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

Tanshensu methyl pivalate derivative and preparation method thereof

A technology for methyl pivalate and chloromethyl pivalate, applied in the field of danshensu methyl pivalate derivatives and preparation thereof, can solve problems such as low bioavailability of danshensu, and achieve improved bioavailability , the effect of high reaction efficiency and less impurities

Pending Publication Date: 2022-04-26
广东医科大学附属第二医院
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the technical problem of low bioavailability of danshensu, the invention provides a danshensu methyl pivalate derivative

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
  • Tanshensu methyl pivalate derivative and preparation method thereof
  • Tanshensu methyl pivalate derivative and preparation method thereof
  • Tanshensu methyl pivalate derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation of embodiment 1 Danshensu methyl pivalate derivatives

[0031] Weigh 110mg of danshensu sodium and dissolve it in 5mL of DMF, stir to dissolve. 214 μL of chloromethyl pivalate (3 eq) and 34 mg of imidazole (1 eq) were added to the reaction. N 2 Under the conditions, react at 60° C. for 12 h, and detect the reaction by TLC. It was extracted three times with saturated brine / ethyl acetate system, and the organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography to obtain 87 mg of danshensu methyl pivalate derivative with a yield of 56%.

[0032] The NMR data of the prepared Danshensu-methyl pivalate derivatives are as follows:

[0033] 1 H NMR (400MHz, CDCl 3 )δ6.75–6.67(m,2H),6.58(d,J=8.0Hz,1H),5.88–5.82(m,1H),5.75(d,J=5.4Hz,1H),4.45–4.37(m ,1H),2.98(dd,J=14.1,4.2Hz,1H),2.81(dd,J=14.1,6.7Hz,1H),1.22(s,9H).

[0034] 13 C NMR (101MHz, CDCl 3 )δ177.62, 172.93, 143.59, 1...

experiment example

[0035] Experimental example Drug bioavailability experiment

[0036] 18 SD rats were randomly divided into the experimental group of danshensu pivalate methyl ester derivatives, the danshensu control group and the danshensu palmitate control group, with 6 rats in each group; the mice in each group were fed with food after 12 hours of fasting before the experiment. Stomach administration. Blood was collected from the canthus at 15, 30 minutes and 1, 2, 4, 6, 8, 12, 16, 20, and 24 hours after intragastric administration, and then put into a heparin-treated centrifuge tube, centrifuged and drawn In the upper layer of plasma, LPLC-MS method was used to measure the content of Danshensu in the plasma, and the blood concentration of Danshensu was calculated, and the blood concentration-time curve of Danshensu was made according to the blood concentration, and then the AUC was calculated by the trapezoidal method; The larger the value, the higher the bioavailability of the drug; the ...

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 relates to the technical field of medicinal chemistry, and particularly discloses a tanshinol methyl pivalate derivative. The tanshinol methyl pivalate derivative has a structure as shown in a formula I which is described in the specification. The preparation method of the tanshinol methyl pivalate derivative specifically comprises the following steps: dissolving sodium tanshinol in an organic solvent, then adding chloromethyl pivalate and an acid-binding agent, reacting at 40-60 DEG C under the protection of inert gas, and obtaining the tanshinol methyl pivalate derivative after the reaction is finished. Researches show that the tanshinol methyl pivalate derivative prepared by modifying tanshinol with chloromethyl pivalate can greatly improve the bioavailability of tanshinol.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a danshensu methyl pivalate derivative and a preparation method thereof. Background technique [0002] Danshensu is a water-soluble component isolated from Salvia miltiorrhiza, a plant of Labiatae, and it is one of the main medicinal components in the water-soluble components of Salvia miltiorrhiza. Clinically, Danshensu is widely used in the treatment of cardiovascular diseases, anticoagulation, and improvement of microcirculation; in addition, pharmacological experiments show that it also has anti-inflammatory, anti-tumor, anti-cerebral thrombosis, and liver protection effects. [0003] However, Danshensu has the problem of low bioavailability in the specific application process, resulting in greatly reduced efficacy. In order to improve the bioavailability of Danshensu, the prior art (Guo Xuejiao. Synthesis, Characterization and Oral Bioavailability of Danshensu L...

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): C07C69/732C07C67/62C07C67/11
CPCC07C67/11C07C67/62C07C69/732C07B2200/07
Inventor 巫鑫廖红波崔燎缪辉来陈图刚陈灿邢星星张志鹏仪汶鑫林冬玲
Owner 广东医科大学附属第二医院
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