Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Puerarin derivative, preparation method thereof, and application thereof in preventing and treating cardiovascular and cerebrovascular diseases or diabetes mellitus or its complications

A technology of puerarin and drugs, applied in the field of cardiovascular and cerebrovascular and diabetes treatment, can solve problems such as poor water solubility, and achieve the effects of improving solubility, arterial contraction and relaxation, and improving physiological activity

Active Publication Date: 2017-11-03
SHANDONG UNIV
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the problems existing in the prior art, in order to overcome the shortcomings and deficiencies of puerarin's poor water solubility, the present invention uses puerarin as a raw material, firstly by modifying its skeleton, reducing the C ring α, β unsaturated double bonds, and destroying the molecular rigid structure , improve its solubility; secondly, by further reducing the ketone carbonyl to hydroxyl, improve the molecular polarity and water solubility

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Puerarin derivative, preparation method thereof, and application thereof in preventing and treating cardiovascular and cerebrovascular diseases or diabetes mellitus or its complications
  • Puerarin derivative, preparation method thereof, and application thereof in preventing and treating cardiovascular and cerebrovascular diseases or diabetes mellitus or its complications
  • Puerarin derivative, preparation method thereof, and application thereof in preventing and treating cardiovascular and cerebrovascular diseases or diabetes mellitus or its complications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment one: the structure of the compound of the present invention is as follows:

[0032]

[0033] The pharmaceutically acceptable salts of the above-mentioned compounds are the salts formed between the compound and inorganic bases, such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, calcium chloride, calcium acetate or magnesium chloride, or with organic bases, such as amino Salts of butanetriol, aminoethanol, lysine or arginine, etc.

Embodiment 2

[0034] Embodiment two: the preparation of compound 1 and 2

[0035]

[0036] Weigh the compound puerarin (III) and place it in a dry round bottom flask, add ethyl acetate to dissolve it, then add 10% palladium carbon, stir and react at room temperature for 6 hours, TLC monitors the reaction process, after the reaction, filter the palladium carbon , the solvent was evaporated, and the obtained product was passed through a Flash reversed-phase column, and the mobile phase was methanol / water gradient elution, and finally the solvent was evaporated under reduced pressure to obtain compounds 1 and 2 as white solids.

[0037] Compound 1: MS m / z: 419 (M+1); 1 H NMR (400MHz, MeOD) δ7.75(d, J=8.8Hz, 1H), 7.08(d, J=8.6Hz, 2H), 6.75(d, J=8.5Hz, 2H), 6.54(d, J =8.8Hz,1H),4.93–4.88(m,2H),4.63–4.52(m,2H),4.04(s,1H),3.87(dd,J=11.9,1.9Hz,1H),3.73(dd, J=11.9,4.9Hz,1H),3.50–3.36(m,3H).

[0038] Compound 2: MS m / z: 419 (M+1); 1 H NMR (400MHz, MeOD) δ7.75(d, J=8.8Hz, 1H), 7.12(d, J=8.5Hz, 2H...

Embodiment 3

[0039] Embodiment three: the preparation of compound 3 and 4

[0040]

[0041] Weigh the compound dehydrated puerarin (V) and place it in a dry round bottom flask, add ethyl acetate to dissolve it, then add 10% palladium carbon, stir and react at room temperature for 6 hours, TLC monitors the reaction process, after the reaction, filter out the palladium carbon, the solvent was distilled off, and the obtained product was passed through a Flash reverse-phase column, and the mobile phase was methanol / water gradient elution, and finally the solvent was distilled off under reduced pressure to obtain compounds 3 and 4 as white solids.

[0042] Compound 3: MS m / z: 401 (M+1); 1 H NMR (600MHz, CD 3 OD) δ7.92(d, J=8.6Hz, 1H), 7.08(d, J=8.6Hz, 2H), 6.77(d, J=8.6Hz, 2H), 6.68(d, J=8.6Hz, 1H ),5.18(d,J=3.3Hz,1H),4.70–4.55(m,3H),4.00-3.97(m,2H),3.84(dd,J=12.1,2.5Hz,1H),3.64(dd, J=12.1,5.7Hz,1H),3.60(t,J=9.4Hz,1H),3.35(ddd,J=9.3,5.7,2.3Hz,1H).

[0043] Compound 4: MS m / z: 401 (M+1); ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a puerarin derivative, a preparation method thereof, and application thereof in preventing and treating cardiovascular and cerebrovascular diseases or diabetes mellitus or its complications. The invention relates to a puerarin derivative or its pharmaceutically acceptable salt show as formula (I) or formula (II) shown in the description, wherein a symbol shown in the description may represent a single bond or a double bond, R1 represents oxygen atom, hydrogen atom, hydroxy, alkoxy and halogen atom, each of R2 and R3 represents hydrogen atom, hydroxy, hydroxymethyl, halogen atom, -O(O)CR4, -OSOR4, -OSO2R4, and -O(O)PO2R4R5; in addition, the invention also relates to a pharmaceutically acceptable salt of the puerarin derivative. The invention also relates to application of the puerarin derivative and its salt medical composition in preventing and treating cardiovascular and cerebrovascular diseases, diabetes mellitus and their complications, and the puerarin derivative and its salt medical composition may act as main ingredients to prepare corresponding oral preparations, injections and the like; the invention covers joint treatment methods of other drugs for cardiovascular and cerebrovascular diseases.

Description

technical field [0001] The present invention relates to the field of cardiovascular and cerebrovascular and diabetes treatment and the field of compound preparation. Specifically, the present invention relates to the structure and preparation method of new puerarin derivatives and the use of such derivatives in the treatment and prevention of cardiovascular and cerebrovascular diseases or diabetes and their Uses in Complications. Background technique [0002] Puerarin is a flavonoid compound distributed in the roots of pueraria mirifica and kudzu vine, which is one of the main active ingredients of traditional Chinese medicine pueraria. Studies have shown that puerarin is a kind of β-receptor blocker and calcium ion antagonist, which has pharmacological effects such as dilating coronary arteries, lowering blood pressure, antiarrhythmia, lowering blood sugar, lowering blood fat, relaxing smooth muscle, inhibiting platelet aggregation and anti-oxidation Clinically, it is main...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D407/04C07D493/14A61K31/352A61P9/10A61P9/12A61P9/04A61P3/10
CPCC07D407/04C07D493/14
Inventor 娄红祥孙斌崔昌义
Owner SHANDONG UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com