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

Shikimic acid compound and preparation method and application thereof

A compound, shikiki technology, applied in a class of shikimic acid compounds and its preparation and use, can solve problems such as inability to pass through the blood-brain barrier, limited application, and difficult absorption after oral administration

Inactive Publication Date: 2010-06-09
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
View PDF0 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Shikimic acid itself has disadvantages such as high polarity, difficulty in oral absorption, and inability to pass through the blood-brain barrier, which limit its application as a drug

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
  • Shikimic acid compound and preparation method and application thereof
  • Shikimic acid compound and preparation method and application thereof
  • Shikimic acid compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1 (compound c1):

[0028]

[0029] Add 500 mg of triacetylshikimic acid a (Bi Yi et al., Journal of China Pharmaceutical University, 2007, 38(2), 108-111). Dissolve in 5 mL of thionyl chloride, reflux for 2 hours, and spin dry under reduced pressure to obtain 525 mg of crude triacetylshikimoyl chloride (compound b), which can be directly used in the next reaction.

[0030] Add 70mg Pd(PPh 3 ) 4 , 665mgK 3 PO 4 ·3H 2 O, 183mg PhB(OH) 2 (phenylboronic acid) and 5mL anhydrous toluene, N 2 Reaction at 80°C for 8h under protection. After the reaction liquid was cooled, it was poured into water, extracted three times with ethyl acetate, the organic phases were combined and dried, spin-dried, and separated by petroleum ether: ethyl acetate = 4:1 silica gel column chromatography to obtain 390 mg of the target compound. 1 HNMR: 87.69-7.66 (m, 2H), 7.58-7.52 (m, 1H), 7.47-7.42 (m, 2H), 6.30-6.28 (m, 1H), 5.82-5.79 (m, 1H), 5.42-5.35 (m, 1H), 5.32-5.28 (m, 1...

Embodiment 2

[0031] Embodiment 2 (compound c2)

[0032]

[0033] The preparation process is the same as in Example 1, except that phenylboronic acid is replaced by p-tolylboronic acid. 1 HNMR: δ7.62-7.59(d, 2H, J=7.8), 7.26-7.23(d, 2H, J=7.8), 6.27-6.26(t, 1H, J=1.8), 5.80(s, 1H), 5.40-5.35 (m, 1H), 5.32-5.28 (m, 1H), 3.15-3.07 (dd, 1H, J=18.6, 4.8), 2.56-2.48 (dd, 1H, J=18.6, 4.8), 2.40 ( s, 3H), 2.08 (s, 3H), 2.06 (s, 6H). Yield: 72%.

Embodiment 3

[0034] Embodiment 3 (compound c3)

[0035]

[0036] The preparation process is the same as in Example 1, except that phenylboronic acid is replaced by p-methoxyphenylboronic acid. 1 HNMR: δ7.73-7.70(d, 2H, J=9), 6.94-6.90(d, 2H, J=9), 6.22-6.19(m, 1H), 5.80-5.77(t, 1H, J=3.9 ), 5.41-5.34(m, 1H), 5.30-5.26(m, 1H), 3.84(s, 3H), 3.13-3.05(dd, 1H, J=18.6, 5.7), 2.54-2.46(dd, 1H, J = 18.6, 6.3), 2.07 (s, 3H), 2.06 (s, 3H), 2.05 (s, 3H). Yield: 60%.

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 a shikimic acid compound and a preparation method and application thereof. Specifically, the invention relates to the shikimic acid compound having the following structural general formula, wherein the definition of each substituting group is as shown in the specification. The shikimic acid compound can be used for preparing anti-tumor and / or anti-tuberculosis medicaments.

Description

technical field [0001] The present invention relates to a novel shikimic acid compound and its preparation method and use. Background technique [0002] Shikimic acid: The chemical name is [3R-(3α, 4α, β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid, which is a variety of Chinese herbal medicine Magnoliaceae star anise Medicinal ingredients contained in the fruit of the plant. In recent years, it has received widespread attention for its antibacterial and antitumor effects and its effects on the cardiovascular system (Qiu Mi et al., A Review of Shikimic Acid, Guangxi Forestry Science, 2009, 38, (1), 45-47). [0003] Shikimic acid has a core structure of carbasugars - a multifunctional cyclohexene structure. It is currently known that many natural products contain this core structure, such as cyathiformines A-D and Pericosines A-E and other series of compounds. Compounds with this characteristic structure often have multiple biological activities. For example, Pericos...

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): C07D333/56C07D333/22C07D317/54C07D307/80C07C69/18C07C67/293C07C205/45C07C201/12C07C49/83C07C49/84C07C45/61A61K31/215A61K31/36A61K31/381A61K31/343A61K31/121A61P35/00A61P31/06
Inventor 江敏贺茜杨春皓谢毓元
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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