CN111808062A - Osthole sulfonate compound and application thereof - Google Patents

Osthole sulfonate compound and application thereof Download PDF

Info

Publication number
CN111808062A
CN111808062A CN202010739941.2A CN202010739941A CN111808062A CN 111808062 A CN111808062 A CN 111808062A CN 202010739941 A CN202010739941 A CN 202010739941A CN 111808062 A CN111808062 A CN 111808062A
Authority
CN
China
Prior art keywords
osthole
carried out
reaction
added
compound
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.)
Granted
Application number
CN202010739941.2A
Other languages
Chinese (zh)
Other versions
CN111808062B (en
Inventor
杨家强
安家丽
周绪容
郑洁
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zunyi Medical University
Original Assignee
Zunyi Medical University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Zunyi Medical University filed Critical Zunyi Medical University
Priority to CN202010739941.2A priority Critical patent/CN111808062B/en
Publication of CN111808062A publication Critical patent/CN111808062A/en
Application granted granted Critical
Publication of CN111808062B publication Critical patent/CN111808062B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • 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
    • A01N43/14—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 six-membered rings
    • A01N43/16—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 six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Oncology (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The scheme discloses osthole sulfonate compounds shown as a general formula III in the technical field of organic chemistry,

Description

Osthole sulfonate compound and application thereof
Technical Field
The invention relates to the field of organic chemistry, in particular to an osthole sulfonate compound and application thereof.
Background
Osthole is also called methoxy parsley phenol or parsley phenol methyl ether, and has chemical formulaIs C15H16O3The coumarin is shown in formula 1, has a chemical name of 7-methoxy-8-isopentenyl coumarin, is an effective chemical component of alkyl coumarin with the highest content in fructus Cnidii, is mainly present in plants of Umbelliferae and Rutaceae, and is distributed in feverfew and leguminous plants.
Figure 2
Modern pharmacological experiment research shows that: fructus Cnidii and osthole have wide bioactivity, and have effects of resisting arrhythmia, hypertension, aging, convulsion, inflammation, allergy, tumor, hepatitis, blood sugar, tranquilizing, and memory; meanwhile, agricultural application research is also reported, for example, research shows that osthole has the effects of killing insects, inhibiting viruses and the like.
Therefore, scholars at home and abroad begin to modify and transform the structure of the natural product osthole, and aim to obtain osthole derivatives with good biological activity and research value. Through analysis of existing research documents, application research reports of osthole in the aspect of antibiosis are few, and only research reports that fructus cnidii and extracts have antibacterial activity (1, plum, red poplar, fructus cnidii effective components have influence on the activity of staphylococcus aureus coagulase [ J ]. Guangdong medicine, 2007,28(6): 876-. Therefore, in order to search for antibacterial candidate compounds with novel structures, the invention takes the monomeric compound osthole extracted and separated from the traditional Chinese medicine fructus cnidii as a lead compound, applies theoretical knowledge such as pharmaceutical chemistry, organic synthesis and the like to carry out structural modification and modification on the 8-site isopentenyl group of the osthole, designs and synthesizes an osthole sulfonate compound, and carries out antibacterial activity research.
Disclosure of Invention
The invention takes the osthole extracted and separated from the traditional Chinese medicine common cnidium fruit as a lead compound, applies knowledge such as modern medicine design concept, organic synthesis technology and the like to carry out structural modification and modification on the 8-site isopentenyl group of the osthole, designs and synthesizes osthole sulfonate compounds, and carries out antibacterial activity research.
The invention mainly aims to provide an osthole sulfonate compound, which is shown as a general formula III:
Figure BDA0002606363870000021
wherein R is a substituent group with 1-6 carbon atoms; or R is phenyl; or R is a five-membered aromatic heterocyclic group containing 1 or 2 or 3 heteroatoms of N, O, S atoms; or R is a six-membered aromatic heterocyclic group containing 1 or 2 or 3 heteroatoms selected from N, O, S atoms.
The active osthole sulfonate compound shown in the general formula III can be combined with clinical antibacterial drugs or antibacterial active ingredients for use.
The osthole sulfonate compound shown in the general formula III can be used for preparing medicines or pharmaceutical compositions for resisting staphylococcus aureus (S.aureus).
The osthole sulfonate compound shown in the general formula III can be used for preparing medicines or medicinal compositions for resisting methicillin-resistant staphylococcus aureus.
The following synthetic schemes describe the preparation of the compounds of formula III of the present invention, which are conventional and well known in the art of organic synthesis.
Figure BDA0002606363870000022
Wherein SeO2Is selenium dioxide, NaBH4Is sodium borohydride, Et3N is triethylamine.
Compound III-1: r is phenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000031
compound III-2: r is o-methylphenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000032
compound III-3: r is o-methoxyphenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000033
compound III-4: r is o-fluorophenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000034
compound iii-5: r is o-nitrophenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000035
compound III-6: r is o-trifluoromethylphenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000036
compound III-7: r is m-methylphenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000041
compound III-8: r is m-methoxyphenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000042
