Pentacyclic triterpenoid compound, derivatives of pentacyclic triterpenoid compound and applications

A technology for pentacyclic triterpenoids and compounds, which is applied in the field of chemical pharmacy, can solve the problems of large molecular weight, difficult to prepare on a large scale, and no treatment method has been found, and achieves the effects of improving cognition and high activity

Active Publication Date: 2018-11-20
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, NGF is a protein composed of more than 100 amino acids; due to reasons such as large molecular weight and strong polarity, it cannot pass through the blood-brain barrier, and it is dif

Method used

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  • Pentacyclic triterpenoid compound, derivatives of pentacyclic triterpenoid compound and applications
  • Pentacyclic triterpenoid compound, derivatives of pentacyclic triterpenoid compound and applications
  • Pentacyclic triterpenoid compound, derivatives of pentacyclic triterpenoid compound and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Compound Ⅰ-1: (3S,4R)-23,28-Dihydroxyolean-12-en-3-yl(2E)-3-(3,4-dihydroxyphenyl)acrylate

[0044] Caffeic acid (A) (408mg, 1mmol), DCC (413mg, 2mmol) and DMAP (122mg, 1.0mmol) protected by phenolic hydroxyl group O-TBS were dissolved in 10mL of anhydrous dichloromethane, cooled to 0°C, and two 3β,23,28-Triol olean-12-ene (B) (34.3 mg, 0.05 mmol) protected by O-TBS with a primary hydroxyl group, and the reaction system was stirred overnight at room temperature. After purification, 30 mg of colorless solid C was obtained, yield: 56%. The compound structure is shown below:

[0045]

[0046] Compound C (21.5 mg, 0.02 mmol) was dissolved in 5 mL of methanol, and camphorsulfonic acid (23 mg, 0.1 mmol) was added. The reaction system was stirred at room temperature for 4 hours. Quenched with water, extracted with ethyl acetate, washed the organic phase with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation to obtain a ...

Embodiment 2

[0051] Compound Ⅰ-2: (3S,4R)-23,28-Dihydroxyolean-12-en-3-yl(2E)-3-phenylacrylate;

[0052] The synthesis method is the same as compound Ⅰ-1, and the reaction materials are: cinnamic acid (1 mmol), DCC (2 mmol), DMAP (1.0 mmol) and compound B (0.05 mmol). 0.02 mmol of the obtained product was dissolved in 5 mL of methanol, and 0.05 mmol of camphorsulfonic acid was added.

[0053] 1 H NMR (500MHz, CDCl 3 ):7.65(d,J=16.0Hz,1H),7.62(m,2H),7.43(m,3H),6.53(d,J=16.0Hz,1H),5.23(t,J=3.5Hz,1H ),5.03(dd,J=11.5.0,6.0Hz,1H),3.56(d,J=11.0Hz,1H),3.39(d,J=12.0Hz,1H),3.19(d,J=11.0Hz ,1H),3.14(d,J=12.0Hz,1H),1.25(s,3H),1.09(s,3H),1.04(s,3H),0.92(s,6H),0.87(s,3H) . 13 C NMR (125MHz, CDCl 3 )167.8,145.8,141.8,134.5,130.3,128.9,128.1,123.4,117.9,75.8,69.8,64.7,49.1,47.9,47.8,43.8,43.4,43.0,41.2,39.2,38.1,37.331.3,38,3,3 ,32.3,31.8,26.6,26.6,24.6,24.1,23.5,22.9,18.8,17.3,16.5,13.9.HRMS:m / z[M+Na] + calcd for C 39 h 56 o 4 Na:611.4071,found:611.4063.

[0054] The structural formula of th...

Embodiment 3

[0057] Compound Ⅰ-3: (3S,4R)-23,28-Dihydroxyolean-12-en-3-yl(2E)-3-(3-hydroxyphenyl)acrylate;

[0058] The synthesis method is the same as compound Ⅰ-1, and the reaction materials are: 3-hydroxycinnamic acid (1 mmol) protected by phenolic hydroxyl O-TBS, DCC (2 mmol), DMAP (1.0 mmol) and compound B (0.05 mmol). 0.02 mmol of the obtained product was dissolved in 5 mL of methanol, and 0.07 mmol of camphorsulfonic acid was added.

[0059] 1 H NMR (500MHz, CDCl 3 ):7.63(d,J=16.0Hz,1H),7.23(t,J=8.0Hz,1H),7.05(d,J=8.0Hz,1H),7.00(t,J=2.5Hz,1H), 6.85(dd, J=8.0,2.5Hz,1H),6.47(d,J=16.0Hz,1H),5.21(t,J=3.5Hz,1H),5.02(dd,J=11.0,6.0Hz,1H ),3.54(d,J=11.0Hz,1H),3.38(d,J=11.5Hz,1H),3.18(d,J=11.0Hz,1H),3.11(d,J=11.5Hz,1H), 1.13(s,3H),1.02(s,3H),0.99(s,3H),0.88(s,3H),0.87(s,3H),0.86(s,3H). 13 C NMR (125MHz, CDCl 3 )168.2,159.5,146.3,145.8,136.1,131.5,123.4,121.9,119.2,118.1,115.5,75.1,69.9,65.2,49.1,47.3,46.9,43.8,43.1,42.5,41.6,33.2,378.3,38.3 ,33.3,33.1,32.4,31.8,26.4,26.4,24.6,24.1,24....

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Abstract

The invention provides a pentacyclic triterpenoid compound and derivatives of the pentacyclic triterpenoid compound. The pentacyclic triterpenoid compound and the derivatives of the pentacyclic triterpenoid compound have the significant pseudo nerve growth factor activity and are small-molecular compounds which can pass the blood brain barrier. Thus, through addition of the pentacyclic triterpenoid compound and the derivatives of the pentacyclic triterpenoid compound to pharmaceutically acceptable carriers, drugs for preventing and treating neurodegenerative diseases such as senile dementia (particularly the Alzheimer's disease) and the like can be prepared. Or the pentacyclic triterpenoid compound and the derivatives of the pentacyclic triterpenoid compound are used as active components,food acceptable carriers are added, and food for preventing and treating the neurodegenerative diseases such as the senile dementia and the like can be prepared. The pentacyclic triterpenoid compoundand the derivatives of the pentacyclic triterpenoid compound can also be applied to preparation of food and drugs for preventing and treating the neurodegenerative diseases or improving the cognitiveability and the learning and memory ability. The general structural formula is shown in the Formula I shown in the description.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy and relates to pentacyclic triterpenoid compounds, in particular to a pentacyclic triterpenoid compound and its derivatives and applications. Background technique [0002] With the rapid development of society and the great improvement of human living standards and medical and health care, human life expectancy is prolonged, and the aging process is gradually accelerating. The aging of the population is already a global problem. [0003] According to the main data of the sixth national census released by the National Bureau of Statistics, as of November 1, 2010, the total population of my country was 1.34 billion. Among them, the population over the age of 60 reached 178 million, accounting for 13.26% of the total population of the country, an increase of 2.93% over 2000; the population over the age of 65 reached 119 million, accounting for 8.87% of the total population of the country, an increase...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61K31/58A61P25/28A23L33/10
CPCA23L33/10A23V2002/00A61P25/28C07J63/008A23V2200/322
Inventor 戚建华边凌林程丽红
Owner ZHEJIANG UNIV
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