CN103554077B - Chromone compound as well as preparation method and application thereof - Google Patents
Chromone compound as well as preparation method and application thereof Download PDFInfo
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- CN103554077B CN103554077B CN201310519114.2A CN201310519114A CN103554077B CN 103554077 B CN103554077 B CN 103554077B CN 201310519114 A CN201310519114 A CN 201310519114A CN 103554077 B CN103554077 B CN 103554077B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- 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
- A01N43/22—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 rings with more than six members
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Abstract
The invention discloses a chromone compound as well as a preparation method and application thereof. The chromone compound is obtained by separating from tobacco rootstock, the molecular formula of the chromone compound is C14H13O4 and comprises the structure as shown in the specification. The preparation method of the chromone compound comprises the following steps: on the basis of using the tobacco rootstock as a raw material, extracting extractum, and performing silica column chromatography and high pressure liquid chromatographic separation. The method comprises the following specific steps: crushing the tobacco rootstock sample, extracting ethanol ultrasonic extraction, combining extracting solution, filtering, reducing pressure, and concentrating to obtain the extractum; performing initial chromatography analysis on the extractum by using silica gel dry column-packing; performing gradient elution by using a chloroform-acetone solution in volume ratio of (1:0)-(1:2); further purifying the 8:2 part of eluate by using high pressure liquid chromatographic separation to obtain the chromone compound. The test proves that the chromone compound have good cell activity to tobacco mosaic virus. The compound disclosed by the invention is simple in structure, easy for realization of artificial synthesis and good in activity, and can be used as guiding compound for preventing the tobacco mosaic virus.
Description
Technical field
The invention belongs to tobacco chemistry field, be specifically related to a kind of chromone compounds extracted from tobacco rhizome and preparation method thereof and application.
Background technology
Tobacco is one the abundantest containing chemical substance in each kind of plant of being familiar with of the mankind, and through the research of decades, the monomer chemistries material that people identify out at present from tobacco just more than kind more than 3000, and also has many compositions not yet to identify out.Tobacco, except being mainly used in cigarette smoking purposes, also therefrom can extract the multiple chemical composition having utility value, therefrom finds that there is the guiding compound of value of exploiting and utilizing.Particularly for the root of tobacco and stem, general all as the offal treatment in leaf tobacco production process.Therefore, except as except cigarette consumption, the comprehensive utilization strengthening tobacco and waste thereof is significant.
Chromone compounds is ubiquitous compound in a class natural phant, also be the important component in tobacco, this compounds has pharmacological action widely, as antitumor, anti-human immunodeficiency virus (HIV), anti-oxidant, antibacterial, anticoagulation etc.; Existing research simultaneously confirms, its pharmacological action and chemical structure closely related, more chromone compounds can be researched and developed further, therefrom find effective lead compound and active group.The present invention is separated and obtains a kind of new chromone compounds with activity of resisting tobacco mosaic virus from tobacco rhizome, and this compound it is not yet seen relevant report.
Summary of the invention
The first object of the present invention is to provide a kind of chromone compounds; Second object is the preparation method providing this chromone compounds; 3rd object is that described chromone compounds is preparing the application in resisting tobacco mosaic disease medicine.
The first object of the present invention is achieved in that described compound is separated to obtain from tobacco rhizome, and its molecular formula is C
14h
13o
4, there is following structure:
。
This compound is yellow jelly, and chemical name is: tobacco chromone C (tobchromone C).
It take tobacco rhizome as raw material that the second object of the present invention is achieved in that the preparation method of described chromone compounds is, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, is specially:
A, medicinal extract extract: get tobacco rhizome, be crushed to 20 ~ 40 orders, with 90 ~ 99% ethanol ultrasonic extraction 3 ~ 5 times, and each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract 160 ~ 200 order silica gel dry column-packings of 4 ~ 5 times amount carry out silica gel column chromatography; Be that the chloroform-acetone solution of 1:0 ~ 1:2 carries out gradient elution with volume proportion, merge identical part, collect each several part elutriant and concentrated;
C, high pressure liquid chromatography are separated: namely the 8:2 part of step B elutriant obtains described chromone compounds with high pressure liquid chromatography separation and purification further.
The structure of the chromone compounds prepared with aforesaid method measures out by the following method:
The compounds of this invention is yellow jelly; UV spectrum (solvent is methyl alcohol),
λ max(log ε) 210 (4.26), 253 (3.68), 292 (3.47) nm; Infrared spectra (pressing potassium bromide troche) ν
max3436,2918,2860,1705,1642,1604,1570,1465,1385,1205,1142,970,863 cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak 245.0819 [M-H]
-(calculated value 245.0814).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
14h
14o
4, degree of unsaturation is 8.From
1h and
13cNMR composes (attribution data is in Table-1) signal and can find out: have 8 aromatic series carbon (δ in compound
c144.3 s, 111.1 d, 160.8 s, 113.5 s, 164.6 s, 114.8 d, 128.0 d, 154.1 s), 2 carbonyl carbon (δ
c193.5 s and 205.9 s), 2 methyl carbon (δ
c22.1 q and 30.5 q), 2 methyl carbon (δ
c72.0 t and 50.2 t).Containing 3 groups of aromatic series hydrogen signal (δ in its hydrogen spectrum
h6.50 (d) 1.8,6.62 (d) 1.8 and 6.29 s), 2 methyl singlets (δ
h2.01 s and 2.44 s), 2 methylene singlets (δ
h4.11 s and 4.42 s), 1 phenolic hydroxyl group (δ
h9.88 s).These signals show to include 1 chromone parent in compound, 1 acetonyl, and 1 phenolic hydroxyl group.From H-8 (δ
h6.29) and C-4 (δ
c113.5), C-7 (δ
c193.5), C-10 (δ
c72.0), C-11 (δ
c22.1), H-10 (δ
h4.42) and C-3 (δ
c160.8), C-8 (δ
c128.0), H-11 (δ
h2.01) and C-8 (δ
c128.0), C-9 (δ
c154.1), C-10 (δ
c72.0) HMBC relevant (accompanying drawing 3) also susceptible of proof has chromone parent to exist.From H-1 ' (δ
h4.11) and C-1 (δ
c144.3), C-2 (δ
c111.1), C-6 (δ
c114.8) the susceptible of proof acetonyl of being correlated with of HMBC, is substituted in the C-1 position of chromone parent. in addition, from phenolic hydroxyl group signal (
δ h9.88) be substituted in C-5 position with the HMBC relevant confirmation phenolic hydroxyl group of C-4 (113.5), C-5 (164.6), C-6 (114.8), so far the structure of compound is confirmed.
table-1. compounds
1
h NMR and
13
c NMR data (CDCl
3
)
| No. | δ C (m) | δ H (m, J, Hz) | No. | δ C (m) | δ H (m, J, Hz) |
| 1 | 144.3 s | ? | 9 | 154.1 s | ? |
| 2 | 111.1 d | 6.50 (d) 1.8 | 10 | 72.0 t | 4.42 s |
| 3 | 160.8 s | ? | 11 | 22.1 q | 2.01 s |
| 4 | 113.5 s | ? | 1' | 50.2 t | 4.11 s |
| 5 | 164.6 s | ? | 2' | 205.9 s | ? |
| 6 | 114.8 d | 6.62 (d) 1.8 | 3' | 30.5 q | 2.44 s |
| 7 | 193.5 s | ? | 5-OH | ? | 9.88 s |
| 8 | 128.0 d | 6.29 s | ? | ? | ? |
The third object of the present invention is achieved in that the preparation be applied to by described chromone compounds in Tobacco mosaic medicine.
Chromone compounds of the present invention is separated first, is determined as chromone compounds by nucleus magnetic resonance and measuring method of mass spectrum, and characterizes its concrete structure.Through the experiment to resisting tobacco mosaic virus, its relative inhibition reaches 25.2%, has good activity of resisting tobacco mosaic virus, and its activity is close to the relative inhibition (28.7%) of reference substance Nanning mycin.Above result discloses compound of the present invention preparing in resisting tobacco mosaic virus medicine good application prospect.The compounds of this invention structure is simple active good, can be used as the guiding compound of resisting tobacco mosaic virus medicine.
Accompanying drawing explanation
Fig. 1 is the carbon-13 nmr spectra of compound;
Fig. 2 is the proton nmr spectra of compound;
Fig. 3 is that the main HMBC of compound is correlated with.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is further illustrated, but limited the present invention never in any form, and any conversion done based on training centre of the present invention or improvement, all fall into protection scope of the present invention.
* except as otherwise noted, the percentage ratio adopted in the present invention is mass percent.
Chromone compounds C of the present invention
14h
13o
4preparation method comprise medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, specifically comprise:
A, medicinal extract extract: get tobacco rhizome, be crushed to 20 ~ 40 orders, with 90 ~ 99% ethanol ultrasonic extraction 3 ~ 5 times, and each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract 160 ~ 200 order silica gel dry column-packings of 4 ~ 5 times amount carry out silica gel column chromatography; Be that the chloroform-acetone solution of 1:0 ~ 1:2 carries out gradient elution with volume proportion, merge identical part, collect each several part elutriant and concentrated;
C, high pressure liquid chromatography are separated: namely the 8:2 part of step B elutriant obtains described chromone compounds with high pressure liquid chromatography separation and purification further.
The etoh solvent concentration of described step A is 95%.
The medicinal extract of described step B before silica gel column chromatography rough segmentation, with after the pure dissolve with methanol of weight ratio 1.5 ~ 3 times amount with 80 ~ 100 order silica gel mixed samples of 1.5 ~ 2.5 times.
The chloroform-acetone solution volume proportion of described step B is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2.
High performance liquid chromatography separation and purification in described step C is employing 21.2 mm × 250 mm, the C of 5 μm
18chromatographic column, flow velocity is 20 mL/min, and moving phase is the methyl alcohol of 50%, and UV-detector determined wavelength is 254 nm, and each sample introduction 200 μ L, collects the chromatographic peak of 18.6 min, repeatedly cumulative rear evaporate to dryness.
Material after the separation and purification of described step C mesohigh liquid phase chromatography uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated with gel filtration chromatography, with further separation and purification.
Chromone compounds of the present invention is preparing the application in resisting tobacco mosaic virus medicine.
The present invention is raw materials used not to be limited by area and kind, and all can realize the present invention, to derive from the tobacco rhizome sample of Yunnan Yuxi, the present invention will be further described below:
embodiment 1
Tobacco rhizome sample source is in Yunnan Yuxi, and kind is cloud and mist-85.Tobacco rhizome is sampled 2.2 kg and be crushed to 30 orders, the supersound extraction 3 times of the ethanol with 95%, extract 30 min at every turn, extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 105.4 g.With the thick silica gel mixed sample of 100 order of 160 g after the pure dissolve with methanol of medicinal extract weight ratio 1.5 times amount, the 160 order silica gel dress posts of 1.0 kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 8:2, methyl alcohol with 50% is moving phase, Zorbax SB-C18 (21.2 × 250 mm, 5 μm) preparative column is stationary phase, flow velocity is 20 ml/min, UV-detector determined wavelength is 254 nm, each sample introduction 200 μ L, collect the chromatographic peak of 18.6 min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-20 gel filtration chromatography.
embodiment 2
Tobacco rhizome sample source is in Yunnan Yuxi, and kind is cloud and mist-85.Tobacco rhizome is sampled 3.5 kg and be crushed to 40 orders, the supersound extraction 5 times of the ethanol with 90%, extract 45 min at every turn, extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 215 g.With the thick silica gel mixed sample of 80 order of 350 g after the pure dissolve with methanol of medicinal extract weight ratio 3 times amount, the 200 order silica gel dress posts of 1.5 kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 8:2, methyl alcohol with 50% is moving phase, Zorbax SB-C18 (21.2 × 250 mm, 5 μm) preparative column is stationary phase, flow velocity is 20 ml/min, UV-detector determined wavelength is 254nm, each sample introduction 200 μ L, collect the chromatographic peak of 18.6 min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-20 gel filtration chromatography.
embodiment 3
Tobacco rhizome sample source is in Yunnan Yuxi, and kind is cloud and mist-85.Tobacco rhizome is sampled 5 kg and be crushed to 60 orders, the supersound extraction 3 times of the ethanol with 99%, extract 60 min at every turn, extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 312 g.With the thick silica gel mixed sample of 90 order of 500 g after the pure dissolve with methanol of medicinal extract weight ratio 1.6 times amount, the 180 order silica gel dress posts of 1.8 kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 8:2, methyl alcohol with 50% is moving phase, Zorbax SB-C18 (21.2 × 250 mm, 5 μm) preparative column is stationary phase, flow velocity is 20 ml/min, UV-detector determined wavelength is 254 nm, each sample introduction 200 μ L, collect the chromatographic peak of 18.6 min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-20 gel filtration chromatography.
embodiment 4
Compound prepared by Example 1 is yellow jelly.
Measuring method is: with nucleus magnetic resonance, in conjunction with other spectroscopic technique qualification structure.
1) UV spectrum (solvent is methyl alcohol), λ max (log ε) 210 (4.26), 253 (3.68), 292 (3.47) nm;
2) infrared spectra (pressing potassium bromide troche) ν max 3436,2918,2860,1705,1642,1604,1570,1465,1385,1205,1142,970,863 cm-1;
3) high resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak 245.0819 [M-H]
-(calculated value 245.0814).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
14h
14o
4, degree of unsaturation is 8.
From
1h and
13cNMR composes (attribution data is in Table-1) signal and can find out: have 8 aromatic series carbon (δ in compound
c144.3 s, 111.1 d, 160.8 s, 113.5 s, 164.6 s, 114.8 d, 128.0 d, 154.1 s), 2 carbonyl carbon (δ
c193.5 s and 205.9 s), 2 methyl carbon (δ
c22.1 q and 30.5 q), 2 methyl carbon (δ
c72.0 t and 50.2 t).Containing 3 groups of aromatic series hydrogen signal (δ in its hydrogen spectrum
h6.50 (d) 1.8,6.62 (d) 1.8 and 6.29 s), 2 methyl singlets (δ
h2.01 s and 2.44 s), 2 methylene singlets (δ
h4.11 s and 4.42 s), 1 phenolic hydroxyl group (δ
h9.88 s).These signals show to include 1 chromone parent in compound, 1 acetonyl, and 1 phenolic hydroxyl group.From H-8 (δ
h6.29) and C-4 (δ
c113.5), C-7 (δ
c193.5), C-10 (δ
c72.0), C-11 (δ
c22.1), H-10 (δ
h4.42) and C-3 (δ
c160.8), C-8 (δ
c128.0), H-11 (δ
h2.01) and C-8 (δ
c128.0), C-9 (δ
c154.1), C-10 (δ
c72.0) HMBC relevant (accompanying drawing 3) also susceptible of proof has chromone parent to exist.From H-1 ' (δ
h4.11) and C-1 (δ
c144.3), C-2 (δ
c111.1), C-6 (δ
c114.8) the susceptible of proof acetonyl of being correlated with of HMBC, is substituted in the C-1 position of chromone parent. in addition, from phenolic hydroxyl group signal (
δ h9.88) be substituted in C-5 position with the HMBC relevant confirmation phenolic hydroxyl group of C-4 (113.5), C-5 (164.6), C-6 (114.8), so far the structure of compound is confirmed.
embodiment 5
Compound prepared by Example 2 is yellow jelly.Measuring method is identical with embodiment 4, confirms that compound prepared by embodiment 2 is described chromone compounds---tobacco chromone C.
embodiment 6
Compound prepared by Example 3 is yellow jelly.Measuring method is identical with embodiment 4, confirms that compound prepared by embodiment 3 is described chromone compounds---tobacco chromone C.
embodiment 7
Arbitrary chromone compounds prepared by Example 1 ~ 3 carries out activity of resisting tobacco mosaic virus test, and test situation is as follows:
Adopt half leaf method, when the mass concentration of medicament is 50 mg/L, activity of resisting tobacco mosaic virus mensuration is carried out to the compounds of this invention.5 ~ 6 age flue-cured tobacco plant on, choose the blade (leaf capable normal, anosis without worm) being applicable to test, first blade evenly sprinkled fine emery powder, with writing brush by tobacco mosaic virus (TMV) source (3.0 × 10 for subsequent use
-3) be evenly put on sprinkled with silicon carbide blade on, connect after poison terminates until the blade of all middle choosings, be placed on immediately in the culture dish filling liquid and process 20 min, take out, to spill on defoliation sheet the globule and about liquid, two and half leaves are restored and is emitted on the enamel son of an influential official cover glass being covered with toilet paper moisturizing, temperature control (23 ± 2) DEG C, be placed on greenhouse natural light irradiation, within 2 ~ 3 days, be visible withered spot. each process sets second half leaf as contrast, be provided with in addition 1 group be the process of commodity Ningnanmycin as a comparison, press formulae discovery relative inhibition.
XI％=(CK-T)／CK×100％
X: relative inhibition (%), CK: be soaked in the withered spot number (individual) that half in clear water connects malicious leaf, T is soaked in the withered spot number (individual) that half in liquid connects malicious leaf.
The relative inhibition of result bright compound is 25.2%, and the relative inhibition 28.7% of contrast Ningnanmycin is close, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (8)
1. a chromone compounds, it is characterized in that described compound is separated to obtain from tobacco rhizome, its molecular formula is C
14h
13o
4, there is following structure:
。
2. a preparation method for chromone compounds according to claim 1, is characterized in that taking tobacco rhizome as raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, is specially:
A, medicinal extract extract: get tobacco rhizome, be crushed to 20 ~ 40 orders, with 90 ~ 99% ethanol ultrasonic extraction 3 ~ 5 times, and each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract 160 ~ 200 order silica gel dry column-packings of 4 ~ 5 times amount carry out silica gel column chromatography; Be that the chloroform-acetone solution of 1:0 ~ 1:2 carries out gradient elution with volume proportion, merge identical part, collect each several part elutriant and concentrated;
C, high pressure liquid chromatography are separated: namely the 8:2 part of step B elutriant obtains described chromone compounds with high pressure liquid chromatography separation and purification further.
3. the preparation method of chromone compounds as claimed in claim 2, is characterized in that the alcohol concn in described step A is 95%.
4. the preparation method of chromone compounds as claimed in claim 2, is characterized in that in described step B, medicinal extract is before silica gel column chromatography rough segmentation, with 80 ~ 100 order silica gel mixed samples after the pure dissolve with methanol of weight ratio 1.5 ~ 3 times amount by weight ratio being 1.5 ~ 2.5 times.
5. the preparation method of chromone compounds as claimed in claim 2, is characterized in that the chloroform-acetone solution volume proportion in described step B is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2.
6. the preparation method of chromone compounds as claimed in claim 2, is characterized in that the separation and purification of described step C mesohigh liquid phase chromatography is employing 21.2 mm × 250 mm, the C of 5 μm
18chromatographic column, flow velocity is 20 mL/min, and moving phase is the methyl alcohol of 50%, and UV-detector determined wavelength is 254 nm, and each sample introduction 200 μ L, collects the chromatographic peak of 18.6 min, repeatedly cumulative rear evaporate to dryness.
7. the preparation method of chromone compounds as claimed in claim 2, it is characterized in that the material after the separation and purification of described step C mesohigh liquid phase chromatography uses pure dissolve with methanol again, again with pure methyl alcohol for moving phase, with gel filtration chromatography be separated, with further separation and purification.
8. a chromone compounds according to claim 1 is preparing the application in resisting tobacco mosaic virus medicine.
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| CN104370726B (en) * | 2014-08-06 | 2016-02-24 | 云南中烟工业有限责任公司 | A kind of biphenyl compound with isohexyl side chain and its preparation method and application |
| CN104370874B (en) * | 2014-08-06 | 2016-05-25 | 云南中烟工业有限责任公司 | A kind of parallel heptatomic ring biphenyl compound and its preparation method and application |
| CN109438406B (en) * | 2018-11-19 | 2021-10-22 | 云南中烟工业有限责任公司 | Chromone derivative extracted from anshansenia glauca and preparation method and application thereof |
| CN109574973B (en) * | 2018-11-19 | 2021-11-26 | 云南中烟工业有限责任公司 | Chromone derivative in anshansenna and preparation method and application thereof |
| CN109265423A (en) * | 2018-11-20 | 2019-01-25 | 云南民族大学 | A kind of chromone compounds and its preparation method and application |
| CN114685524B (en) * | 2022-04-12 | 2023-07-14 | 云南中烟工业有限责任公司 | Chromone compound and preparation method and application thereof |
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| DE2931399A1 (en) * | 1979-08-02 | 1981-02-26 | Kali Chemie Pharma Gmbh | NEW 3-AMINO-1-BENZOXEPINE DERIVATIVES AND THEIR SALTS, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| DE3440295A1 (en) * | 1984-11-05 | 1986-05-15 | Kali-Chemie Pharma Gmbh, 3000 Hannover | METHOD FOR DIASTEREOSELECTIVE REDUCTION OF 3-AMINO-1-BENZOXEPIN-5 (2H) -ONES |
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