CN103755840A - Synanthrin derivative containing 1,2,3-triazole and preparation method thereof - Google Patents
Synanthrin derivative containing 1,2,3-triazole and preparation method thereof Download PDFInfo
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Abstract
The invention relates to the agricultural field and the medicine industry, and particularly relates to a synanthrin derivative containing 1,2,3-triazole. A structural formula of the derivative is shown in the formula (1), wherein R is H or Cl, Cl is located in a 2, 3 or 4 position, and the average range of the degree of polymerization is 10-35. A preparation method comprises the steps of: through controlling reaction conditions of temperature, reactant ratio, time and the like, firstly, reacting benzoic acid or chlorinated benzoyl chloride with propargyl alcohol to obtain benzoic acid or chlorobenzoate propargyl ester, reacting with azido acetylated inulin to obtain benzoic acid alkyne or chlorobenzoate propargyl ester-1,2,3-triazole acetylized synanthrin derivative. The reaction is simple and convenient to operate, high in efficiency and easy to popularize; and required equipment and raw materials are easily available. The synanthrin derivative prepared in the invention has good amphipathy, and is enhanced in bioactivity of synanthrin, so that the synanthrin without a remarkable bacteriostasis activity generates a certain bacteriostasis activity, so that the application range of the synanthrin is increased and the synanthrin can be widely applied to the fields such as medicine and agriculture. The formula is described in the specification.
Description
Technical field
The present invention relates to agriculture field and pharmaceutical industries, specifically a kind of synanthrin derivative containing 1,2,3-triazole and preparation method thereof.
Background technology
Synanthrin (Inulin) is called again inulin, is a kind of biological polyoses.By D-fructofuranose molecule, with β-(2,1) glycosidic link, connected and generate, each synanthrin molecule end connects a glucosyl residue with α-(1,2) glycosidic link, and the polymerization degree is generally 2～60, and mean polymerisation degree is 10.
Synanthrin is widespread in nature in some microorganisms and fungus body, but is mainly present in plant materials, and as jerusalem artichoke, witloof, salsify, Garden Dahlia stem tuber etc., wherein jerusalem artichoke is the main raw material source that synanthrin is produced.Jerusalem artichoke is commonly called as Jerusalem artichoke, Jerusalem artichoke, originates in North America, is per nnial herb, and China generally cultivates various places, and its stem tuber is rich in synanthrin, and total synanthrin content is generally 14～l7%, and source is abundant, and cost is lower.In recent years, synanthrin is applied to the field of food such as milk-product, bread, candy, beverage and food flavouring mainly as natural food ingredients.For synanthrin, carry out chemical modification and be applied to agriculture field and the research of pharmaceutical industries rarely has report.
Nitrogen-containing heterocycle compound is because its selectivity is good, activity is high, consumption is few, toxicity is low and specificity in the biochemical physiological response of nuisance becomes the focus of pesticide research.Many efficient Insecticides (tech) & Herbicides (tech)s, sterilant are all nitrogen-containing heterocycle compounds.Wherein triazole class compounds is exactly a very representational class nitrogen heterocyclic ring sterilant.Triazole bactericidal agent has the features such as fungicidal spectrum is wide, activity is high, sterilization speed is fast, the lasting period is long, interior suction conduction is strong, and its development at agriculture field and application are very swift and violent, have become the sterilant of usage quantity maximum at present.To the long-term abuse of this series bactericidal agent, cause the problems such as disease and pest resistance and drug residue day by day serious.Therefore, resistance and the drug injury problem of minimizing triazole bactericidal agent are important directions of pesticide research.
Summary of the invention
The object of the present invention is to provide a kind of synanthrin derivative containing 1,2,3-triazole and preparation method thereof.
For achieving the above object, the technical solution adopted in the present invention is:
A kind of synanthrin derivative containing 1,2,3-triazole and preparation method thereof, derivant structure formula as the formula (1),
In formula (1), R is H or Cl, and wherein Cl is positioned at 2,3 or 4;
The average span of polymerization degree n is 10-35.
