CN100334084C - Bi-triazole compound, preparation method and application thereof - Google Patents
Bi-triazole compound, preparation method and application thereof Download PDFInfo
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Abstract
The present invention relates to a bi-triazole compound whose general formula is disclosed in a figure, wherein R stands for carboethoxymethyl, p-amyl phenyl, cyclohexanol, cyclohexenyl or p-methoxyphenyl. A preparation method of the compound comprises the following steps: 5-triazo-1, 2, 4 triazol-3-acyl methyl ester reacts with propiolic alcohol ester acetate, p-amyl phenylacetylene, syclohexanol alkyne, cyclohexene alkyne or methoxyphenyl acetylene in tetrahydrofuran or mixed solvent of tetrahydrofuran and water with the catalysis of Cu(I) and at the temperature of 40 to 100 DEG C, which leads the required bi-triazole compound to be obtained. The preparation of the bi-triazole compound prepared according to the present invention is simple, and the price is low. The bi-triazole compound can be used for directly inhibiting the activity of plant viruses and especially inhibiting the activity of tobacco mosaic viruses. Therefore, the bi-triazole compound can be used as an inhibiting agent of plant viruses and especaially as an inhibiting agent of tobacco mosaic viruses. The bi-triazole compound can be used as a primer of medicine for resisting viruses.
Description
Technical field
The present invention relates to bi-triazole compound and its production and use, belong to organic chemistry and biochemical field.
Background technology
The viroses of plant have the title of " plant cancer ", and ratio shared in Plant diseases is only second to fungal disease, causes serious threat to agriculture production, relevant research (Whitham, 2004) in the ascendant.Only (Tobacco mosaic virus, the loss that TMV) causes just reaches more than 100,000,000 dollars by tobacco mosaic virus (TMV) every year in the whole world according to estimates.Because virus obligatory parasitism in vegetable cell, it duplicates required material, energy and place and relies on the host fully, and plant do not have complete immune metabolic system, makes the control difficulty particularly of the viroses of plant.In order to prevent and treat the viroses of plant effectively, people have carried out good try to many schemes, as utilize the generation of agricultural measures (crop rotation, rotate crops, select for use resistant variety and seed detoxification treatment etc.) prevention virus disease; Utilize the cross protection between virus to select for use biotechnological formulations such as low virulent strain system and satellite RNA to come dip-dye and the propagation of viral interference; Especially the transgenic plant of antiviral gene provide new approach (Li Zaiguo etc., 1999) for the mankind conquer virus disease; In addition, the communication media by sterilant control virus also is used to prevent and treat the popular of virus disease.Yet these measures are to use separately or integrated application all can not overcome the harm that virus disease causes effectively.
In order to develop ideal Antiphytoviral medicament, the chemical science worker has carried out the synthetic and screening trial of many orientations.In recent decades, in study on prevention, develop two big class antiviral agents both at home and abroad to plant virus: the one, crude substance such as microorganism, mushroom and plant milk extract, the 2nd, synthetic chemical substance.The former representative have Japan at first the NS83 of Lentemin, China exploitation of exploitation and Ningnanmycin and antofine etc. (to Gu Xi etc., 1995; Hu Houzhi etc., 1998; An etc., 2001; Yao Yucheng etc. 2001).This class medicament mainly is that protective plant is not subjected to virus infection, and some also can passivation virus, and their antiviral spectrum are narrower.The representative of synthetic medicament has virazole (Ribavirin), hydrogenation s-triazine diketone (DHT) and E30, and octicin solution, moroxydine hydrochloride and the triacontanol price quote etc. of China's exploitation.These medicaments have preventive and therapeutic effect concurrently to virus disease.Their can passivation virus, also can suppress the propagation with viral interference, though their antiviral spectrum broad is limited after all, and the land for growing field crops preventive effect that they comprise natural goods is generally between 30%～60%, obviously this is not enough.Up to now, we also do not develop the similarly efficient or ultra-high efficiency of picture sterilant and weedicide and sterilant etc. and eco-friendly medicament.
