CN106588949A - Artemisinin ester compound with cardiovascular and cerebrovascular disease prevention and treatment activity and preparation method and application of artemisinin ester compound - Google Patents
Artemisinin ester compound with cardiovascular and cerebrovascular disease prevention and treatment activity and preparation method and application of artemisinin ester compound Download PDFInfo
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- CN106588949A CN106588949A CN201611128178.XA CN201611128178A CN106588949A CN 106588949 A CN106588949 A CN 106588949A CN 201611128178 A CN201611128178 A CN 201611128178A CN 106588949 A CN106588949 A CN 106588949A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/20—Spiro-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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Abstract
The invention discloses an artemisinin ester compound which has cardiovascular and cerebrovascular disease prevention and treatment activity after proof. The artemisinin ester compound has the following general molecular formula (please see the specification), and the general chemical formula of the artemisinin ester compound is (3R, 5aS, 6R, 8aS, 9R, 12S, 12aR)-octahydro-3-[N-(alpha-R1)R2 disulfo formyl]methylene-6,9-dimethyl-3,12-bridging oxygen-12H-pyrano [4,3-j]-1,2-benzo dithi prienzepine-10(3H)alcohol. The compound has the remarkable functions of reducing blood sugar and blood fat, a cardiovascular and cerebrovascular vessel prevention and treatment new drug with important practical value is expected to be formed, and the application range and development direction of relevant drugs are expanded.
Description
Technical field
The present invention relates to a kind of compound with pharmaceutical active, especially a kind of to have cardiovascular disease prevention activity
Compound.
Background technology
Arteannuin is yellow from feverfew first in 1971 by cry of a deer Research Team as representative is slaughtered with China scientist
A kind of Sesquiterpene lactones compound with peroxide bridge construction being separated to is extracted in flower mugwort, and is applied to subtertian malaria
The treatment of disease.In decades, in order to reach improve the drug effect of arteannuin, water solublity, it is fat-soluble or lifted its bioavailability,
Extend the purposes such as its half-life, people have carried out the improvement of series and derivative to arteannuin, have developed substantial amounts of semi-synthetic spread out
Biology, for example:Dihydroartemisinine, Artemether, arteether, artesunate etc..
Find in the long-term model test and clinical practice of medicine, in addition to antimalarial active, these artificial improvement
Compound also there is otherwise activity sometimes, and be expected to be formed the medicament research and development with important practical value and using new
Direction.
The content of the invention
The technical problem to be solved in the present invention is to provide the Herba Artemisiae Annuae that a kind of empirical tests have cardiovascular disease prevention activity
Plain ester type compound.
To solve above-mentioned technical problem, the technical solution used in the present invention is as follows：
A kind of arteannuin ester type compound with cardiovascular disease prevention activity, the general structure of the compound
For：
Used as a preferred technical solution of the present invention, the compound is for concrete chemical general formula：(3R,5aS,6R,
8aS, 9R, 12S, 12aR)-octahydro -3- [N-(α-R1)R2Dithiocarbonic acid base] methylene -6,9- dimethyl -3,12- bridging oxygens -
Simultaneously the thiophene of [4,3-j] -1,2- benzos two puts down -10 (3H) alcohol to 12H- pyrans.
As a preferred technical solution of the present invention, the R1For methoxycarbonyl group.
As a preferred technical solution of the present invention, the R1For carboxyl.
As a preferred technical solution of the present invention, the R2For methylamino.
As a preferred technical solution of the present invention, the R2For benzene ethylamino.
As a preferred technical solution of the present invention, the R1For methoxycarbonyl group and the R2For methylamino.
As a preferred technical solution of the present invention, the R1For carboxyl and the R2For benzene ethylamino.
The preparation technology of the above-mentioned arteannuin ester type compound with cardiovascular disease prevention activity, its route flow process
For：
Wherein, the reaction dissolvent is using N,N-Dimethylformamide or alcohol organic solvent.
The above-mentioned arteannuin ester type compound with cardiovascular disease prevention activity is used to prepare cardiovascular and cerebrovascular disease phase
Close medicine.
It is using the beneficial effect produced by above-mentioned technical proposal：The research team of applicant is in artemisinin derivative medicine
Find in the long-term model test of thing and clinical practice, in addition to antimalarial active, these artificial improved compounds are sometimes
Also there is otherwise activity, based on this, applicant has carried out series of experiments checking to some artemisinin derivatives, and from
In be found that the compound with notable blood sugar lowering, blood fat reducing effectiveness mentioned above, be expected to be formed with important practical value
Cardiovascular and cerebrovascular vessel preventing and treating new drug, and expand the range of application and R＆D direction of related drugs.