A kind of synanthrin derivative containing 1,2,3-triazole and preparation method thereof,
Benzoyl chloride and propargyl alcohol, in trichloromethane, are added to triethylamine, under condition of ice bath, react 1-2h, then back flow reaction 2-3h, obtains phenylformic acid alkynes propyl ester derivative; Phenylformic acid alkynes propyl ester derivative again with nitrine for acetylize synanthrin, under the catalysis of xitix and copper sulfate, under 60-80 ℃ of condition, react 12-24h, obtain a kind of synanthrin derivative containing 1,2,3-triazole of benzene; Wherein the molar weight ratio of Benzoyl chloride, propargyl alcohol and triethylamine is 1:1:1;
Or,
Chlorinated benzene formyl chloride and propargyl alcohol, in trichloromethane, are added to triethylamine, under condition of ice bath, react 1-2h, then back flow reaction 2-3h, obtains Chlorobenzoic Acid alkynes propyl ester derivative; Chlorobenzoic Acid alkynes propyl ester derivative again with nitrine for acetylize synanthrin, under the catalysis of xitix and copper sulfate, under 60-80 ℃ of condition, react 12-24h, obtain Chlorobenzoic Acid alkynes propyl ester-1,2,3-triazole acetylize synanthrin derivative; Wherein the molar weight ratio of chlorinated benzene formyl chloride, propargyl alcohol and triethylamine is 1:1:1; Chlorinated benzene formyl chloride is:
Described nitrine is dispersed in water for acetylize synanthrin, then adds xitix and copper sulfate to make catalyzer, under homogeneous phase condition not with phenylformic acid alkynes propyl ester or Chlorobenzoic Acid alkynes propyl ester derivatives reaction; It is 30%-40% for acetyl synanthrin molecular fraction that described catalyst sulfuric acid copper addition accounts for nitrine, and the molar weight of xitix is 1-2 times of copper sulfate.
Described nitrine is that synanthrin and N-bromo-succinimide (NBS) are dissolved completely in dry DMF under ice bath for acetylize synanthrin, drips triphenylphosphine (PPh
3) DMF solution, then under 80 ℃ of conditions, react 3h, obtain bromo synanthrin; Bromo synanthrin reacts and spends the night in anhydrous pyridine with diacetyl oxide again under room temperature, obtains bromo acetylize synanthrin; Bromo acetylize synanthrin reacts 4h with sodium azide again in dry DMF under 80 ℃ of conditions, obtains nitrine for acetylize synanthrin;
Wherein, described synanthrin, NBS and PPh
3molar weight ratio is about 1:4:4 in order; Diacetyl oxide addition is 1-2 times of bromo synanthrin molar weight; Sodiumazide addition is 2 times of bromo acetylize synanthrin molar weight.
Described one contains the synanthrin derivative of 1,2,3-triazole for the preparation of sterilant.
The present invention has advantages of:
(1) the present invention obtains the novel synanthrin derivative containing 1,2,3-triazole by effective synthesizing mean, and synthesis condition is easily controlled, and productive rate is high, and cost is lower.
(2) the present invention introduces after ethanoyl, has reduced the water-absorbent of synanthrin in building-up process, and intermediate product can directly be washed, simple to operate, and productive rate improves.
(3) the present invention has introduced triazole ring and the phenyl ring with good bacteriostatic activity, can further improve synanthrin at agricultural chemicals, medicine, the use in the fields such as food.
(4) the present invention is based on active superposition theorem and obtain synthetic route, synanthrin nontoxic, natural reproducible is carried out to structural modification, by substructure, splice the triazole group of high bacteriostatic activity is introduced to synanthrin molecule, obtain having amphipathic one containing 1, the synanthrin derivative of 2,3-triazole.Wish that amphipathic synanthrin and triazole group act synergistically, keep the characteristic of synanthrin Nantural non-toxic, easy degraded simultaneously.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram of synanthrin.
