CN109970704B - Chalcone derivative containing thiophene sulfonate, and preparation method and application thereof - Google Patents
Chalcone derivative containing thiophene sulfonate, and preparation method and application thereof Download PDFInfo
- Publication number
- CN109970704B CN109970704B CN201910323716.8A CN201910323716A CN109970704B CN 109970704 B CN109970704 B CN 109970704B CN 201910323716 A CN201910323716 A CN 201910323716A CN 109970704 B CN109970704 B CN 109970704B
- Authority
- CN
- China
- Prior art keywords
- sulfonate
- thiophene
- prop
- synthesis
- chalcone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
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)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a chalcone derivative containing thiophene sulfonate, which is characterized in that: the general formula is as follows:
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to chalcone derivatives containing thiophene sulfonate, a preparation method of the chalcone derivatives containing thiophene sulfonate and application of the chalcone derivatives containing thiophene sulfonate in inhibiting plant bacterial activity.
Background
Chalcone belongs to a flavonoid compound, and is easy to combine with receptors with different structures to form chalcone derivatives with different structures due to the fact that molecules of the chalcone are flexible structures, and the derivatives have wide biological activities of sterilization, disinsection, weeding, antivirus, anti-tumor, anti-inflammation, antioxidation and the like, and are widely applied to the fields of chemical and biological research. Recent related reports show that chalcone compounds have extremely good bacteriostatic activity, so that organic active molecules with excellent bacteriostatic activity can be obtained by modifying the structure of the chalcone compounds serving as a lead.
In 2016, Ganhuai et al (Chinese science and chemistry, 2016,46:1204-50The value is 20.9 mug/mL, which is obviously better than the reference medicament ningnanmycin (37.9 mug/mL).
In 2018, strict Yingkun et al (organic chemistry, 2018,38: 1763-. The broad bean aphid and the cabbage caterpillar are taken as targets, and the insecticidal activity of the synthetic compound is tested in the laboratory. The results show that most compounds have some poisoning activity against both pests. Wherein the compound (E) -N- (3- (3- (5-bromothiophene-2-yl) acryloyl) phenyl) -2-hydroxyacetamide has LC (L-phenylalanine) on cabbage caterpillar50The poisoning effect of the cypermethrin (LC) is 6.6 mu g/mL509.2. mu.g/mL) is more preferable.
Thiophene sulfonate contains a sulfonyl group (S ═ O), has strong polarity and is an important active group; the special structure and properties of the material make the material have the advantages of high chemical activity, many reaction sites and the like. The thiophene sulfoacid ester has the advantages of low price, easy obtaining, easy storage, stable structure and the like, and the thiophene sulfoacid ester and the derivative thereof are used as insecticides, bactericides, herbicides, plant growth regulators, food additives, anticancer drugs and the like and are widely applied to the aspects of industry, agriculture, pharmacy and the like. In addition, the thiol compound can be used as a thiol compound in the synthesis of a sulfur-containing compound.
In 2017, substituted sulfonate is introduced into triazole to design and synthesize a series of triazole-containing sulfonate compounds (Hubei: CN106879599A,2017,06,23.) and the like, the antibacterial activity of a target compound is tested by a turbidity method, and preliminary measurement results show that the inhibition rate of the compound 4- (4-chloro-2-methylphenoxy) phenyl 1- (N, N-dimethylsulfamoyl) -1H-1,2, 4-triazole-3-sulfonate on rice bacterial leaf blight reaches 96.5% respectively at the concentration of 20 mu g/mL.
In 2018, Xihaojiao et al (organic chemistry, 2018,38:1680-, the inhibition rate of 4-dimethoxyphenyl) -5H-benzothieno [3',2':2,3] pyrido [4,5-d ] pyrido [1,2-a ] pyrimidinone on sclerotinia sclerotiorum is 98%.
In conclusion, the compounds containing chalcone and thiophene sulfonate have better biological activity, but no report about introducing thiophene sulfonate into a chalcone structure and testing the inhibition of plant bacterial activity is found.
Disclosure of Invention
The invention aims to provide a chalcone derivative containing thiophene sulfonate and a preparation method thereof.