In the process of the discovery of agricultural chemicals guide thing and optimization, combinatorial chemistry has played very big effect in recent years.The advantage of combinatorial chemistry is to synthesize quickly and efficiently and can be used for the compound testing or screen in a large number.Yet because the input of a large amount of compounds, combinatorial chemistry also more depends on each than traditional synthetic chemistry and independently reacts, and is reacted by these and to make up new chemical bond network.And click chemistry (Click Chemistry) is a kind of method that more can promote this synthetic process, and this method has been used some and has been close to perfect chemical reactions and synthesizes and assemble new structural unit.By using these most convenients and chemical conversion process the most selectively, click chemistry has been simplified the synthetic of compound, and the method that finds the medicine guide fast and optimize product is provided.The appearance of click chemistry is not to replace already present classical way in the drug discovery, but will replenish and extend these methods.Simultaneously, the appearance of " click chemistry " notion just can realize that to using reaction seldom the diversity of compound has directive significance.A click chemistry reacts mandatory principle and is: reaction is carried out easily, and insensitive to the oxygen G﹠W, reaction raw materials is easy to get, and the processing of reaction separates with product must be simple.By the Huisgen 1 of nitrine and alkynes generation 1,2,3-triazoles, the 3-Dipolar Cycloaddition is a most typical click chemistry reaction just.The characteristics of this reaction are the reliability of its height, the biocompatibility of specificity and reactant completely.And the triazole compounds of gained usually can be by dipolar interaction or hydrogen bond and acts on mutually with a lot of biological targets, thereby becomes a potential active structure unit.
At present, people are many as research antiviral, antitumor, antifungal agents to triazole derivative.Most typical representative is exactly virazole (Ribavirin) to triazole compounds as antiviral agent, and it also is one of medicament of present Antiphytoviral preferably (comprising animal) of generally acknowledging.People have obtained a series of derivative by virazole is modified.CN 1420723, and the triazole derivative of CN 85108679 and CN1063183 report is exactly the analogue of virazole, and this compounds has antiviral preferably and antitumous effect usually.In some external nearest patents relevant report is arranged also, just reported the triazole compounds that some are used for the treatment of cell disease and have anticancer effect as WO 2004037809, WO02088108, AU 2003256003.
More than Bao Dao compound only contains a triazole unit usually.It is then less relatively to introduce two unitary reports of triazole in compound.CN 1259867 has reported a kind of pharmaceutical composition that can suppress the growth of tumour and cancer in the Mammals, and it comprises mycocide.Used concrete mycocide is 1,3-pair-triazolyl-2-propanol derivative.These compositions infect also effective to animal virus.FI 893051 has also reported the compound of similar structures in the external patent, and its concrete structure is as follows:
R wherein
1Be the alkyl that replaces arbitrarily, cycloalkyl (as, cyclopentyl or cyclohexyl), aryl or halogenated aryl (as phenyl or 2,4 dichloro benzene base) or aralkyl (as benzyl).
CN 1195288 has reported a kind of pharmaceutical composition for the treatment of mammalian cancer or tumour, wherein comprises 2-(2,4 difluorobenzene base)-1, two (1H-1,2,4-triazol-1-yl) propan-2-ol and the derivatives thereof of 3-.Can with certain chemotherapeutics the same with synergistic agent with 2-(2,4 difluorobenzene base)-1, two (1H-1,2,4-triazol-1-yl) propan-2-ols of 3-and derivative thereof share.2-(2,4 difluorobenzene base)-1, two (1H-1,2,4-triazol-1-yl) propan-2-ols of 3-and derivative thereof can also be used for the treatment of animal virus to be infected, and perhaps uses separately, perhaps share with other antiviral and synergistic agent.Its concrete structure is as follows:
EP 113509-A, two triazole compounds of US 4466974 reports are used for the treatment of by fungus-caused part or system to infect, and are the effectively antifungal compounds of a class.Its concrete structure formula is as follows:
R
1Can be single replacement, two replacement or polysubstituted phenyl, substituted radical comprises F, Cl, Br, I, CF
3, 1-4C alkyl, 1-4C alkoxyl group or 5-chloro-2-pyridyl etc.; X is NH
2, single or disubstituted (1-4C alkyl) amino, or NHCOOR '; R ' is the 1-4C alkyl.