Fig. 2 is the infrared spectrogram of the intermediate product nitrine that obtains of the present invention for acetylize synanthrin, as can be seen from Figure 2 compared with synanthrin raw material, and 1735cm
-1the charateristic avsorption band that the absorption peak at place is ethanoyl, 2105cm
-1absorption peak (the J.Ren that the absorption peak at place is azido-, P.Wang, F.Dong, Y.Feng, D.Peng, Z.Guo, Carbohydrate Polymers, 87 (2012) 1744-1748. Sun Yuan beautiful jades, Cui Wuwei, Gu little Hong, Tang Jian, Shen Ruiling. fourier transform infrared spectroscopy is measured the gamma value [J] of Radix Angelicae Sinensis pectin polysaccharide. spectroscopy and spectroscopic analysis, 2009, 29(3): 682-685. wins Geril Tu, Hu Cha, Liu Guoguang, the selectivity one-step synthesis [J] of Zhong Guiyun .6-nitrine-6-Deoxy curdlan. SCI, 2001 (4): 706-708.), above digital proof nitrine is synthetic for acetylize synanthrin.
Fig. 3-6 are the infrared spectrogram containing the synanthrin derivative of 1,2,3-triazole that the present invention obtains, from Fig. 3-6 known with Fig. 2 nitrine for compared with acetylize synanthrin, the 2105cm in Fig. 2
-1disappear, 1450-1600cm
-1, 650-900cm
-1there is the charateristic avsorption band (Wen Lirong of phenyl ring in place; Li Ming; Zhao Guilong. Substituents on Benzene Skeleton Vibration in IR Spectra affect rule [J]. spectrographic laboratory; 2004,21(2): 244-247.), simultaneously; the absorption peak of ethanoyl does not disappear; a kind of synanthrin derivative containing 1,2,3-triazole of above digital proof is synthetic.
Embodiment
With way of example, the invention will be further described more below, provides implementation detail of the present invention, but be not intended to limit protection scope of the present invention.
A kind of synanthrin containing 1,2,3-triazole is the compound shown in formula (1).
A kind of synanthrin derivative containing 1,2,3-triazole is the compound shown in formula (1).
A kind of containing 1,2, the preparation of the synanthrin of 3-triazole: 0.1mol propargyl alcohol is joined in 30mL trichloromethane, add 0.1mol triethylamine, under ice-water bath, drip the chloroform soln 10mL that contains the chlorinated benzene formyl chloride shown in 0.1mol Benzoyl chloride or compd A, B or C, room temperature reaction 1-2h, TLC monitoring reaction (ethyl acetate: sherwood oil=1:3).After finishing, reaction adds saturated sodium bicarbonate 50mL extraction, extraction liquid is successively with saturated nacl aqueous solution, water washing, dry, filtration, precipitation obtains resistates, resistates column chromatography (ethyl acetate: sherwood oil=1:10 makees eluent) 16-18.0g oily liquids, obtain compound 1 phenylformic acid or Chlorobenzoic Acid alkynes propyl ester structural formula is as follows.
Get 10mmol nitrine for acetylize synanthrin, 10mmol phenylformic acid or Chlorobenzoic Acid alkynes propyl ester, 0.7g xitix, 0.5g copper sulfate, joins in 50mL water, reacts 12h at 60 ℃.Resistates alcohol precipitation, suction filtration, repeatedly washs with ethanol, water successively, and vacuum lyophilization obtains the synanthrin derivative containing 1,2,3-triazole.
Wherein synanthrin (Inulin) by D-fructofuranose molecule with β-(2,1) glycosidic link connects generation, and each synanthrin molecule end connects a glucosyl residue with α-(1,2) glycosidic link, the polymerization degree is generally 10～35, and mean polymerisation degree is 10.