It is a further object of the present invention to test the performance results of the thiophene sulfonate containing chalcone derivatives in inhibiting plant bacterial activity.
The invention relates to chalcone derivatives containing thiophene sulfonate, which have the following general formula:
wherein: r is substituted phenyl or substituted aromatic heterocyclic radical.
The substituted phenyl is an alkyl group containing one or more than one C1-C6, an alkoxy group containing C1-C6, a nitro group or a halogen atom on the ortho, meta, para or the two positions of the benzene ring; the R-substituted aromatic heterocyclic group is furyl, pyridyl, thienyl or pyrrolyl, or thiazolyl heterocyclic ring which contains C1-C6 alkyl, C1-C6 alkoxy, nitro or halogen atom.
The synthetic route of the chalcone derivative containing thiophene sulfonate is as follows:
the chalcone derivative containing thiophene sulfonate is applied to inhibiting the activity of plant bacteria.
The chalcone derivative containing thiophene sulfonate is applied to the aspect of being used as a medicament for inhibiting rice bacterial blight, citrus canker pathogen and tobacco bacterial wilt.
Compared with the prior art, the invention has obvious beneficial effects, and the technical scheme can show that: the invention uses 1- (4-hydroxyphenyl) -3- (substituted aryl) prop-2-ene-1-ketone and thiophene sulfonate with excellent biological activity to react to generate chalcone derivatives containing the thiophene sulfonate, and the plant bacteria inhibiting activity of the target compound is measured when the concentration is 100 mu g/mL and 50 mu g/mL. The result of the bacteriostatic activity test shows that: under the concentration tested by experiments, most compounds have good inhibitory activity on rice bacterial blight, tobacco bacterial wilt and citrus canker pathogen, and can be used for preparing plant pathogen inhibition medicaments. The preparation method comprises the steps of carrying out aldol condensation reaction on 4-hydroxyacetophenone and substituted aromatic formaldehyde to generate 1- (4-hydroxyphenyl) -3- (substituted aryl) prop-2-ene-1-one, and reacting the 1- (4-hydroxyphenyl) -3- (substituted aryl) prop-2-ene-1-one with thiophene sulfonate to generate the chalcone derivative containing the thiophene sulfonate. The preparation method takes 4-hydroxyacetophenone, substituted aromatic aldehyde and thiophene sulfonyl chloride as raw materials, which are common organic reagents and solvents, and the raw materials are easy to obtain. The method can react at normal temperature or lower temperature, the reaction condition is mild, the post-treatment is simple, and the yield is high and can reach 56-68%.
Detailed Description
Example 1
(E) -synthesis of 3-phenyl-1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B1) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: adding 4- (hydroxyacetophenone (4.0g), benzaldehyde (4.0g) and 100mL of ethanol into a 500mL three-neck flask, stirring for about 30min, adding 24mL of 4mol/L NaOH solution into the system, after dropwise addition, stirring in an ice bath for about 12h, after the reaction is finished, transferring the system into a 500mL beaker, adding a proper amount of ice water, adjusting the pH of the system to be about 5-6 by using a 5% dilute hydrochloric acid solution, separating out a large amount of milky solid, and extracting the solid to obtain the yield of 72%.
(2) Synthesis of (E) -3-phenyl-1- (4- (thiophene-2-sulfonate) prop-2-en-1-one: a100 mL round-bottom flask was charged with (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one (1.0g), thiophenesulfonate (1.2g), 30mL acetonitrile and 0.6g potassium carbonate, heated and stirred for 12h, TCL detected new point generation and no change in starting material, extracted with ethyl acetate, distilled under reduced pressure to give crude product, which was purified by silica gel chromatography [ V petroleum ether: and (E) -3-phenyl-1- (4- (thiophene-2-sulfonate) prop-2-ene-1-one is obtained by using the ethyl acetate (1: 2).
Example 2
(E) -synthesis of 3- (2-fluorophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B2) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (2-fluorophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in step (2) of example 1, except that 2-fluorobenzaldehyde was used as a starting material.