Specific embodiment
Following examples are described in detail the present invention.Various raw materials used in the present invention and items of equipment are conventional city
Product is sold, can be directly obtained by market purchase.
Embodiment 1
Prepare compound：(3R, 5aS, 6R, 8aS, 9R, 12S, 12aR)-octahydro -3- [N-(α-methoxycarbonyl group) methylamino two
Bamic acid base] methylene -6,9- dimethyl -3, simultaneously the thiophene of [4,3-j] -1,2- benzos two puts down -10 to 12- bridging oxygen -12H- pyrans
(3H) alcohol.The structural formula of the compound is：
Preparation technology flow process：To in reactor add 3.62g (0.01mol) (3R, 5aS, 6R, 8aS, 9R, 12S,
12aR)-octahydro -3- bromines methylene -6,9- dimethyl -3, simultaneously the thiophene of [4,3-j] -1,2- benzos two puts down -1 to 12- bridging oxygen -12H- pyrans
(3H) alcohol and 25mL DMF, stirring adds N- (α-methoxycarbonyl group) the methylamino dithiocarbonic acid of 2.24g (0.012mol)
Sodium, reacts 12 hours, and decompression steams solvent；Residue adds 20mL ethyl acetate and 20mL water, stirring, layering, water layer acetic acid
Ethyl ester is extracted, and merges organic faciess, is dried, and is filtered, and concentration, column chromatography purification obtains purpose compound：(3R,5aS,6R,8aS,9R,
12S, 12aR)-octahydro -3- [N-(α-methoxycarbonyl group) methylamino dithiocarbamate formyl] methylene -6,9- dimethyl -3,12- bridges
Simultaneously the thiophene of [4,3-j] -1,2- benzos two puts down -10 (3H) alcohol to oxygen -12H- pyrans, and yield 77.7% experiment proves that, with good
The preventing and treating of the cardiovascular and cerebrovascular disease such as blood fat reducing, blood sugar lowering is active (referring to embodiment 3).
Embodiment 2
Prepare compound：(3R, 5aS, 6R, 8aS, 9R, 12S, 12aR)-octahydro -3- [N-(α-carboxyl) sulfur of benzene ethylamino two
Acute pyogenic infection of nails acidic group] methylene -6,9- dimethyl -3, simultaneously the thiophene of [4,3-j] -1,2- benzos two puts down -10 (3H) to 12- bridging oxygen -12H- pyrans
Alcohol.The structural formula of the compound is：
Preparation technology flow process：To in reactor add 3.62g (0.01mol) (3R, 5aS, 6R, 8aS, 9R, 12S,
12aR)-octahydro -3- bromines methylene -6,9- dimethyl -3, simultaneously the thiophene of [4,3-j] -1,2- benzos two puts down -1 to 12- bridging oxygen -12H- pyrans
(3H) alcohol and 25mL DMF, stirring adds 3.32g (0.012mol) N-(α-methoxycarbonyl group) PhenethyIamino dithiocarbonic acid
Sodium, reacts 12 hours, and decompression steams solvent；Residue adds 20mL ethyl acetate and 20mL water, stirring, layering, water layer acetic acid
Ethyl ester is extracted, and merges organic faciess, is dried, and is filtered, and concentration, column chromatography purification obtains intermediate compound；Take 5.37g (0.01mol)
Gained intermediate compound, adds methanol 15mL and 1molL-1NaOH solution 12mL, be stirred at room temperature 1 hour, steam solvent, instead
Answer liquid 1molL-1HCl solution 3-4mL adjust pH=2, add 15mL ethyl acetate, stirring, layering, aqueous layer with ethyl acetate
Extract, merge organic faciess, be dried, filter, concentration, column chromatography purification obtains purpose compound：(3R,5aS,6R,8aS,9R,12S,
12aR)-octahydro -3- [N-(α-carboxyl) benzene ethylamino dithiocarbonic acid base] methylene -6,9- dimethyl -3,12- bridging oxygen -12H-
Pyrans simultaneously flat -10 (3H) alcohol of the thiophene of [4,3-j] -1,2- benzos two, yield 65.1% experiment proves that, with good blood fat reducing,
The preventing and treating of the cardiovascular and cerebrovascular disease such as blood sugar lowering is active (referring to embodiment 3).