Embodiment 2
A kind of containing 1,2, the preparation of the synanthrin of 3-triazole: 0.2mol propargyl alcohol is joined in 30mL trichloromethane, add 0.1mol triethylamine, under ice-water bath, drip the chloroform soln 10mL that contains the chlorinated benzene formyl chloride shown in 0.1mol Benzoyl chloride or compd A, B or C, 45 ℃ of reaction 1-2h, TLC monitoring reaction (ethyl acetate: sherwood oil=1:3).After finishing, reaction adds saturated sodium bicarbonate 50mL extraction, extraction liquid is successively with saturated nacl aqueous solution, water washing, dry, filtration, precipitation obtains resistates, resistates column chromatography (ethyl acetate: sherwood oil=1:10 makees eluent) must about 15-16.0g oily liquids, obtains compound 1 phenylformic acid or Chlorobenzoic Acid alkynes propyl ester.
Get 10mmol nitrine for acetylize synanthrin, 10mmol compound 1,0.7g xitix, 0.5g copper sulfate, joins in 50mL water, reacts 8h at 60 ℃.Resistates alcohol precipitation, suction filtration, repeatedly washs with ethanol, water successively, and vacuum lyophilization obtains a kind of synanthrin derivative that contains 1,2,3-triazole.
Embodiment 3
A kind of containing 1; 2; the preparation of the synanthrin of 3-triazole: 0.2mol propargyl alcohol is joined in 30mL trichloromethane; add 0.1mol triethylamine; under ice-water bath, drip the chloroform soln 10mL that contains the chlorinated benzene formyl chloride shown in 0.1mol benzoyl or compd A, B or C; room temperature ℃ reaction 3-4h, TLC monitoring reaction (ethyl acetate: sherwood oil=1:3).After finishing, reaction adds saturated sodium bicarbonate 50mL extraction, extraction liquid is successively with saturated nacl aqueous solution, water washing, dry, filtration, precipitation obtains resistates, resistates column chromatography (ethyl acetate: sherwood oil=1:10 makees eluent) must about 14-17.0g oily liquids, obtains compound 1 phenylformic acid or Chlorobenzoic Acid alkynes propyl ester.
Get 10mmol nitrine for acetylize synanthrin, 15mmol compound 1,0.7g xitix, 0.5g copper sulfate, joins in 50mL water, reacts 8h at 60 ℃.Resistates alcohol precipitation, suction filtration, repeatedly washs with ethanol, water successively, and vacuum lyophilization obtains the synanthrin of target product containing 1,2,3-triazole.
Application examples
Antibacterial Activity
1. for examination bacterial classification
Intestinal bacteria (Es-cherichiacoli), preserve bacterial classification and use after 2 tube rejuvenation in refrigerator.
2. culture medium prescription
Table 1LB culture medium prescription (g/L, pH=7.0) (1L)
| Reagent name | Weight |
| Tryptones | 10g |
| Yeast extract | 5g |
| Sodium-chlor | 10g |
| Pure water | 1000g |
3. substratum preparation and preparation of samples
According to upper culture medium prescription ratio, in turn take peptone, yeast extract, peptone, NaCl and put into beaker.In above-mentioned beaker, can first add and be less than the needed water yield, stir evenly with glass rod, then heating makes its dissolving.After medicine dissolves completely, 1000mL keeps the skin wet.Not adjusting before pH, first with pH meter, measure the original pH value of substratum, if pH meta-acid dropwise adds 1mol/L NaOH with dropper in substratum, the stirring of limit edged, and with pH meter, survey its pH value at any time, until pH reaches 7.0.Otherwise, with 1mol/L HCl, regulate.The substratum of preparation is distributed in Erlenmeyer flask, and packing volume is respectively tri-kinds of 16mL, 18mL and 20mL.By preparation, substratum after packing with 1.05kg/cm
2, 121.3 ℃, 20 minutes high pressure steam sterilizations.Take out after cooling standby.
Target product to be measured scatter with sterilized water, and preparation original concentration is 5mg/mL.
4. the mensuration of bacteriostatic activity
Adopt Nephelometric Determination above-described embodiment prepare gained containing the synanthrin derivative (with lower label 1-4) of 1,2,3-triazole to the colibacillary inhibition of Gram-negative bacteria.Test respectively 3 sample concentrations and be 0.1mg/mL, 0.5mg/mL and 1mg/mL cultivate 4 hours, 8 hours, 16 hours and 24 hours inhibiting rate to these pathogenic bacterium.