Example 3
(E) -synthesis of 3- (3-fluorophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B3) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (3-fluorophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in step (2) of example 1 except that 3-fluorobenzaldehyde was used as a starting material.
Example 4
(E) -synthesis of 3- (4-fluorophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B4) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (4-fluorophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in step (2) of example 1 except that 4-fluorobenzaldehyde was used as a starting material.
Example 5
(E) -synthesis of 3- (4-chlorophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B5) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (4-chlorophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in (2) of example 1, except that 4-chlorobenzaldehyde was used as a starting material.
Example 6
(E) -synthesis of 3- (4-bromophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B6) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (4-bromophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in example 1, step (2), except that 4-bromobenzaldehyde was used as the starting material.
Example 7
(E) -synthesis of 3- (2-pyridylphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B7) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (2-pyridylphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in (2) of example 1, except that 2-pyridylbenzaldehyde was used as a starting material.
Example 8
(E) -synthesis of 3- (3-nitrophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B8) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (3-nitrophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in (2) of example 1, except that 3-nitrobenzaldehyde was used as a starting material.
Example 9
(E) -synthesis of 3- (2-methoxyphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B9), comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (2-methoxyphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in (2) of example 1, except that 2-methoxybenzaldehyde was used as a starting material.
Example 10
(E) -synthesis of 3- (3-methylphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B10), comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (3-methylphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in step (2) of example 1 except that 3-methylbenzaldehyde was used as a starting material.
Example 11
(E) -synthesis of 3- (4-methylphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B11), comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (4-methylphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in step (2) of example 1 except that 4-methylbenzaldehyde was used as a starting material.
Example 12
(E) -synthesis of 3- (3, 4-dimethoxyphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B12) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (3, 4-dimethoxyphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in example 1, step (2), except that 3, 4-dimethoxybenzaldehyde was used as the starting material.
Example 13
(E) Synthesis of (compound No. B13) 3- (3, 4-dichlorophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (3, 4-dichlorophenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in example 1, step (2), except that 3, 4-dichlorobenzaldehyde was used as the starting material.
Example 14
(E) Synthesis of (E) -3- (4-isopropylphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B14) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (4-isopropylphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in example 1, step (2), except that 4-isopropylbenzaldehyde was used as a starting material.
Example 15
(E) -synthesis of 3- (3, 4-dimethylphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one (compound No. B15) comprising the following steps:
(1) synthesis of (E) -1- (4-hydroxyphenyl) -3- (phenyl) prop-2-en-1-one: as in step (1) of example 1.
(2) Synthesis of (E) -3- (3, 4-dimethylphenyl) -1- (4- (thiophene-2-sulfonate) prop-2-en-1-one As in step (2) of example 1 except that 3, 4-dimethylbenzaldehyde was used as a starting material.
TABLE 1 physicochemical Properties of the target Compounds and their Mass spectrometric data
TABLE 2 NMR and C spectra data for target compounds
Bacteriostatic activity of the target compound
(the inhibitory Activity of the target Compound against Xanthomonas oryzae (Xanthomonas oryzae pv. oryzae), Xanthomonas citri (Xanthomonas axonopodispv. citri) and Nicotiana tabacum (Ralstonia solanacearum)
The in vitro bacteriostatic activity of the target compound is tested by a turbidity method by taking Xanthomonas oryzae (Xanthomonas oryzae pv. oryzae), Xanthomonas citri (Xanthomonas axonopodisppv. citri) and Nicotiana tabacum (Ralstonia solanacerum) as test objects, taking commercial medicaments of copper thiabendazole (Thiodiazole hopper) and bismerthazol (Bismerthiazol) as positive control medicaments, respectively preparing the samples and the control medicaments into toxic NB-containing liquid culture media with the concentrations of 100 mu g/mL and 50 mu g/mL, and determining the OD value which is the OD value of a sterile medium on the basis of the test tubes. Then inoculating the tested strain, shaking and culturing for 48h at 28 ℃ and 180r/min constant temperature shaking table, and measuring OD value of the bacterium liquid with each concentration on a spectrophotometer, wherein the OD value is the OD value of the bacterium-containing culture medium. The inhibition of the tested compounds was calculated as follows and the results are shown in Table 3.