The pharmaceutical active test of embodiment 3, purpose compound
Experimental animal rat is provided by Medical School of Zhengzhou University.Key instrument and reagent are conventional commercial product.
Take normal SPF levels male SD rat 10 and be only used as Normal group, measurement fasting glucose and body weight, daily injection is poly-
Glycol water (1mgKg-1) continue 30 days；
10 diabetic model rats are taken as test control group, measurement fasting glucose and body weight, poly- second two is injected daily
Alcohol-water solution (1mgKg-1) continue 30 days；
10 diabetic model rats are taken as test of cure group A, measurement fasting glucose and body weight, daily intramuscular injection reality
Apply the compound water solution (1mgKg of the preparation of example 1-1) continue 30 days；
10 diabetic model rats are taken as test of cure group B, measurement fasting glucose and body weight, daily intramuscular injection reality
Apply the compound water solution (1mgKg of the preparation of example 2-1) continue 30 days；
10 diabetic model rats are taken as test of cure group AB, measurement fasting glucose and body weight, muscle respectively daily
Compound water solution (difference 0.5mgKg prepared by injection embodiment 1,2-1) continue 30 days；
Last rat tail takes tail vein 2mL, and using blood glucose meter blood sugar detection is carried out, while rat body weight is weighed, knot
It is really as shown in the table：
In addition, after process terminates the lipids contents of each group rat are determined using Cholesterol Kit, as a result
It is as shown in the table：
It can be seen that compound injection liquid prepared by embodiment 1,2 is respectively provided with blood sugar lowering, blood fat reducing and maintenance rat body weight
Fairly obvious effect (p ＜ 0.01), is expected to develop the preventing and treating for diabetes related diseases or adjuvant drug.
Foregoing description is only proposed as enforceable technical scheme of the invention, not as to the single of its technical scheme itself
Restrictive condition.
Claims (10)
1. it is a kind of with cardiovascular disease prevention activity arteannuin ester type compound, it is characterised in that：The compound
General structure is：
2. the arteannuin ester type compound with cardiovascular disease prevention activity according to claim 1, its feature exists
In：The compound is for concrete chemical general formula：(3R, 5aS, 6R, 8aS, 9R, 12S, 12aR)-octahydro -3- [N-(α-R1)R2Two
Bamic acid base] methylene -6,9- dimethyl -3, simultaneously the thiophene of [4,3-j] -1,2- benzos two puts down -10 to 12- bridging oxygen -12H- pyrans
(3H) alcohol.
3. the arteannuin ester type compound with cardiovascular disease prevention activity according to claim 2, its feature exists
In：The R1For methoxycarbonyl group.
4. the arteannuin ester type compound with cardiovascular disease prevention activity according to claim 2, its feature exists
In：The R1For carboxyl.
5. the arteannuin ester type compound with cardiovascular disease prevention activity according to claim 2, its feature exists
In：The R2For methylamino.
6. the arteannuin ester type compound with cardiovascular disease prevention activity according to claim 2, its feature exists
In：The R2For benzene ethylamino.
7. the arteannuin ester type compound with cardiovascular disease prevention activity according to claim 2, its feature exists
In：The R1For methoxycarbonyl group and the R2For methylamino.
8. the arteannuin ester type compound with cardiovascular disease prevention activity according to claim 2, its feature exists
In：The R1For carboxyl and the R2For benzene ethylamino.
9. described in claim 1 with cardiovascular disease prevention activity arteannuin ester type compound preparation technology, its
It is characterised by：The route flow process of the preparation technology is：
Wherein, the reaction dissolvent is using N,N-Dimethylformamide or alcohol organic solvent.
10. described in claim 1 with cardiovascular disease prevention activity arteannuin ester type compound purposes, its feature
It is：The purposes is to prepare cardiovascular and cerebrovascular disease related drugs.
