CN105820133A - Polysubstituted s-triazine compound and preparation method and application thereof - Google Patents
Polysubstituted s-triazine compound and preparation method and application thereof Download PDFInfo
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- -1 Polysubstituted s-triazine compound Chemical class 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical group C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 3
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 26
- 241000588724 Escherichia coli Species 0.000 abstract description 7
- 238000000338 in vitro Methods 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 4
- 238000002474 experimental method Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940124350 antibacterial drug Drugs 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XJUJXVATKIRSAM-UHFFFAOYSA-N fluoro(phenyl)methanol Chemical compound OC(F)C1=CC=CC=C1 XJUJXVATKIRSAM-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NTTLKRPWPKPUAI-UHFFFAOYSA-N (1e)-1-[amino(anilino)methylidene]-2-phenylguanidine Chemical compound C=1C=CC=CC=1N=C(N)\N=C(/N)NC1=CC=CC=C1 NTTLKRPWPKPUAI-UHFFFAOYSA-N 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229960000723 ampicillin Drugs 0.000 description 2
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 2
- 229960003105 metformin Drugs 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical group 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- 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
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a compound shown in formula (III)The preparation method of the polysubstituted s-triazine compound comprises the following steps: adding an alcohol compound shown in a formula (I), biguanide hydrochloride shown in a formula (II), a metal ruthenium catalyst and an alkaline substance into a solvent, stirring and reacting for 10-18 h at 80-130 ℃, and then carrying out post-treatment on a reaction solution to obtain a polysubstituted s-triazine compound shown in a formula (III); the method has the advantages of mild reaction conditions, easily obtained raw materials, convenient operation, low cost and wide industrial application prospect; preliminary in vitro antibacterial experiment results show that the compound has a certain inhibition effect on escherichia coli, and can be applied to preparation of antibacterial drugs and antibacterial agents.
Description
(1) technical field
The present invention relates to a kind of polysubstituted s-triazine compound and its preparation method and application.
(2) background technology
Compound in triazine class has the multiple biological activitys such as anticancer, malaria, weeding, is widely used in the field such as medicine, pesticide.Wherein, the preparation of s-triazine compound is mainly reacted by cyanoguanidines and nitrile compounds, biguanide is reacted with ester type compound, amide and dimethyl-acetal and amidine or guanidine reaction etc..Research for polysubstituted s-triazine compound and preparation method thereof has important theory significance and actual application value.
(3) summary of the invention
It is an object of the invention to provide a kind of polysubstituted s-triazine compound and its preparation method and application.
The present invention adopts the following technical scheme that
A kind of polysubstituted s-triazine compound shown in formula (III):
In formula (III),
R1For hydrogen or C1～C5 alkyl, preferably hydrogen or methyl；
R2For C1～C5 alkyl or C6～C10 aryl, preferably methyl or phenyl；
R3For hydrogen or C6～C10 aryl, preferably hydrogen or phenyl；
R4For C8～C15 arylalkenyl or C6～C10 halogenated aryl, described C6～C10 halogenated aryl is fluorinated aryl or bromo aryl, preferably styryl, to fluorophenyl or p-bromophenyl.
Present invention also offers the preparation method of polysubstituted s-triazine compound shown in a kind of formula (III), described preparation method is:
Alcohol compound shown in formula (I) is added in solvent with the biguanide hydrochloride shown in formula (II), metal Ru catalyst, alkaline matter, stirring reaction 10～18h at 80～130 DEG C, reactant liquor is post-treated afterwards, obtains the polysubstituted s-triazine compound shown in formula (III)；
Wherein,
R1For hydrogen or C1～C5 alkyl, preferably hydrogen or methyl；
R2For C1～C5 alkyl or C6～C10 aryl, preferably methyl or phenyl；
R3For hydrogen or C6～C10 aryl, preferably hydrogen or phenyl；
R4For C8～C15 arylalkenyl or C6～C10 halogenated aryl, described C6～C10 halogenated aryl is fluorinated aryl or bromo aryl, preferably styryl, to fluorophenyl or p-bromophenyl.
In preparation method of the present invention, the alcohol compound shown in described formula (I) and the biguanide hydrochloride shown in formula (II), metal Ru catalyst, the ratio of amount of material of alkaline matter are 1:0.5～1.5:0.01～0.04:1.0～3.0.
Described solvent is ethers, preferably Isosorbide-5-Nitrae-dioxane.The volumetric usage recommending described solvent is calculated as 10～50mL/g with the quality of the alcohol compound shown in formula (I).
Described metal Ru catalyst is divalent ruthenium compound, preferably 1,5-cyclo-octadiene ruthenous chloride.