Inhibition rate (OD value of control culture medium liquid after correction-OD value of toxic medium after correction)/OD value of control culture medium liquid after correction
OD value of bacteria-containing culture medium-OD value of sterile culture medium
TABLE 3 test results of Compounds B1-B15 on Curvularia citrifolia, Fusarium oxysporum f.sp.oryzae and Fusarium oxysporum f.sp.nicotianae
aThree replicates;bthe commercial drugs thiabendazole and bismerthiazol were used as control agents, respectively.
The target compounds B1-B15 and the results of the antibacterial activity test are shown in Table 3. As can be seen from the table, part of the compounds show better inhibitory activity on the pathogen of rice bacterial-blight at a concentration of 100. mu.g/mL, wherein B3 (88.1%) and B8 (82.3%) are higher than those of control medicaments, namely thiabendazole (37.2%) and bismerthiazol (53.8%); the compound shows certain bacteriostatic activity on citrus canker bacteria, wherein B1 (67.5%), B2 (77.2%) and B8 (95.2%) are higher than control medicaments of thiabendazole (57.2%) and bismerthiazol (65.3%); the compound shows certain bacteriostatic activity on ralstonia solanacearum, wherein B10 (91.4%) and B12 (92.4%) are higher than control medicaments of thiabendazole (45.2%) and bismerthiazol (53.7%).
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention in any way, and any simple modification, equivalent change and modification of the above embodiment according to the technical spirit of the present invention are within the scope of the technical solution of the present invention without departing from the technical solution of the present invention.
Claims (4)
1. A chalcone derivative containing thiophene sulfonate is characterized in that: the general formula is as follows:
wherein R is substituted phenyl or substituted aromatic heterocyclic radical; the substituted phenyl is an alkyl group containing one or more than one C1-C6, an alkoxy group containing C1-C6, a nitro group or a halogen atom on the ortho, meta, para or the two positions of the benzene ring; the substituted aromatic heterocyclic group is furyl, pyridyl, thienyl or pyrrolyl, or thiazolyl heterocycle which contains C1-C6 alkyl, C1-C6 alkoxy, nitro or halogen atom.
2. The method for synthesizing chalcone derivatives according to claim 1, wherein:
3. the use of a chalcone derivative according to claim 1, comprising thiophene sulfonate, as a medicament for inhibiting bacterial activity in plants.
4. The use of chalcone derivatives according to claim 1, for inhibiting bacterial blight of rice, citrus canker and ralstonia solanacearum.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910323716.8A CN109970704B (en) | 2019-04-22 | 2019-04-22 | Chalcone derivative containing thiophene sulfonate, and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910323716.8A CN109970704B (en) | 2019-04-22 | 2019-04-22 | Chalcone derivative containing thiophene sulfonate, and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109970704A CN109970704A (en) | 2019-07-05 |
| CN109970704B true CN109970704B (en) | 2022-01-28 |
Family
ID=67085690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910323716.8A Active CN109970704B (en) | 2019-04-22 | 2019-04-22 | Chalcone derivative containing thiophene sulfonate, and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109970704B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114634465B (en) * | 2022-03-09 | 2023-05-30 | 贵州大学 | Pentadienone derivative containing sulfonyl piperazine as well as preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010045395A2 (en) * | 2008-10-14 | 2010-04-22 | Danyang Chen | Curcumin analog compositions and related methods |
| CN102229546A (en) * | 2011-05-12 | 2011-11-02 | 贵州大学 | 1,4-pentadiene-3-ketone compound including sulfonic acid ester group, preparation method and use thereof |
| CN107253915A (en) * | 2010-08-20 | 2017-10-17 | 有联生技股份有限公司 | The assimilation compound of 1,5 diphenyl, penta Isosorbide-5-Nitrae diene 3 |
| CN107602493A (en) * | 2017-08-31 | 2018-01-19 | 贵州大学 | The ketones derivant of 1,4 pentadiene 3, the Preparation method and use of a kind of phentriazine ketone |