In Bechtop, respectively 4mL, 2mL and 0.4mL sample solution are joined in 16mL, 18mL and tri-kinds of substratum of 20mL, be mixed with samples contg and be respectively the substratum of 1mg/mL, 0.5mg/mL and 0.1mg/mL.Test is respectively with the positive contrast of isocyatic Azythromycin, with the negative contrast of isopyknic sterile purified water, take isopyknic substratum as blank, in the substratum containing sample and contrast preparing above, access after the bacteria suspension for examination bacterium after isopyknic rejuvenation respectively, at 37 ℃, cultivate 24 hours.In culturing process, measuring respectively bacteria suspension in Erlenmeyer flask is the absorbancy at 600nm place at wavelength in 4 hours, 8 hours, 16 hours and 24 hours, the bacteriostasis rate of calculation sample, and total Test repeats once, according to following formula, calculates bacteriostasis rate:
5. experimental result
A kind of containing 1 as can be seen from Table 2,2, the synanthrin derivative of 3-triazole is with respect to the synanthrin that there is no bacteriostatic activity, intestinal bacteria are had to the activity of certain inhibition when the higher concentration, and bacteriostatic activity strengthens with the increase of sample concentration, along with the prolongation bacteriostatic activity of incubation time slightly declines.
Table 2 Chlorobenzoic Acid class alkynes propyl ester-1,2,3-triazole acetylize synanthrin
Claims (5)
1. alkynes propyl ester-1 of a replacement, 2,3-triazole acetylize synanthrin derivative, is characterized in that: derivant structure formula as the formula (1),
In formula (1), R is H or Cl, and wherein Cl is positioned at 2,3 or 4;
The average span of polymerization degree n is 10-35.
2. by alkynes propyl ester-1 of replacement claimed in claim 1, the preparation method of 2,3-triazole acetylize synanthrin derivative, is characterized in that:
Benzoyl chloride and propargyl alcohol, in trichloromethane, are added to triethylamine, under condition of ice bath, react 1-2h, then back flow reaction 2-3h, obtains phenylformic acid alkynes propyl ester derivative; Phenylformic acid alkynes propyl ester derivative again with nitrine for acetylize synanthrin, under the catalysis of xitix and copper sulfate, under 60-80 ℃ of condition, react 12-24h, obtain phenylformic acid alkynes propyl ester-1,2,3-triazole acetylize synanthrin derivative; Wherein the molar weight ratio of Benzoyl chloride, propargyl alcohol and triethylamine is 1:1:1;
Or,
Chlorinated benzene formyl chloride and propargyl alcohol, in trichloromethane, are added to triethylamine, under condition of ice bath, react 1-2h, then back flow reaction 2-3h, obtains Chlorobenzoic Acid alkynes propyl ester derivative; Chlorobenzoic Acid alkynes propyl ester derivative again with nitrine for acetylize synanthrin, under the catalysis of xitix and copper sulfate, under 60-80 ℃ of condition, react 12-24h, obtain Chlorobenzoic Acid alkynes propyl ester-1,2,3-triazole acetylize synanthrin derivative; Wherein the molar weight ratio of chlorinated benzene formyl chloride, propargyl alcohol and triethylamine is 1:1:1; Chlorinated benzene formyl chloride is:
3. by alkynes propyl ester-1 of replacement claimed in claim 2, the preparation method of 2,3-triazole acetylize synanthrin derivative, is characterized in that:
Described nitrine is dispersed in water for acetylize synanthrin, then adds xitix and copper sulfate to make catalyzer, under homogeneous phase condition not with phenylformic acid alkynes propyl ester-1,2,3-triazole acetylize synanthrin derivative or Chlorobenzoic Acid alkynes propyl ester-1,2,3-triazole acetylize synanthrin derivatives reaction; It is 30%-40% for acetyl synanthrin molecular fraction that described catalyst sulfuric acid copper addition accounts for nitrine, and the molar weight of xitix is 1-2 times of copper sulfate.