In addition, the azole compounds that structure is following also is a kind of unitary compound of two triazole structures of having introduced, and SU 1643538-A1 once had report among SU 1622368-A and the SU 1622368.But this compounds is often used in measuring in the spectrophotometry some element or as the selectivity brightener, yet there are no report as antiviral or antifungal drug.Its structural formula is as follows:
R is NO
2Or NH
2
The triazole compounds of above patent report does not all relate to the structural unit that is directly linked to each other by two triazole ring, is not applied to the research of Antiphytoviral yet.Therefore, we to utilize in the click chemistry most widely used Huisgen cycloaddition reaction to come a series of bi-triazole compounds of synthetic are the novel structural units of a class.Because tobacco mosaic virus (TMV) is a kind of important model of agricultural plants virus research, so this patent utilizes tobacco mosaic virus (TMV) that the synthetic compound has been carried out preliminary screening, test-results shows that this compounds has the better prevention effect to tobacco mosaic virus (TMV).And our synthetic bi-triazole compound suppresses tobacco mosaic virus (TMV) under similarity condition activity is better than commercial Antiphytoviral reagent-virazole.Simultaneously, except commercial Anti-virus agent, the inhibitor of the resisting tobacco mosaic virus of bibliographical information is the product that known structural unit with anti-phytoviral activity is carried out derivatize mostly, as benzothiazoles, benzimidazoles, DHT class, pyridazinone, pyranone, quinazoline compounds etc.And this patent synthetic bi-triazole compound yet there are no report.Wherein, compound 1d shows the outstanding preventive and therapeutic effect to tobacco mosaic virus (TMV) in preliminary screening, and the Antiphytoviral medicament of developing new class for us provides the guide.And compare with the loaded down with trivial details synthetic route of above-mentioned multiclass compound, the synthetic method that this patent provides is simple, inexpensive, environmental friendliness, has broad application prospects
Summary of the invention
Problem to be solved by this invention provides class bi-triazole compound and its production and use, the gained bi-triazole compound not only prepares simpler, inexpensive, and can suppress the activity of plant mosaic virus, can be used for being subjected to the therapeutical agent of mosaic virus invasion and attack plant.
Technical scheme provided by the invention is: bi-triazole compound, and its general formula is:
Wherein R be ethyl ester methyl (1a), to amyl group phenyl (1b), hexamethylene alcohol radical (1c), cyclohexenyl (1d) and p-methoxyphenyl (1e).
The preparation method of above-claimed cpd, react by Huisgen, with 5-azido--1,2,4 triazoles-3-acyl methyl esters and acetate propine alcohol ester, to amylbenzene acetylene, hexalin alkynes, hexamethylene eneyne or anisole acetylene in the mixed solvent of tetrahydrofuran (THF) or tetrahydrofuran (THF) and water, 40-100 ℃ of reaction obtains required bi-triazole compound under Cu (I) catalysis.
The consumption mol ratio of above-mentioned 5-azido--1,2,4-triazoles-3-acyl methyl esters and alkynes is 1: 1-1.5.
Above-mentioned 5-azido--1,2,4-triazoles-3-acyl methyl esters is that the concentration of solvent is the 0.01-1 mol with tetrahydrofuran (THF) or tetrahydrofuran (THF) and water.
The consumption volume ratio of the mixed solvent of above-mentioned tetrahydrofuran (THF) and water is 1: 1-4.
Above-mentioned bi-triazole compound is as the application of viroses of plant inhibitor.
Above-mentioned bi-triazole compound is as the application of tobacco mosaic virus (TMV) inhibitor.
The bi-triazole compound that the present invention makes not only prepares simple, inexpensive, and can directly suppress the especially activity of tobacco mosaic virus (TMV) of plant virus, thereby can be used as the especially inhibitor of tobacco mosaic virus (TMV) of plant virus, as guide's thing of antiviral.