| CN108864188A (en) * | 2018-09-06 | 2018-11-23 | 贵州大学 | A kind of 1,4- pentadiene -3- ketones derivant, preparation method and application containing phosphite ester |
-
2019
- 2019-04-22 CN CN201910323716.8A patent/CN109970704B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010045395A2 (en) * | 2008-10-14 | 2010-04-22 | Danyang Chen | Curcumin analog compositions and related methods |
| CN107253915A (en) * | 2010-08-20 | 2017-10-17 | 有联生技股份有限公司 | The assimilation compound of 1,5 diphenyl, penta Isosorbide-5-Nitrae diene 3 |
| CN102229546A (en) * | 2011-05-12 | 2011-11-02 | 贵州大学 | 1,4-pentadiene-3-ketone compound including sulfonic acid ester group, preparation method and use thereof |
| CN107602493A (en) * | 2017-08-31 | 2018-01-19 | 贵州大学 | The ketones derivant of 1,4 pentadiene 3, the Preparation method and use of a kind of phentriazine ketone |
| CN108864188A (en) * | 2018-09-06 | 2018-11-23 | 贵州大学 | A kind of 1,4- pentadiene -3- ketones derivant, preparation method and application containing phosphite ester |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109970704A (en) | 2019-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109942540B (en) | 1, 4-pentadiene-3-ketone derivative containing thiophene sulfonate, preparation method and application thereof | |
| CN108997253B (en) | Mandelic acid derivatives containing 1,3, 4-oxadiazole thioether and application thereof | |
| CN112608307B (en) | Heterocyclic substituted 1,3,4-oxadiazole hydrazide compound as well as preparation method and application thereof | |
| SU1050564A3 (en) | Process for preparing derivatives of nitrothiphene | |
| CN109970704B (en) | Chalcone derivative containing thiophene sulfonate, and preparation method and application thereof | |
| CN108864188B (en) | Phosphite ester-containing 1, 4-pentadiene-3-ketone derivative, and preparation method and application thereof | |
| CN109824610B (en) | Chalcone derivative containing quinoxaline, preparation method and application thereof | |
| CN109251186B (en) | Chalcone derivative containing benzothiazole, and preparation method and application thereof | |
| CN106188011B (en) | The ultrasound synthesis and application of quaternary ring-type beta-lactam derivatives based on arylpyrazole skeleton | |
| CN113004219A (en) | Thiazole ring-containing amide compound and preparation method and application thereof | |
| CN109020916B (en) | Substituted benzothiazole C2 alkylated derivative and application thereof | |
| CN109721559B (en) | 1, 4-pentadiene-3-ketone derivative containing thioether triazole, preparation method and application | |
| CN107056687B (en) | Pyridine group-containing 1, 4-pentadiene-3-ketoxime ester compound, preparation method and application | |
| CN111699182A (en) | Novel methionine metabolic pathway inhibitors | |
| FR2561239A1 (en) | Arylthio-pyridinyl-ALKANOLS | |
| CN109851570B (en) | Chalcone derivative containing 1,2, 4-triazine, preparation method and application thereof | |
| CN109293616B (en) | Coumarin-containing chalcone derivatives, and preparation method and application thereof | |
| CN114181150A (en) | Pyrazole amide derivative, preparation method and application thereof | |
| CN103141486B (en) | Application of 4-(benzofuran-5-yl)-2-phenzyl aminothiazole as bactericide | |
| CN108484521B (en) | Nitrogen heterocyclic macrolide compound containing carbamate or urea structure for pesticide and preparation method and application thereof | |
| CN111393359A (en) | Pyridine salt-containing N- (cinnamoyl) -N' - (substituted) propyl hydrazide compound and preparation method and application thereof | |
| CN114957123B (en) | 3- (difluoromethyl) -pyrazole-4-carboxylic ester derivative and preparation method and application thereof | |
| CN106431977B (en) | A kind of unsaturated oximido ethers compound and application thereof | |
| CN105924435B (en) | A kind of substituted pyrazoles acetamides and its preparation method and application | |
| CN111630032A (en) | Novel methionine metabolic pathway inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |