2,3- triazole.
2 furan carboxyaldehyde, anhydrous hydrazine, 2- cyanofuran molar ratio be 1:1.3-1.5:1.0-1.2；Biological carbon loads alkali
Dosage be that every mM of compound of formula I using 15-20mg biological carbon loads alkali.
Another embodiment of the present invention provide above-mentioned formula III compound or its pharmaceutically acceptable salt prepare it is pest-resistant
Application in active medicine.It is preferred that preparing the application in bollworm resisting drug.
Another embodiment of the present invention provides a kind of pharmaceutical composition, it is characterised in that with above-mentioned formula III compound or
Its pharmaceutically acceptable salt is as effective component.Its may also include pharmaceutically acceptable auxiliary material (such as carrier, diluent,
Excipient etc.).
Compared with the prior art, the advantages of the present invention are as follows: (1) it is of the invention by obtain a kind of biological carbon load alkali,
It can be used for being catalyzed benzaldehyde (or 2- heteroaryl carboxaldehyde), anhydrous hydrazine and benzonitrile (or 2- cyanofuran or the 2- cyanogen optionally replaced
Base thiophene) synthesis the disubstituted triazole class compounds of 4,5- catalyst, provide new think of for the synthesis of triazole class compounds
Road is avoided using explosive azide；(2) bis- heteroaryl substituted triazole compounds of 4,5- prepared by the present invention are in bollworm resisting
Aspect shows significant activity, is better than 4,5- diphenyl substituted triazole compounds.
Detailed description of the invention
Fig. 1 is the SEM figure of product A；
Fig. 2 is the HRMS figure of embodiment 3.
Specific embodiment
For the ease of a further understanding of the present invention, examples provided below has done more detailed description to it.But
It is that these embodiments are only not supposed to be a limitation to the present invention or implementation principle for better understanding invention, reality of the invention
The mode of applying is not limited to the following contents.
The preparation of 1 biological carbon of embodiment load alkali
(1) it takes ginkgo leaf (200g), clean, after drying to constant weight, in N2In the presence of, with the heating rate liter of 10 DEG C/min
To 800 DEG C, after heat preservation carbonization 3 hours, it is down to room temperature and obtains biological carbon；
(2) biological carbon (10g) for taking step (1) to obtain is impregnated 12 hours with sodium hydroxide solution (6mol/L, 100mL)
Afterwards, it washes, be drying to obtain biological carbon load alkali (hereinafter referred to as product A, Fig. 1).
Embodiment 2
The biological carbon (10g) that 1 step of Example (1) obtains is small with potassium hydroxide solution (4mol/L, 150mL) immersion 12
Shi Hou is washed, is drying to obtain biological carbon load alkali (hereinafter referred to as product B, consistent with Fig. 1).
The preparation of 3 4,5- diphenyl -2H-1,2,3- triazole of embodiment
Benzaldehyde (2mmol) is dissolved in dehydrated alcohol (20mL), is added anhydrous hydrazine (2.4mmol), reflux temperature is heated to
After degree reaction 6 hours, benzonitrile (1.6mmol) and product A (20mg) is added, after continuing back flow reaction 5 hours, production is recovered by filtration
Product A is diluted with chloroform and is successively washed with water, saturated sodium-chloride after filtrate concentration, and anhydrous sodium sulfate is dried, filtered, is concentrated,
Through silica gel column chromatography (200-300 mesh silica gel), uses petrol ether/ethyl acetate (15:1-10:1) as eluant, eluent, it is solid to obtain white
Body 329mg, as 4,5- diphenyl -2H-1,2,3- triazole compounds, yield about 92.9%.1H NMR(CDCl3,400MHz),
δ: 12.82 (br s, 1H), 7.54 (d, J=3.3Hz, 4H), 7.38-7.36 (m, 6H)13C NMR(CDCl3,100MHz),δ:
142.8,130.4,128.7,128.6,128.3.HRMS (such as Fig. 2).
The preparation of 4 4- of embodiment (3- bromophenyl) -5- phenyl -2H-1,2,3- triazole
3-bromobenzaldehyde (1.0mmol) is dissolved in dehydrated alcohol (15mL), is added anhydrous hydrazine (1.5mmol), is heated to
After reflux temperature reacts 5 hours, benzonitrile (1.0mmol) and product B (15mg) is added, after continuing back flow reaction 4 hours, filtering
It recycles product B to be diluted with chloroform and successively washed with water, saturated sodium-chloride after filtrate concentration, anhydrous sodium sulfate is dry, mistake
Filter, concentration, through silica gel column chromatography (200-300 mesh silica gel), use petrol ether/ethyl acetate (15:1-10:1) as eluant, eluent, obtain
To solid 268mg, as 4- (3- bromophenyl) -5- phenyl -2H-1,2,3- triazoles, yield about 89.3%.1H NMR(CDCl3,
400MHz),δ:7.76(s,1H),7.55-7.39(m,4H),7.36-7.34(m,3H),7.20-7.17(m,1H).13C NMR
(CDCl3,100MHz),δ:132.3,131.6,131.1 130.2,129.2.HRMS Calcd(ESI)m/z for
C14H10BrN3:[M+H]+300.0131,found:300.0125,[M+2+H]+302.0111,found:302.0106.
The preparation of 5 4,5- of embodiment, bis- furans -2- base -2H-1,2,3- triazole
2 furan carboxyaldehyde (2mmol) is dissolved in dehydrated alcohol (20mL), is added anhydrous hydrazine (2.6mmol), is heated to back
2- cyanofuran (2.0mmol) and product A (30mg) is added after thermotonus 4 hours in stream, after continuing back flow reaction 5 hours, mistake
Filter recycling product A is diluted with chloroform and is successively washed with water, saturated sodium-chloride after filtrate concentration, and anhydrous sodium sulfate is dry, mistake
Filter, concentration, through silica gel column chromatography (200-300 mesh silica gel), use petrol ether/ethyl acetate (10:1-8:1) as eluant, eluent, obtain
To solid 336mg, bis- furans -2- base -2H-1 of as 4,5-, 2,3- triazoles, yield about 83.5%.1H NMR(CDCl3,
400MHz),δ:7.45-7.33(m,2H),7.25-7.14(m,4H).13C NMR(CDCl3,100MHz),δ:144.5,142.9,
140.6,136.2,128.4.HRMS Calcd(ESI)m/z for C10H7N3O2:[M+H]+202.0611,found:
202.0584.
The preparation of 6 4,5- Dithiophene -2- base -2H-1,2,3- triazole of embodiment
2 thiophene carboxaldehyde (1mmol) is dissolved in dehydrated alcohol (15mL), is added anhydrous hydrazine (1.5mmol), is heated to back
2- cyano thiophene (1.2mmol) and product B (20mg) is added after thermotonus 3 hours in stream, after continuing back flow reaction 5 hours, mistake
Filter recycling product B is diluted with chloroform and is successively washed with water, saturated sodium-chloride after filtrate concentration, and anhydrous sodium sulfate is dry, mistake
Filter, concentration, through silica gel column chromatography (200-300 mesh silica gel), use petrol ether/ethyl acetate (10:1-8:1) as eluant, eluent, obtain
To solid 192mg, as 4,5- Dithiophene -2- base -2H-1,2,3- triazoles, yield about 82.3%.1H NMR(CDCl3,
400MHz),δ:7.29-7.25(m,2H),7.05-6.98(m,4H).13C NMR(CDCl3,100MHz),δ:138.9,131.8,
129.5,128.4.HRMS Calcd(ESI)m/z for C10H7N3S2:[M+H]+234.0154,found:234.0147.
Embodiment 7
2 furan carboxyaldehyde (2mmol) is dissolved in dehydrated alcohol (20mL), is added anhydrous hydrazine (2.6mmol), is heated to back
Stream is added 2- cyanofuran (2.0mmol) after thermotonus 4 hours, and after continuing back flow reaction 5 hours, TLC detection is found no
Bis- furans -2- base -2H-1,2,3- triazole of 4,5- generates.
Embodiment 8
2 furan carboxyaldehyde (1mmol) is dissolved in dehydrated alcohol (10mL), is added anhydrous hydrazine (1.3mmol), is heated to back
Stream is added 2- cyanofuran (1.0mmol) and product A (embodiment 5 recycles, 15mg), continues to flow back after thermotonus 4 hours
After reaction 5 hours, product A is recovered by filtration, after filtrate concentration, is diluted and is successively washed with water, saturated sodium-chloride, nothing with chloroform
Aqueous sodium persulfate is dried, filtered, is concentrated, through silica gel column chromatography (200-300 mesh silica gel), with petrol ether/ethyl acetate (10:1-8:
1) it is used as eluant, eluent, obtains solid 163mg, yield about 81.1%, structural identification data is same as Example 5.