Description of drawings
Accompanying drawing is the design sketch of The compounds of this invention 1d resisting tobacco mosaic virus.
Embodiment
By the following examples the present invention is further described.
Embodiment one:
(50mg 0.297mmol) places two-mouth bottle, adds 10mL mixed solvent (THF/H after handling 20 minutes vacuumizing on the oil pump with 5-azido--1,2,4-triazoles-3-acyl methyl esters
2O=1/4), obtain water white solution.Under the Ar gas shiled, add again acetate propine alcohol ester (35mg, 0.36mmol).In addition with cupric sulfate pentahydrate (11.8mg, 0.047mmol) and SODIUM ASCORBATE (29.5mg, 0.148mmol) be dissolved in the 200 μ L water respectively after, the above-mentioned reaction system of reinjecting.Be reflected at 80 ℃ the reaction 1 hour after, stopped reaction, this moment reaction system be yellow turbid solution, remove solvent under reduced pressure after, obtain yellow solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=30/1), the product that obtains (1a) is white solid 73.1mg, productive rate 92.4% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ8.79(s，1H)，5.22(s，2H)，3.96(s，3H)，2.07(s，3H)；
13CNMR(150MHz，DMSO-d
6)：δ171.2，158.1，144.0，125.1，57.7，54.1，21.5；ESI-MS：m/z 264.9[M-H]
-.
Embodiment two
(50mg 0.297mmol) places two-mouth bottle, adds mixed solvent 5mL (THF/H after handling 20 minutes vacuumizing on the oil pump with 5-azido--1,2,4-triazoles-3-acyl methyl esters
2O=1/2), material dissolution obtains water white solution.Under the Ar gas shiled, add again to the pentane phenylacetylene (50mg, 0.297mmol).In addition with cupric sulfate pentahydrate (11.8mg, 0.047mmol) and SODIUM ASCORBATE (29.5mg, 0.148mmol) be dissolved in the 200 μ L water respectively after, the above-mentioned reaction system of reinjecting.Be reflected at 60 ℃ the reaction 2 hours after, stopped reaction, this moment reaction system be pale brown look turbid solution, directly remove solvent under reduced pressure after, obtain pale brown look solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=30/1), the product that obtains (1b) is white solid 82.2mg, productive rate 81.2% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ9.24(s，1H)，7.88(d，2H，J＝7.8Hz)，7.27(d，2H，J＝7.8Hz)，3.93(s，3H)，2.57(t，2H，J＝7.8Hz)，1.56(m，2H)，1.25(m，4H)，0.83(t，3H，J＝6.4Hz)；
13CNMR(150MHz，DMSO-d
6)：δ159.3，155.4，150.2，147.5，143.3，129.5，128.0，126.2，120.6，53.0，35.6，31.5，31.2，22.6，14.6；ESI-MS：m/z 339.0[M-H]
-.
Embodiment three
(50mg 0.297mmol) places two-mouth bottle, adds tetrahydrofuran (THF) 12mL after handling 20 minutes vacuumizing on the oil pump, and material dissolution obtains water white solution with 5-azido--1,2,4-triazoles-3-acyl methyl esters.Under the Ar gas shiled, add again hexalin alkynes (54.7mg, 0.44mmol).In addition with cupric sulfate pentahydrate (11.8mg, 0.047mmol) and SODIUM ASCORBATE (29.5mg, 0.148mmol) be dissolved in the 200 μ L water respectively after, the above-mentioned reaction system of reinjecting.Be reflected at 90 ℃ the reaction 2 hours after, stopped reaction, this moment reaction system be faint yellow turbid solution, directly remove solvent under reduced pressure after, obtain yellow solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=30/1), the product that obtains (1c) is white solid 67.5mg, productive rate 77.7% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ8.41(s，1H)，5.07(br s，1H)，3.93(s，3H)，1.89-1.96(m，2H)，1.66-1.77(m，3H)，1.42-1.50(m，3H)，1.21-1.30(m，2H)；
13C NMR(150MHz，DMSO-d
6)：δ157.9，157.2，121.0，68.6，53.7，38.2，25.8，22.3；ESI-MS：m/z 291.1[M-H]
-.
