CN1439628A - Ferulaic acid esters and preparation and application thereof - Google Patents
Ferulaic acid esters and preparation and application thereof Download PDFInfo
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- CN1439628A CN1439628A CN 03109056 CN03109056A CN1439628A CN 1439628 A CN1439628 A CN 1439628A CN 03109056 CN03109056 CN 03109056 CN 03109056 A CN03109056 A CN 03109056A CN 1439628 A CN1439628 A CN 1439628A
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Abstract
A ferulate compound and its preparing process are disclosed. Said ferulate compound can play the role of preventing and treating thrombus and decreasing blood fat, so it can be used as the medicine for preventing cerebothrombus and hyperlipemia (high triglyceride). Its advantages are high activity and low toxic by-effect.
Description
Technical field
The effective constituent that the present invention relates to a kind of Chinese medicine (Radix Angelicae Sinensis, Ligusticum wallichii etc.) is through the new chemical structure-ferulic acid ester of structure of modification synthetic, and relates to and its production and application.
Background technology
Thrombus is one of Hazard Factor of cardiovascular and cerebrovascular diseases.The formation of thrombus and arachidonic meta-bolites are in close relations, and the tissue ischemia that hematoblastic adhesion and gathering and microcirculation disturbance cause also is relevant with the generation of vascular lesion.In recent years, about TXA
2/ PGI
2Balance adjustment carried out comparatively systematic research.Forulic acid is one of effective constituent in the Chinese medicine (Radix Angelicae Sinensis, Ligusticum wallichii etc.).Forulic acid anticoagulant and release action may with suppress TXA
2Generation relevant, be the concentration dependence.Thrombocyte synthesizes PGE simultaneously
2And PGF
2aCorresponding minimizing illustrates that this compound suppresses thrombocyte epoxidase activity.Forulic acid obviously suppresses the formation of experimental thrombosis, suppresses gathering of ADP and collagen-induced platelet and 5-HT and discharges from thrombocyte.Therefore forulic acid has the thrombosis of inhibition, regulates effects such as body's immunity, removing and inhibition free radical reaction, proves that this compound can shield by the 26S Proteasome Structure and Function of number of ways to biomacromolecule in the body.
Summary of the invention
The objective of the invention is to: forulic acid is synthesized the brand-new ester class chemical structure with pharmaceutical use, i.e. a ferulic acid ester compound through the structure of modification screening.
Another object of the present invention provides a kind of preparation method of ferulic acid ester compound of the present invention.
Another object of the present invention is the application of ferulic acid ester compound in antithrombotic or reducing blood lipid.
The general formula of ferulic acid ester compound of the present invention (I) is:
Wherein R1=contains carboxylic acid group's the chemical structure with antithrombotic or blood fat reducing function;
R2=hydrogen base, sodium, potassium, various alkyl.
Above-mentioned R1 is Asprin, Chlorophibrinic Acid, to the chlorobenzoyl Bezalip Tablets, to one of benzyl chloride oxygen isovaleric acid, Win-35833, gemfibrozil etc.
Above-mentioned R2 is hydrogen base, sodium, potassium or alkyl, i.e. hydrogen base, methyl, ethyl, chain hydrocarbon or cyclic hydrocarbon radical etc.
The preparation method of ferulic acid ester compound of the present invention is:
In reaction flask, add the acid compound of above-claimed cpd R1, add acetone solution, add sulfur oxychloride, under 0-10 ℃ of condition, stirred 2-24 hour, add the basic solution of 3-methoxyl group-4-Hydroxycinnamic Acid again, reaction got product in 2-24 hour under the pyridine catalytic condition, and is standby; Again in said vesse, add acetone solution, add sodium hydroxide or sodium hydrogen carbonate solution simultaneously, add sulfur oxychloride, add sulfur oxychloride and under 0-10 ℃ of condition, reacted 2-8 hour, add the alkyl of hydroxy-containing compounds or the basic solution of alkyl again, under pyridine catalysis, reacted 2-24 hour, and made ferulic acid ester compound of the present invention.
The inventor finds that ferulic acid ester compound of the present invention has the effect of antithrombotic, reducing blood-fat.
Active ingredient of Chinese herbs forulic acid (3-methoxyl group-4-Hydroxycinnamic Acid) and antithrombotic or reducing blood-fat chemicals are combined, make the brand-new medicine of new antithrombotic, reducing blood-fat.Can improve the activity intensity of active ingredient of Chinese herbs, reduce the poison of chemicals, pay effect, start from a novel method of the new medicine of active skull cap components screening.Ferulic acid ester compound of the present invention has unique pharmacologically active, active strong, both but antithrombotic also can reducing blood-fat, main pharmacology mechanism is anticoagulant and suppresses the synthetic of cholesterol and triglyceride level, can be used as the generation of prevention of brain thrombus and high triglyceride, as person in middle and old age personnel's prophylactic, market outlook are big.This medicine is the ester class, and the toxic side effect of this medicine is less, can take for a long time.
Embodiment
The present invention is described in detail below in conjunction with embodiment.