compound III-9: r is m-fluorophenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000043
compound iii-10: r is m-nitrophenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000044
compound III-11: r is m-trifluoromethylphenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000045
compound III-12: r is p-methylphenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000046
compound III-13: r is p-methoxyphenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000047
compound III-14: r is p-fluorophenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000051
compound III-15: r is p-nitrophenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000052
compound III-16: r is p-trifluoromethylphenyl, and the chemical structural formula is as follows:
Figure BDA0002606363870000053
antibacterial activity research is carried out on the osthole sulfonate compound provided by the invention, and the result shows that: part of target compounds have obvious antibacterial activity, and especially the antibacterial activity on staphylococcus aureus and methicillin-resistant staphylococcus aureus is far better than that of osthole and sulfadiazine serving as a contrast agent. The invention shows that the structural modification and modification of 8-site of osthole can effectively improve the antibacterial activity of osthole.
Detailed Description
The present invention is further described with reference to the following examples, but the present invention is not limited to the following examples, and it is anticipated that one skilled in the art may make various modifications in combination with the prior art.
Preparation of the compounds of the general formula III of the invention:
Figure BDA0002606363870000054
Figure BDA0002606363870000061
wherein SeO2Is selenium dioxide, NaBH4Is sodium borohydride, Et3N is triethylamine.
Example 1: preparation of Compound III-1
Firstly, 3.0mmol (0.330g) of selenium dioxide is taken to be put into a 100ml three-necked bottle, 25ml of dimethyl sulfoxide is added to be heated and dissolved, 1.0mmol (0.244g) of osthole dissolved in 25ml of dimethyl sulfoxide is added at 100 ℃, TLC tracking reaction is carried out, reflux reaction is carried out for 12min, the reaction is stopped, suction filtration is carried out while the reaction is still hot, filtrate is extracted by 50ml of ethyl acetate, saturated saline and distilled water are used for washing until Ph is 5.5-6, washing liquid is collected, anhydrous sodium sulfate is used for drying, suction filtration and concentration are carried out to obtain a crude product, and the crude product is separated and purified by column chromatography (V)Ethyl acetate:VPetroleum ether1:4) to give a white solid.
Then, 1.0mmol (0.258g) of intermediate I is put into a 100ml three-necked flask, 25ml of absolute ethyl alcohol is added and stirred to be dissolved, 2.0mmol (0.076g) of sodium borohydride is added, TLC tracking reaction is carried out, reaction is carried out for 5h under the condition of room temperature, ethyl acetate 40ml is added for extraction, saturated saline and distilled water are used for washing until the pH value is 5.5-6, washing liquid is collected, anhydrous sodium sulfate is dried, suction filtration and concentration are carried out, a crude product is obtained, and column chromatography separation and purification are carried out (V)Ethyl acetate:VPetroleum ether1:3) to yield a white solid, intermediate ii.
Finally, 1.0mmol (0.260g) of intermediate II is placed in a 50ml reaction tube, 5ml of anhydrous dichloromethane is added and stirred to be dissolved, then 2.0mmol (0.352g) of benzenesulfonyl chloride is added at room temperature, 2.0mmol (0.202g) of triethylamine is slowly added under stirring, after uniform mixing, TLC tracking reaction is carried out, reaction is carried out at 35 ℃ for 24h, concentration is carried out to obtain a crude product, and column chromatography separation and purification (V)Ethyl acetate:VPetroleum ether1:4) to give a white solid, compound iii-1.
Example 2: preparation of Compound III-5
Firstly, 3.0mmol (0.330g) of selenium dioxide is taken to be put into a 100ml three-necked bottle, 25ml of dimethyl sulfoxide is added to be heated and dissolved, 1.0mmol (0.2440g) of osthole dissolved in 25ml of dimethyl sulfoxide is added at 100 ℃, TLC tracking reaction is carried out, reflux reaction is carried out for 12min, the reaction is stopped, suction filtration is carried out while the reaction is still hot, filtrate is extracted by 50ml of ethyl acetate, saturated saline and distilled water are used for washing until the pH value is 5.5-6, washing liquid is collected, anhydrous sodium sulfate is used for drying, suction filtration and concentration are carried out to obtain a crude product, and the crude product is separated and purified by column chromatography (V)Ethyl acetate:VPetroleum ether1:4) to give a white solid.
Then, 1.0mmol (0.258g) of intermediate I is put into a 100Ml three-necked flask, 25Ml of absolute ethyl alcohol is added and stirred to be dissolved, 2.0mmol (0.076g) of sodium borohydride is added, TLC tracking reaction is carried out, reaction is carried out for 5h at room temperature, ethyl acetate 40Ml is added for extraction, saturated saline and distilled water are used for washing until the pH value is 5.5-6, washing liquid is collected, anhydrous sodium sulfate is dried, suction filtration and concentration are carried out to obtain a crude product, and the crude product is separated and purified by column chromatography (V)Ethyl acetate:VPetroleum ether1:3) to yield a white solid, intermediate ii.
Finally, 1.0mmol (0.260g) of intermediate II is placed in a 50ml reaction tube, 5ml of anhydrous dichloromethane is added and stirred to be dissolved, then 3.0mmol (0.663g) of o-nitrobenzenesulfonyl chloride is added at room temperature, 3.0mmol (0.303g) of triethylamine is slowly added under stirring, after uniform mixing, TLC tracking reaction is carried out, reaction is carried out at 35 ℃ for 24h, concentration is carried out to obtain a crude product, and column chromatography separation and purification (V)Ethyl acetate:VPetroleum ether1:3) to give a white solid, compound iii-5.
Example 3: preparation of Compound III-9
Firstly, 3.0mmol (0.330g) of selenium dioxide is taken to be put into a 100ml three-necked bottle, 25ml of dimethyl sulfoxide is added to be heated and dissolved, 1.0mmol (0.244g) of osthole dissolved in 25ml of dimethyl sulfoxide is added at 100 ℃, TLC tracking reaction is carried out, reflux reaction is carried out for 12min, the reaction is stopped, suction filtration is carried out while the reaction is still hot, filtrate is extracted by 50ml of ethyl acetate, saturated saline and distilled water are used for washing until the pH value is 5.5-6, and washing is collectedWashing, drying with anhydrous sodium sulfate, vacuum filtering, concentrating to obtain crude product, and purifying by column chromatography (V)Ethyl acetate:VPetroleum ether1:4) to give a white solid.
Then, 1.0mmol (0.258g) of intermediate I is put into a 100ml three-necked flask, 25ml of absolute ethyl alcohol is added and stirred to be dissolved, 2.0mmol (0.076g) of sodium borohydride is added, TLC tracking reaction is carried out, reaction is carried out for 5h under the condition of room temperature, ethyl acetate 40ml is added for extraction, saturated saline and distilled water are used for washing until the pH value is 5.5-6, washing liquid is collected, anhydrous sodium sulfate is dried, suction filtration and concentration are carried out, a crude product is obtained, and column chromatography separation and purification are carried out (V)Ethyl acetate:VPetroleum ether1:3) to yield a white solid, intermediate ii.
Finally, 1.0mmol (0.260g) of intermediate II is placed in a 50ml reaction tube, 5ml of anhydrous dichloromethane is added and stirred to be dissolved, then 1.5mmol (0.291g) of m-fluorobenzenesulfonyl chloride is added at room temperature, 1.5mmol (0.152g) of triethylamine is slowly added under stirring, after uniform mixing, TLC tracing reaction is carried out, reaction is carried out at 35 ℃ for 24h, concentration is carried out to obtain a crude product, and column chromatography separation and purification (V)Ethyl acetate:VPetroleum ether1:5) to give a white solid, compound iii-9.
Example 4: preparation of Compound III-16
Firstly, 3.0mmol (0.330g) of selenium dioxide is taken to be put into a 100Ml three-necked bottle, 25Ml of dimethyl sulfoxide is added to be heated and dissolved, 1.0mmol (0.244g) of osthole dissolved in 25Ml of dimethyl sulfoxide is added at 100 ℃, TLC tracking reaction is carried out, reflux reaction is carried out for 12min, the reaction is stopped, suction filtration is carried out while the reaction is still hot, filtrate is extracted by 50Ml of ethyl acetate, saturated saline and distilled water are used for washing until the pH value is 5.5-6, washing liquid is collected, anhydrous sodium sulfate is used for drying, suction filtration and concentration, a crude product is obtained, and column chromatography separation and purification (V) are carried outEthyl acetate:VPetroleum ether1:4) to yield a white solid, intermediate I.
Then, 1.0mmol (0.258g) of intermediate I was put in a 100ml three-necked flask, 25ml of anhydrous ethanol was added and stirred to dissolve it, 2.0mmol (0.076g) of sodium borohydride was added, the reaction was followed by TLC, reaction was carried out at room temperature for 5 hours, and then 40ml of ethyl acetate was added and extracted, followed by saturated brine and distilled waterWashing with water until pH is 5.5-6, collecting washing solution, drying with anhydrous sodium sulfate, vacuum filtering, concentrating to obtain crude product, and purifying by column chromatography (V)Ethyl acetate:VPetroleum ether1:3) to yield a white solid, intermediate ii.
Finally, 1.0mmol (0.260g) of intermediate II is placed in a 50ml reaction tube, 5ml of anhydrous dichloromethane is added and stirred to be dissolved, then 2.0mmol (0.488g) of p-trifluoromethylbenzenesulfonyl chloride is added at room temperature, 2.0mmol (0.202g) of triethylamine is slowly added under stirring, after uniform mixing, TLC tracking reaction is carried out, reaction is carried out at 35 ℃ for 24h, concentration is carried out to obtain a crude product, and column chromatography separation and purification (V)Ethyl acetate:VPetroleum ether1:3) to give a white solid, compound iii-16.
The relevant data for target compound iii are shown in table 1:
TABLE 1
Figure BDA0002606363870000081
Figure BDA0002606363870000091
Figure BDA0002606363870000101
The antibacterial activity test of the invention: the Minimum Inhibitory Concentration (MIC) of the osthole sulfonate compound shown in the general formula III on staphylococcus aureus (S.aureus), escherichia coli (E.coli) and methicillin-resistant staphylococcus aureus (MRSA) is determined by a microdilution method by taking osthole and sulfadiazine as reference drugs, and the data are shown in Table 2.
TABLE 2
Figure BDA0002606363870000102
From the above experimental results, it is clear that the compound of formula iii to be protected according to the present invention has potential antibacterial activity. The antibacterial activity of most compounds on staphylococcus aureus (S.aureus), escherichia coli (E.coli) and methicillin-resistant staphylococcus aureus (MRSA) is superior to that of reference osthole and sulfadiazine, and especially the antibacterial activity on staphylococcus aureus (S.aureus) and methicillin-resistant staphylococcus aureus (MRSA) is more obvious. Wherein, the MIC of the compounds III-4, III-6, III-14, III-15 and III-16 to staphylococcus aureus (S.aureus) is far less than that of a reference osthole and a reference sulfadiazine; the MICs of the compounds III-14 and III-16 to methicillin-resistant staphylococcus aureus (MRSA) are far smaller than those of a reference substance osthole and a reference drug sulfadiazine, and the compounds all show obvious antibacterial activity; in addition, the antibacterial effect of the compounds III-6 and III-16 on Escherichia coli (E.coli) is superior to that of reference substances osthole and sulfadiazine, and the compounds show obvious antibacterial activity. The potential antibacterial activity of the compound can be used for preparing medicines for resisting staphylococcus aureus (S.aureus), escherichia coli (E.coli) and methicillin-resistant staphylococcus aureus (MRSA). Also, it can be used in combination with other antibacterial active substances.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.

Claims (4)

1. An osthole sulfonate compound is characterized in that the osthole sulfonate compound has a chemical structure shown in a general formula III:
Figure FDA0002606363860000011
wherein R is a substituent group with 1-6 carbon atoms; or R is phenyl; or R is a five-membered aromatic heterocyclic group containing 1 or 2 or 3 heteroatoms of N, O, S atoms; or R is a six-membered aromatic heterocyclic group containing 1 or 2 or 3 heteroatoms selected from N, O, S atoms.
2. The use of osthole sulfonates according to claim 1 for the preparation of antibacterial medicaments or in combination with antibacterial active ingredients.
3. The use of osthole sulfonates according to claim 1 for the preparation of anti-staphylococcus aureus drugs or pharmaceutical compositions.
4. The use of the osthole sulfonate compound of claim 1 in the preparation of a methicillin-resistant staphylococcus aureus medicament or pharmaceutical composition.
CN202010739941.2A 2020-07-28 2020-07-28 Osthole sulfonate compound and application thereof Active CN111808062B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202010739941.2A CN111808062B (en) 2020-07-28 2020-07-28 Osthole sulfonate compound and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010739941.2A CN111808062B (en) 2020-07-28 2020-07-28 Osthole sulfonate compound and application thereof

Publications (2)

Publication Number Publication Date
CN111808062A true CN111808062A (en) 2020-10-23
CN111808062B CN111808062B (en) 2022-09-13

Family

ID=72862922

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010739941.2A Active CN111808062B (en) 2020-07-28 2020-07-28 Osthole sulfonate compound and application thereof

Country Status (1)

Country Link
CN (1) CN111808062B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114805111A (en) * 2022-05-23 2022-07-29 遵义医科大学 Phenylacrylamide compound and preparation method and application thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2005267385A1 (en) * 2004-06-25 2006-02-02 Janssen Pharmaceutica N.V. Quaternary salt CCR2 antagonists
CN103554075A (en) * 2013-10-30 2014-02-05 南京农业大学 New method for preparing osthol analogue
CN109678900A (en) * 2019-01-30 2019-04-26 遵义医学院 A kind of sulphone amide derivative and the preparation method and application thereof
CN110003160A (en) * 2019-05-14 2019-07-12 贵州中医药大学 A kind of Osthole hydrazone class/acylhydrazone class/sulphur acylhydrazone and preparation method thereof and application

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2005267385A1 (en) * 2004-06-25 2006-02-02 Janssen Pharmaceutica N.V. Quaternary salt CCR2 antagonists
CN103554075A (en) * 2013-10-30 2014-02-05 南京农业大学 New method for preparing osthol analogue
CN109678900A (en) * 2019-01-30 2019-04-26 遵义医学院 A kind of sulphone amide derivative and the preparation method and application thereof
CN110003160A (en) * 2019-05-14 2019-07-12 贵州中医药大学 A kind of Osthole hydrazone class/acylhydrazone class/sulphur acylhydrazone and preparation method thereof and application

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
杨家强，等: "新型蛇床子素磺酸酯衍生物的合成与抗菌活性研究", 《中国药学杂志》 *
王栋等: "8种4-甲基香豆素衍生物的合成及其农药活性", 《中国农学通报》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114805111A (en) * 2022-05-23 2022-07-29 遵义医科大学 Phenylacrylamide compound and preparation method and application thereof
CN114805111B (en) * 2022-05-23 2024-02-06 遵义医科大学 Benzeneacrylamide compound and preparation method and application thereof

Also Published As

Publication number Publication date
CN111808062B (en) 2022-09-13

Similar Documents

Publication Publication Date Title
CA3029857C (en) Aromatic acetylene or aromatic ethylene compound, intermediate, preparation method, pharmaceutical composition and use thereof
SU1248533A3 (en) Method of producing sulfamoyl-substituted derivatives of phenethylamine or hydrochloride thereof
CN102397269B (en) Application of chalcone compounds in preparations of inflammation resisting medicines
CN110627755B (en) Gamma-butyrolactone dimer anticancer compound and preparation method thereof
CN111747917B (en) Osthole amide compound and application thereof
CN111808062B (en) Osthole sulfonate compound and application thereof
CN111732565B (en) Osthole ester compound and application thereof
PL234609B1 (en) 8-O-β-D-4"-methoxyglucopyranosyl-6-methylflavone and method for producing 8-O-β-D-4"-methoxyglucopyranosyl-6-methylflavone
CN115785070B (en) Pyrrolidinyl acetamide derivative, preparation method and application thereof
CN108276367A (en) A kind of bromo-furanone ester type compound and preparation method thereof and its application
CN103524318A (en) Application of allyl-containing monocarbonyl curcumin analogs in preparing antiinflammatory drugs
CN111592520B (en) 4, 5-disubstituted piperine derivatives, and preparation method and application thereof
CN111171114B (en) Phosphonate dipeptide compound and application thereof
CN102443005A (en) Spiroheterocycle compound of chalcone and application of spiroheterocycle compound
CN109053798B (en) Rhein ester derivative and preparation method and application thereof
CN106674180B (en) A kind of quercetin derivative and its preparation method and application
CN101137609B (en) Desmosdumotin, its production method and application against tumour and AIDS
KR100516647B1 (en) Hypoglycemic composition
CN105439889B (en) A kind of vanillic aldehyde amine noval chemical compound, its preparation method and medical usage
CN111825608A (en) Tetrahydroquinoline and tetrahydroisoquinoline compounds and application thereof
CN115448826B (en) Separation and identification of natural borneol metabolites
CN111303087B (en) Furanone compound and preparation method and application thereof
CN110963894B (en) Andrographolide compound and preparation method and application thereof
EP0347305B1 (en) [(Aryl-4-piperazinyl-1)-2-ethoxy]-3 p cymene, the ortho-, meta-, para-monosubstituted or disubstituted phenyl ring derivatives, process for their preparation and medicaments containing the same as the active principle
CN111217824B (en) 4-O-arylaminopropyl glycyrrhiza A derivative and preparation and application thereof

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