Embodiment four:
(50mg 0.297mmol) places two-mouth bottle, adds mixed solvent 9mL (THF/H after handling 20 minutes vacuumizing on the oil pump with 5-azido--1,2,4-triazoles-3-acyl methyl esters
2O=1/2), material dissolution obtains water white solution.Under the Ar gas shiled, add again the hexamethylene eneyne (38.6mg, 0.36mmol).In addition with cupric sulfate pentahydrate (11.8mg, 0.047mmol) and SODIUM ASCORBATE (29.5mg, 0.148mmol) be dissolved in the 200 μ L water respectively after, the above-mentioned reaction system of reinjecting.Be reflected at 80 ℃ the reaction 4 hours after, stopped reaction, this moment reaction system be yellow turbid solution, directly remove solvent under reduced pressure after, obtain yellow solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=30/1), the product that obtains (1d) is white solid 72.3mg, productive rate 88.7% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ8.69(s，1H)，6.58(s，1H)，3.91(s，3H)，2.35(m，2H)，2.14(m，2H)，1.67(m，2H)，1.59(m，2H)；
13C NMR(150MHz，DMSO-d
6)：δ160.1，155.7，151.2，148.8，127.6，125.3，119.3，52.6，26.4，25.4，22.7，22.5；ESI-MS：m/z 273.1[M-H]
-.
Embodiment five:
(50mg 0.297mmol) places two-mouth bottle, adds mixed solvent 9mL (THF/H after handling 20 minutes vacuumizing on the oil pump with 5-azido--1,2,4-triazoles-3-acyl methyl esters
2O=1/2), material dissolution obtains water white solution.Under the Ar gas shiled, add again to anisole acetylene (47.2mg, 0.36mmol).In addition with cupric sulfate pentahydrate (11.8mg, 0.047mmol) and SODIUM ASCORBATE (29.5mg, 0.148mmol) be dissolved in the 200 μ L water respectively after, the above-mentioned reaction system of reinjecting.Be reflected at 80 ℃ the reaction 2.5 hours after, stopped reaction, this moment reaction system be faint yellow turbid solution, directly remove solvent under reduced pressure after, obtain yellow solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=30/1), the product that obtains (1e) is white solid 73.6mg, productive rate 82.5% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ9.22(s，1H)，7.93(d，2H，J＝8.7Hz)，7.03(d，2H，J＝8.7Hz)，3.95(s，3H)，3.79(s，3H)；
13C NMR(150MHz，DMSO-d
6)：δ160.2，157.8，147.7，127.8，122.8，120.1，115.1，55.9，53.7；FAB-MS：m/z 301.0[M+H]
+.
Embodiment six
The active mensuration of the anti-TMV of compound (the withered spot method of half leaf)
On the tobacco plant of the coral of 5～6 leaf ages west, choose the blade (leaf normal, anosis no worm) that is applicable to test, first blade is evenly sprinkled fine emery powder, with writing brush with standby malicious source (3.0 * 10
-3) evenly be put on the blade that spreads powder emery, after treating that the blade that selects in all connects the poison end, immediately with handling 20 minutes in the culture dish that fills the soup that has The compounds of this invention, take out, the globule and soup on the drop defoliation sheet restore two and half leaves to be emitted in the enamel tray that is covered with the toilet paper insulation and add cover glass, 23 ± 2 ℃ of controlled temperature, be placed on the greenhouse natural lighting and get final product, can manifest withered spot in 2～3 days.Each processing all has its corresponding half leaf in contrast, and the processing that one group of commodity virus of A also is set in addition as a comparison.