This product is 3-methoxyl group-4-substituted oxy TRANSCINNAMIC ACID or hydrochlorate or ester.
Embodiment 1:
When
R2=-H then The compounds of this invention is:
Chemical name: 3-methoxyl group-4[2-(4-chlorophenoxy-2-methylpropionyl) oxygen base TRANSCINNAMIC ACID]
Its preparation method is:
In the reaction flask of reflux is housed, drop into Chlorophibrinic Acid, add acetone solution, add the chlorination sulfoxide, start stirring, splash into pyridine, heating is stirred, and steams excessive sulfur oxychloride, must be to chlorobenzene oxygen isobutyryl chloride.
Drop into forulic acid in reaction flask, under agitation behind the hydro-oxidation sodium liquid, at 0-10 ℃, add chlorobenzene oxygen isobutyryl chloride, reacted 20 hours, neutralization is left standstill, and filters, and gets the product crude product, gets the white crystals elaboration behind the recrystallization.
Embodiment 2:
When
R2=-H is then: The compounds of this invention is:
Chemistry is by name: 3-methoxyl group-4 (2-acetoxy benzoyl) oxygen base TRANSCINNAMIC ACID, the preparation method is with embodiment 1.
Embodiment 3:
When
R2=-H is then: The compounds of this invention is: chemical name: 3-methoxyl group-4[2-(to the chlorobenzoyl phenoxy group)-2-methylpropane] oxygen base TRANSCINNAMIC ACID
Embodiment 4: when
R2=-H is then: The compounds of this invention is:
Chemical name: 3-methoxyl group-4[2-(4-chloro-phenyl-)-4 tolyl oxygen bases-2-methylbutyryl base] oxygen base TRANSCINNAMIC ACID
Embodiment 5: when
R2=-H is then: The compounds of this invention is:
Chemical name: 3-methoxyl group-4[2.2-dimethyl-5-(2.5-dimethyl phenoxy) pentanoyl] oxygen base TRANSCINNAMIC ACID
Embodiment 6: when
R2=-H is then: The compounds of this invention is:
Chemical name: 3-methoxyl group-4[2-(4-(2.2-dichloro cyclopropyl) benzene oxygen)-2-methylpropionyl] oxygen base TRANSCINNAMIC ACID
Embodiment 7: as R1=R2=-CH
3 
Then: The compounds of this invention is:
Chemical name: 3-methoxyl group-4 (2-acetoxy benzoyl) oxygen base Methyl cinnamylate.
Embodiment 8 works as R1=_H
Then: The compounds of this invention is:
Chemical name: 3-methoxyl group-4-Hydroxycinnamic Acid salicylate
Its preparation method is:
In the reaction flask of reflux is housed, add 3-methoxyl group-4-Hydroxycinnamic Acid, stirring is started in the dissolving of hydrogenation sodium-chlor acetone soln, splashes into sulfur oxychloride, on the contrary under 0-10 ℃ of condition 2-8 hour, 3-methoxyl group-4-hydroxyl cassia bark acyl chlorides.
Drop into Whitfield's ointment in reaction flask, under agitation add acetone solution, add pyridine and add 3-methoxyl group-4-hydroxyl cassia bark acyl chlorides at 0-10 ℃, reacted 6 hours, neutralization is left standstill, and filters, and gets the product crude product, gets the white crystals elaboration behind the recrystallization.This product is made tablet or glue assists and is used for antithrombotic, reducing blood-fat.
Embodiment 9:
When
R2=-Na is then: The compounds of this invention is:
Chemistry is by name: 3-methoxyl group-4 (2-acetoxy benzoyl) oxygen base natrium cinnamicum.
Embodiment 2:
Work as R1=
R2=-K is then: The compounds of this invention is:
Chemistry is by name: 3-methoxyl group-4 (2-acetoxy benzoyl) oxygen base TRANSCINNAMIC ACID potassium
Claims (7)
1, a kind of general formula is the ferulic acid ester compound of (I),
In the formula: wherein R1=contains carboxylic acid group's the chemical structure with antithrombotic or blood fat reducing function;
R2=hydrogen base, sodium, potassium, various alkyl.
2, ferulic acid ester compound according to claim 1, wherein: R1 be Asprin, Chlorophibrinic Acid, to the chlorobenzoyl Bezalip Tablets, to benzyl chloride oxygen isovaleric acid, Win-35833, gemfibrozil etc. it
3, ferulic acid ester compound according to claim 1 and 2, R2 is hydrogen base, methyl, ethyl.
4, ferulic acid ester compound according to claim 1 and 2, R2 is sodium, potassium.
5, ferulic acid ester compound according to claim 1 and 2, R2 are the chain hydrocarbon or the cyclic hydrocarbon radical of hydroxyl.