Described alkali is organic base, preferably potassium tert-butoxide.
Described post processing can be adopted with the following method: after reaction terminates, add water in reactant liquor 1.0～3.0 times of reactant liquor volume (volumetric usage of usual water be), then it is extracted with ethyl acetate, collected organic layer, it is dried with anhydrous sodium sulfate, filter, concentrated filtrate, gained concentrate carries out column chromatography for separation, with dichloromethane: the methanol volume ratio mixed liquor as 50:1 is as eluant, collect the eluent containing target compound, be dried after removing solvent under reduced pressure, obtain target compound shown in formula (III).
Polysubstituted s-triazine compound of the present invention has certain inhibitory action to escherichia coli, has application prospect in the preparation of antibacterials and antibacterial.
The beneficial effects of the present invention is, this technological reaction mild condition, raw material is easy to get, easy to operate, low cost, has prospects for commercial application widely；Initial in vitro antibacterial experiment result shows, the compounds of this invention has certain inhibitory action to escherichia coli, has corresponding practical value.
(4) detailed description of the invention
Below by specific embodiment, the present invention is further illustrated, but protection scope of the present invention is not limited to that.
Embodiment 1: the preparation of compound (III-1)
In reaction vessel, add 1,5-diphenyl biguanide hydrochloride (0.1653g, 0.9954mmol), to fluoro benzyl alcohol (0.1342g, 1.0642mmol), 1,5-cyclo-octadiene ruthenous chloride (0.0056g, 0.02mmol), potassium tert-butoxide (0.2250g, 2.0052mmol), Isosorbide-5-Nitrae-dioxane (4mL), stirring reaction 15 hours in 100 DEG C of oil baths；After reaction terminates, add water (10mL), is extracted with ethyl acetate (10mL × 3), merges organic layer, it is dried with anhydrous sodium sulfate, filters, concentrated filtrate, gained concentrate carries out column chromatography for separation, and eluant is dichloromethane: methanol=50:1 (V:V), collects RfThe eluent (TLC monitors, the same eluant of developing solvent) of value 0.3～0.35, decompression distillation, it is dried to obtain target compound (III-1) 0.2012g, yield is 55%.
1HNMR(500MHz,CDCl3) δ 8.46 (m, 2H), 7.63 (d, J=7.6Hz, 4H), 7.53 (br, 2H), 7.37 (t, J=7.6Hz, 4H), 7.21 7.09 (m, 4H).
Embodiment 2:
Reaction temperature changes into 80 DEG C, and other operations, with embodiment 1, finally give target compound (III-1) 0.1463g, and yield is 40%.
Embodiment 3:
Reaction temperature changes into 130 DEG C, and other operations, with embodiment 1, finally give target compound (III-1) 0.106g, and yield is 29%.
Embodiment 4:
By 1, the amount of 5-cyclo-octadiene ruthenous chloride changes 0.0115g, 0.04mmol into, and other operations, with embodiment 1, finally give target compound (III-1) 0.1975g, and yield is 54%.
Embodiment 5:
By 1, the amount of 5-cyclo-octadiene ruthenous chloride changes 0.0027g, 0.01mmol into, and other operations, with embodiment 1, finally give target compound (III-1) 0.1609g, and yield is 44%.
Embodiment 6:
Changing the amount of potassium tert-butoxide into 0.3369g, 3.0mmol, other operations, with embodiment 1, finally give target compound (III-1) 0.1829g, and yield is 50%.
Embodiment 7:
Changing the amount of potassium tert-butoxide into 0.1136g, 1.0mmol, other operations, with embodiment 1, finally give target compound (III-1) 0.03658g, and yield is 10%.
Embodiment 8:
To change in the response time 18 hours, other operations, with embodiment 1, finally give target compound (III-1) 0.1829g, and yield is 50%.
Embodiment 9:
To change in the response time 10 hours, other operations, with embodiment 1, finally give target compound (III-1) 0.1280g, and yield is 35%.
Embodiment 10:
Changing the amount of Metformin into 0.2478g, 1.5mmol, other operations, with embodiment 1, finally give target compound (III-1) 0.0915g, and yield is 25%.
Embodiment 11:
Changing the amount of benzylalcohol into 0.1622g, 1.5mmol, other operations, with embodiment 1, finally give target compound (III-1) 0.1793g, and yield is 49%.
Embodiment 12: the preparation of compound (III-2)
Fluoro benzyl alcohol, with embodiment 1, simply will be changed to bromobenzyl alcohol (0.1874g, 0.9977mmol) by operation, prepare target compound (III-2) 0.2276g, and yield is 56%.
1HNMR(500MHz,CDCl3): δ 8.30 (d, J=8.5Hz, 2H), 7.67 (d, J=7.8Hz, 4H), 7.66 7.58 (d, J=8.5Hz, 2H), 7.40 (t, J=7.8Hz, 4H), 7.21 (br, 2H), 7.17 7.10 (m, 2H).
Embodiment 13: the preparation of compound (III-3)
Operation is with embodiment 1, simply fluoro benzyl alcohol will be changed to cinnamyl alcohol (0.1399g, 1.0125mmol), by 1,5-diphenyl biguanide hydrochloride is changed to Metformin (0.1653g, 0.9954mmol), preparing target compound (III-3) 0.0635g, yield is 23%.
1HNMR(500MHz,CDCl3) δ 7.95 (d, J=15.9Hz, 1H), 7.63 7.58 (m, 2H), 7.41 7.31 (m, 3H), 6.85 (d, J=15.9Hz, 1H), 5.23 (s, 2H), 3.26 (s, 3H), 3.15 (s, 3H).
Embodiment 14: the In Vitro Bacteriostatic of escherichia coli (E.coli, Ec) is tested
Diffusion method (punch method) is used to have studied the target compound In Vitro Bacteriostasis when concentration is 10mg/mL to escherichia coli (E.coli, Ec).
Method: make a call to 6 holes with sterilized card punch cruciform symmetry on the plate of coating bacterium solution, be separately added into, with sterile micro syringe, the sample dimethyl sulphoxide solution that 100 μ L mass concentrations are 10mg/mL, and with ampicillin as reference substance.Culture dish is placed in constant temperature (28 DEG C) incubator cultivation 24h, takes out and observe with or without bacteriostasis, the results are shown in Table 1.
Table 1 compound concentration is 10mg/mL antibacterial activity in vitro
| Test No. | Compound | Ec |
| 1 | (III-1) | + |
| 2 | (III-2) | + |
| 3 | (III-3) | ++ |
| Reference substance | Ampicillin | +++ |
Claims (10)
1. the polysubstituted s-triazine compound shown in a formula (III):
In formula (III),
R1For hydrogen or C1～C5 alkyl；
R2For C1～C5 alkyl or C6～C10 aryl；
R3For hydrogen or C6～C10 aryl；
R4For C8～C15 arylalkenyl or C6～C10 halogenated aryl.
Polysubstituted s-triazine compound the most as claimed in claim 1, it is characterised in that described R1For hydrogen or methyl.
Polysubstituted s-triazine compound the most as claimed in claim 1, it is characterised in that described R2For methyl or phenyl.
Polysubstituted s-triazine compound the most as claimed in claim 1, it is characterised in that described R3For hydrogen or phenyl.
Polysubstituted s-triazine compound the most as claimed in claim 1, it is characterised in that described R4For for styryl, to fluorophenyl or p-bromophenyl.
6. a preparation method for polysubstituted s-triazine compound shown in formula as claimed in claim 1 (III), described preparation method is:
Alcohol compound shown in formula (I) is added in solvent with the biguanide hydrochloride shown in formula (II), metal Ru catalyst, alkaline matter, stirring reaction 10～18h at 80～130 DEG C, reactant liquor is post-treated afterwards, obtains the polysubstituted s-triazine compound shown in formula (III)；
Alcohol compound shown in described formula (I) and the biguanide hydrochloride shown in formula (II), metal Ru catalyst, the ratio of amount of material of alkaline matter are 1:0.5～1.5:0.01～0.04:1.0～3.0；
Wherein,
R1For hydrogen or C1～C5 alkyl；
R2For C1～C5 alkyl or C6～C10 aryl；
R3For hydrogen or C6～C10 aryl；
R4For C8～C15 arylalkenyl or C6～C10 halogenated aryl.
7. preparation method as claimed in claim 6, it is characterised in that described solvent is Isosorbide-5-Nitrae-dioxane；The volumetric usage of described solvent is calculated as 10～50mL/g with the quality of the alcohol compound shown in formula (I).
8. preparation method as claimed in claim 6, it is characterised in that described metal Ru catalyst is 1,5-cyclo-octadiene ruthenous chloride.
9. preparation method as claimed in claim 6, it is characterised in that described alkali is potassium tert-butoxide.
The polysubstituted s-triazine compound the most as claimed in claim 1 application in the preparation of antibacterials and antibacterial.
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| CN107033093A (en) * | 2017-06-07 | 2017-08-11 | 浙江工业大学 | N substituted sulphonamide compounds and preparation method and application |
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| CN107129498A (en) * | 2017-03-22 | 2017-09-05 | 浙江工业大学 | Imidazoles arone compounds and preparation method and application |
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