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| CN201810162468.9A CN108383851A (en) | 2016-12-09 | 2016-12-09 | One kind having the active qinghaosu ester type compound of cardiovascular disease prevention, preparation method and its application |
| CN201810118146.4A CN108341829B (en) | 2016-12-09 | 2016-12-09 | Artemisinin ester compound with cardiovascular and cerebrovascular disease prevention and treatment activity, preparation method and application thereof |
| CN201611128178.XA CN106588949B (en) | 2016-12-09 | 2016-12-09 | A kind of qinghaosu ester type compound, its preparation method and its application with cardiovascular disease prevention activity |
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| CN201810118146.4A Division CN108341829B (en) | 2016-12-09 | 2016-12-09 | Artemisinin ester compound with cardiovascular and cerebrovascular disease prevention and treatment activity, preparation method and application thereof |
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| CN201611128178.XA Active CN106588949B (en) | 2016-12-09 | 2016-12-09 | A kind of qinghaosu ester type compound, its preparation method and its application with cardiovascular disease prevention activity |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110483545A (en) * | 2019-08-28 | 2019-11-22 | 西南大学 | Dihydroartemisinine phenol derivatives containing oxime, synthetic method and application |
| CN110483546A (en) * | 2019-08-28 | 2019-11-22 | 西南大学 | Dihydroartemisinine sulphonamide derivatives, synthetic method and application |
| CN110563744A (en) * | 2019-10-10 | 2019-12-13 | 田辉 | Compound for preventing and controlling noctuids in gardens and application |
| CN116120337A (en) * | 2021-05-11 | 2023-05-16 | 中国人民解放军陆军军医大学第一附属医院 | Dihydroartemisinin derivative, medicine and application thereof in preparation of medicine for preventing and treating cerebrovascular diseases |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108383851A (en) * | 2016-12-09 | 2018-08-10 | 新乡学院 | One kind having the active qinghaosu ester type compound of cardiovascular disease prevention, preparation method and its application |
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| CN104892633A (en) * | 2015-05-29 | 2015-09-09 | 石家庄学院 | Dihydroartemisinin dithiocarbamate as well as preparation method and application of dihydroartemisinin dithiocarbamate |
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| CN101879158B (en) * | 2010-07-01 | 2012-02-29 | 中国科学院广州生物医药与健康研究院 | New application of artemisinin derivant |
| CN104398505B (en) * | 2013-04-10 | 2017-06-13 | 上海交通大学 | Artemisine compounds are preparing the purposes in treating and preventing high blood cholesterol drug |
| CN103230392A (en) * | 2013-04-10 | 2013-08-07 | 上海交通大学 | Purposes of artemisinin compounds in preparing anti-atherosclerotic medicaments |
| EP2929881A1 (en) * | 2014-04-11 | 2015-10-14 | CeMM - Forschungszentrum für Molekulare Medizin GmbH | Medical use of artemisinin compounds and gephyrin agonists |
| CN108383851A (en) * | 2016-12-09 | 2018-08-10 | 新乡学院 | One kind having the active qinghaosu ester type compound of cardiovascular disease prevention, preparation method and its application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104892633A (en) * | 2015-05-29 | 2015-09-09 | 石家庄学院 | Dihydroartemisinin dithiocarbamate as well as preparation method and application of dihydroartemisinin dithiocarbamate |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110483545A (en) * | 2019-08-28 | 2019-11-22 | 西南大学 | Dihydroartemisinine phenol derivatives containing oxime, synthetic method and application |
| CN110483546A (en) * | 2019-08-28 | 2019-11-22 | 西南大学 | Dihydroartemisinine sulphonamide derivatives, synthetic method and application |
| CN110483546B (en) * | 2019-08-28 | 2022-08-12 | 西南大学 | Dihydroartemisinin sulfanilamide derivative, synthesis method and application |
| CN110483545B (en) * | 2019-08-28 | 2022-08-16 | 西南大学 | Dihydroartemisinin oxime-containing phenol derivative, and synthesis method and application thereof |
| CN110563744A (en) * | 2019-10-10 | 2019-12-13 | 田辉 | Compound for preventing and controlling noctuids in gardens and application |
| CN116120337A (en) * | 2021-05-11 | 2023-05-16 | 中国人民解放军陆军军医大学第一附属医院 | Dihydroartemisinin derivative, medicine and application thereof in preparation of medicine for preventing and treating cerebrovascular diseases |
| CN116120337B (en) * | 2021-05-11 | 2023-08-25 | 中国人民解放军陆军军医大学第一附属医院 | Dihydroartemisinin derivative, medicine and application thereof in preparation of medicine for preventing and treating cerebrovascular diseases |
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| CN108341829B (en) | 2020-01-24 |
| CN106588949B (en) | 2018-03-30 |
| CN108383851A (en) | 2018-08-10 |
| CN108341829A (en) | 2018-07-31 |
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Effective date of registration: 20190710 Address after: 453000 Qiliying Industrial Park, Xinxiang County, Xinxiang City, Henan Province Patentee after: Henan Green Garden Pharmaceutical Co., Ltd. Address before: No. 191 Jinsui Avenue, Xinxiang City, Henan Province, 453003 Patentee before: Xinxiang University |
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