4. by alkynes propyl ester-1 of the replacement described in claim 2 or 3, the preparation method of 2,3-triazole acetylize synanthrin derivative, is characterized in that:
Described nitrine is that synanthrin and N-bromo-succinimide (NBS) are dissolved completely in dry DMF under ice bath for acetylize synanthrin, drips triphenylphosphine (PPh
3) DMF solution, then under 80 ℃ of conditions, react 3h, obtain bromo synanthrin; Bromo synanthrin reacts and spends the night in anhydrous pyridine with diacetyl oxide again under room temperature, obtains bromo acetylize synanthrin; Bromo acetylize synanthrin reacts 4h with sodium azide again in dry DMF under 80 ℃ of conditions, obtains nitrine for acetylize synanthrin;
Wherein, described synanthrin, NBS and PPh
3molar weight ratio is about 1:4:4 in order; Diacetyl oxide addition is 1-2 times of bromo synanthrin molar weight; Sodiumazide addition is 2 times of bromo acetylize synanthrin molar weight.
5. by alkynes propyl ester-1 of replacement claimed in claim 1, the application of 2,3-triazole acetylize synanthrin derivative, is characterized in that: alkynes propyl ester-1 of described replacement, 2,3-triazole acetylize synanthrin derivative is for the preparation of sterilant.
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| CN108676040A (en) * | 2018-06-28 | 2018-10-19 | 中国科学院烟台海岸带研究所 | A kind of preparation method and application of 1,2,3- triazoles diphenyl phosphate synanthrin derivative |
| CN108676105A (en) * | 2018-06-12 | 2018-10-19 | 中国科学院烟台海岸带研究所 | A kind of synanthrin triazolium salt and its preparation method and application |
| CN110003364A (en) * | 2019-04-10 | 2019-07-12 | 中国科学院烟台海岸带研究所 | A kind of synanthrin derivative and its preparation method and application containing schiff bases |
| CN116023525A (en) * | 2023-02-13 | 2023-04-28 | 湖北工程学院 | 2-position (1, 4-disubstituted-1, 2, 3-triazole) modified chitosan derivative and preparation method and application thereof |
| CN116589610A (en) * | 2023-07-17 | 2023-08-15 | 中国科学院烟台海岸带研究所 | Amphiphilic chitosan lipoic acid grafted derivative and preparation and application thereof |
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| CN108676105A (en) * | 2018-06-12 | 2018-10-19 | 中国科学院烟台海岸带研究所 | A kind of synanthrin triazolium salt and its preparation method and application |
| CN108676040A (en) * | 2018-06-28 | 2018-10-19 | 中国科学院烟台海岸带研究所 | A kind of preparation method and application of 1,2,3- triazoles diphenyl phosphate synanthrin derivative |
| CN110003364A (en) * | 2019-04-10 | 2019-07-12 | 中国科学院烟台海岸带研究所 | A kind of synanthrin derivative and its preparation method and application containing schiff bases |
| CN116023525A (en) * | 2023-02-13 | 2023-04-28 | 湖北工程学院 | 2-position (1, 4-disubstituted-1, 2, 3-triazole) modified chitosan derivative and preparation method and application thereof |
| CN116023525B (en) * | 2023-02-13 | 2024-03-15 | 湖北工程学院 | 2-position (1, 4-disubstituted-1, 2, 3-triazole) modified chitosan derivative and preparation method and application thereof |
| CN116589610A (en) * | 2023-07-17 | 2023-08-15 | 中国科学院烟台海岸带研究所 | Amphiphilic chitosan lipoic acid grafted derivative and preparation and application thereof |
| CN116589610B (en) * | 2023-07-17 | 2023-10-03 | 中国科学院烟台海岸带研究所 | Amphiphilic chitosan lipoic acid grafted derivative and preparation and application thereof |
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