6, the preparation method of ferulic acid ester compound according to claim 1, this method may further comprise the steps: in reaction flask, the acid compound that adds above-claimed cpd R1, add acetone solution, add sulfur oxychloride, under 0-10 ℃ of condition, stirred 2-24 hour, add the basic solution of 3-methoxyl group-4-Hydroxycinnamic Acid again, reaction got product in 2-24 hour under the pyridine catalytic condition, and is standby; Again in said vesse, add acetone solution, add sodium hydroxide or sodium hydrogen carbonate solution simultaneously, add sulfur oxychloride, add sulfur oxychloride and under 0-10 ℃ of condition, reacted 2-8 hour, add the alkyl of hydroxy-containing compounds or the basic solution of alkyl again, under pyridine catalysis, reacted 2-24 hour, and made ferulic acid ester compound of the present invention.
7, each the application of ferulic acid ester compound in antithrombotic or blood lipid-lowering medicine among the claim 1-5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03109056 CN1439628A (en) | 2003-04-03 | 2003-04-03 | Ferulaic acid esters and preparation and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03109056 CN1439628A (en) | 2003-04-03 | 2003-04-03 | Ferulaic acid esters and preparation and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1439628A true CN1439628A (en) | 2003-09-03 |
Family
ID=27796709
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|---|---|---|---|
| CN 03109056 Pending CN1439628A (en) | 2003-04-03 | 2003-04-03 | Ferulaic acid esters and preparation and application thereof |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008062466A3 (en) * | 2006-10-13 | 2008-09-25 | Reliance Life Sciences Pvt Ltd | Cinnamic acid, vanillic acid and benzofuran derivatives for use in the treatment of inflammation and cancer |
| CN100429218C (en) * | 2006-04-04 | 2008-10-29 | 天津大学 | Glucose ferulic amide and process for preparing same |
| CN101219953B (en) * | 2008-01-18 | 2010-06-02 | 北京昂立达技术有限责任公司 | Production and application of palmitoyl ferulic acid ethyl ester |
| CN101836972A (en) * | 2010-06-04 | 2010-09-22 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | Novel purposes of ferulic acid |
| CN102232936A (en) * | 2010-04-29 | 2011-11-09 | 江西中医学院 | Prescription and application of capsule for reducing hyperlipidemia model cholesterol |
| CN102875533A (en) * | 2012-11-06 | 2013-01-16 | 中国药科大学 | Dabigatran derivative, preparation method of dabigatran derivative and anti-thrombus application |
| CN103044404A (en) * | 2013-01-14 | 2013-04-17 | 中国药科大学 | Dabigatran derivatives, and preparation method and application thereof in antithrombosis |
| CN102146040B (en) * | 2010-02-09 | 2014-04-02 | 江西中医药大学 | 2-(4-Chlorophenoxy)-2-methylpropionic acid methoxyphenyl propionate compound and synthesis method thereof |
| CN105884731A (en) * | 2014-11-02 | 2016-08-24 | 江西中医药大学 | Chlorophenoxy isobutyric acid methoxy phenyl acrylate compound and synthesis method thereof |
-
2003
- 2003-04-03 CN CN 03109056 patent/CN1439628A/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100429218C (en) * | 2006-04-04 | 2008-10-29 | 天津大学 | Glucose ferulic amide and process for preparing same |
| WO2008062466A3 (en) * | 2006-10-13 | 2008-09-25 | Reliance Life Sciences Pvt Ltd | Cinnamic acid, vanillic acid and benzofuran derivatives for use in the treatment of inflammation and cancer |
| CN101219953B (en) * | 2008-01-18 | 2010-06-02 | 北京昂立达技术有限责任公司 | Production and application of palmitoyl ferulic acid ethyl ester |
| CN102146040B (en) * | 2010-02-09 | 2014-04-02 | 江西中医药大学 | 2-(4-Chlorophenoxy)-2-methylpropionic acid methoxyphenyl propionate compound and synthesis method thereof |
| CN102232936A (en) * | 2010-04-29 | 2011-11-09 | 江西中医学院 | Prescription and application of capsule for reducing hyperlipidemia model cholesterol |
| CN102232936B (en) * | 2010-04-29 | 2014-06-18 | 江西中医药大学 | Prescription and application of capsule for reducing hyperlipidemia model cholesterol |
| CN101836972A (en) * | 2010-06-04 | 2010-09-22 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | Novel purposes of ferulic acid |
| CN101836972B (en) * | 2010-06-04 | 2012-01-25 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | Novel purposes of ferulic acid |
| CN102875533A (en) * | 2012-11-06 | 2013-01-16 | 中国药科大学 | Dabigatran derivative, preparation method of dabigatran derivative and anti-thrombus application |
| CN102875533B (en) * | 2012-11-06 | 2015-06-17 | 中国药科大学 | Dabigatran derivative, preparation method of dabigatran derivative and anti-thrombus application |
| CN103044404A (en) * | 2013-01-14 | 2013-04-17 | 中国药科大学 | Dabigatran derivatives, and preparation method and application thereof in antithrombosis |
| CN105884731A (en) * | 2014-11-02 | 2016-08-24 | 江西中医药大学 | Chlorophenoxy isobutyric acid methoxy phenyl acrylate compound and synthesis method thereof |
| CN105884731B (en) * | 2014-11-02 | 2018-04-10 | 江西中医药大学 | Chlorine Bezalip Tablets methoxybenzene acrylate compounds and its synthetic method |
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