9 bollworm resisting active testing of embodiment
Using the wooden chinaberry element as positive control drug, the compounds of this invention: 4,5- diphenyl -2H-1,2,3- triazoles, 4- (3- is tested
Bromophenyl) -5- phenyl -2H-1,2,3- triazole, bis- furans -2- base -2H-1,2,3- triazole of 4,5-, 4,5- Dithiophene -2- base -
Anti-insect activity of the 2H-1,2,3- triazole to bollworm.As a result as follows:
| Test compound | IC50(μg/mL) |
| 4,5- diphenyl -2H-1,2,3- triazole | >100 |
| 4- (3- bromophenyl) -5- phenyl -2H-1,2,3- triazole | >100 |
| Bis- furans -2- base -2H-1,2,3- triazole of 4,5- | 50 |
| 4,5- Dithiophene -2- base -2H-1,2,3- triazole | 50 |
| The wooden chinaberry element | 25 |
Claims (10)
1. triazole class compounds or its pharmaceutically acceptable salt that a kind of 4,5-, bis- heteroaryl of formula III structure replaces, special
Sign is that formula III structure is as follows:
Wherein X is selected from O or S.
2. the preparation method of formula III structural compounds described in claim 1, it is characterised in that include the following steps:
After reflux temperature reacts 3-4 hours in dehydrated alcohol, Formula II compound and biology is added in compound of formula I and anhydrous hydrazine
Carbon loads alkali, continues back flow reaction 4-5 hours to get formula III compound；Wherein X is selected from O or S.
3. preparation method as claimed in claim 2, it is characterised in that compound of formula I, anhydrous hydrazine, Formula II compound molar ratio be
1:1.3-1.5:1.0-1.2；The dosage of biological carbon load alkali is that every mM of compound of formula I is loaded using 15-20mg biological carbon
Alkali.
4. the described in any item preparation methods of claim 2-3, it is characterised in that the preparation method packet of the biological carbon load alkali
Include following steps:
(1) it takes ginkgo leaf, clean, after drying to constant weight, in N2In the presence of, 800 DEG C are risen to the heating rate of 10 DEG C/min, is protected
After temperature carbonization 3 hours, it is down to room temperature and obtains biological carbon；
(2) biological carbon for obtaining step (1) is with after dipping by lye 12 hours, washing, be drying to obtain biological carbon load alkali.
5. preparation method as claimed in claim 4, it is characterised in that lye described in step (2) is selected from alkali metal hydroxide
Aqueous solution, concentration 4-6mol/L.
6. preparation method described in claim 5, it is characterised in that the preferred sodium hydroxide of the alkali metal hydroxide, hydroxide
One or more of potassium, cesium hydroxide.
7. formula III compound described in claim 1 or its pharmaceutically acceptable salt answering in preparation anti-insect activity drug
With.
8. application as claimed in claim 7, it is characterised in that preferably preparing the application in bollworm resisting drug.
9. a kind of pharmaceutical composition, it is characterised in that with formula III compound described in claim 1 or its is pharmaceutically acceptable
Salt is as effective component.
10. pharmaceutical composition as claimed in claim 9, it is characterised in that its may also include pharmaceutically acceptable auxiliary material (such as
Carrier, diluent, excipient etc.).
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101755801A (en) * | 2010-01-25 | 2010-06-30 | 中国农业大学 | Purpose of substituent phenyl furaldehyde thiosemicarbazone compound as insect tyrosinase inhibitor |
| CN102246825A (en) * | 2011-05-11 | 2011-11-23 | 王乃利 | Biopesticide and preparation method thereof |
| CN108794412A (en) * | 2018-09-10 | 2018-11-13 | 海南师范大学 | A kind of preparation method of 4,5- diaryl -2H-1,2,3- triazole compounds |
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2018
- 2018-12-10 CN CN201811508254.9A patent/CN109438376B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101755801A (en) * | 2010-01-25 | 2010-06-30 | 中国农业大学 | Purpose of substituent phenyl furaldehyde thiosemicarbazone compound as insect tyrosinase inhibitor |
| CN102246825A (en) * | 2011-05-11 | 2011-11-23 | 王乃利 | Biopesticide and preparation method thereof |
| CN108794412A (en) * | 2018-09-10 | 2018-11-13 | 海南师范大学 | A kind of preparation method of 4,5- diaryl -2H-1,2,3- triazole compounds |
Non-Patent Citations (2)
| Title |
|---|
| SUBHANKAR PANDA ET AL.,: ""Transition Metal, Azide, and Oxidant-Free Homo- and Heterocoupling of Ambiphilic Tosylhydrazones to the Regioselective Triazoles and Pyrazoles"", 《ORG. LETT.》 * |
| 李东风: "《有机化学》", 31 August 2007 * |
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