X: relative effect (%); CK: be soaked in the withered spot number (individual) that half sheet in the clear water connects malicious leaf;
T: the withered spot number (individual) that is dipped in half sheet leaf in the soup
Embodiment seven
The active mensuration of the anti-TMV of compound (live body revulsion)
The screening method of new compound evoking tobacco live body activity of resisting tobacco mosaic virus: the method with reference to (2005) such as model will gold is carried out, common cigarette seedling with the seedling age unanimity, 3 basins are one group, the chemicals treatment mode comprises: the solution 2 to 3 times that sprays The compounds of this invention, each 10mL, or root irrigation cigarette seedling 2 to 3 times, each 20mL, behind the certain hour on tobacco leaf frictional inoculation TMV, after cultivating 3d, check incidence, comprehensive scab number is calculated as follows out the inducing anti-disease toxic effect fruit of The compounds of this invention to TMV, 3 repetitions are established in each processing, and contrast divides blank and standard chemicals treatment to contrast 2 kinds; The effect of inducing of test compounds is divided into 5 grades: A, B, C, D and E, and concrete data are the A level: induce effect＞90%, for excellent; B level: induce effect 90～70%, for very; C level: induce effect 70～50%, for better; D level: induce effect 50～30%, for poor; E level: induce effect＜30% to be considered as not having and induce effect.
What wherein, R was medicament or The compounds of this invention to the anti-TMV of tobacco induces (or live body) effect, unit: %
CK is the average withered spot number of clear water contrast blade, unit: individual
I is the average withered spot number through medicament or The compounds of this invention processing (or inducing processing) rear blade, unit: individual
The bi-triazole compound of the invention described above gained has been carried out the screening of 500 μ g/mL according to the normal experiment that screens, experimental result (seeing the following form) shows, the bi-triazole compound of gained of the present invention has certain inhibition effect to tobacco mosaic virus (TMV), compound 1d particularly, its inhibiting rate (is being seen accompanying drawing) more than 70%, is a very potential tobacco mosaic virus (TMV) inhibitor.The plant inducing anti-disease activator diazosulfide of standard itself does not have the activity of anti-TMV, but it can produce lasting to TMV and resistance that lag behind by evoking tobacco, and by comparison, compound 1d does not but have the inductive activity.
| Compound | Concentration Mg/mL | The effect % of direct anti-TMV virus | The active % of the anti-TMV of evoking tobacco | |
| Foliar spray | Soil treatment | |||
| 1a | 500 | 35 | - | - |
| 1b | 500 | 23 | - | - |
| 1c | 500 | 17 | - | - |
| 1d | 500 | 70，75，72 | 0 | 0 |
| 1e | 500 | 15 | - | - |
| Virazole | 500 | 30 | - | - |
| Diazosulfide | 100 | 0 | 85 | 96 |
Claims (6)
1. bi-triazole compound, its general formula is:
Wherein R be the ethyl ester methyl, to amyl group phenyl, hexamethylene alcohol radical, cyclohexenyl or p-methoxyphenyl.
2. the preparation method of the described bi-triazole compound of claim 1, react by Hui sgen, with 5-azido--1,2,4-triazole-3-acyl methyl esters and acetate propine alcohol ester, to amylbenzene acetylene, hexalin alkynes, hexamethylene eneyne or anisole acetylene in the mixed solvent of tetrahydrofuran (THF) or tetrahydrofuran (THF) and water, 40-100 ℃ of reaction obtains required bi-triazole compound under Cu (I) catalysis.
3. preparation method according to claim 2 is characterized in that: 5-azido--1,2, the consumption mol ratio of 4-triazole-3-acyl methyl esters and alkynes is 1: 1-1.5.
4. according to claim 2 or 3 described preparation methods, it is characterized in that: 5-azido--1,2,4-triazole-3-acyl methyl esters are that the concentration of solvent is the 0.01-1 mol with tetrahydrofuran (THF) or tetrahydrofuran (THF) and water.
5. according to claim 2 or 3 described preparation methods, it is characterized in that: the consumption volume ratio of the mixed solvent of tetrahydrofuran (THF) and water is 1: 1-4.
6. the described bi-triazole compound of claim 1 is as the application of tobacco mosaic virus (TMV) inhibitor.
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| 杂环类植物抗病毒剂的研究进展 张华等，农药，第41卷第2期 2002 * |
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