Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of isoandrographolide compound and its preparation method and application

A technology of ester compound and andrographis paniculata, applied in the field of isoandrographolide compounds and their preparation, can solve the problems of not being effectively contained, and achieve novel structure, good application prospects, and good antitumor activity

Active Publication Date: 2017-06-06
SOUTH CHINA UNIV OF TECH
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

What is more serious is that this momentum has not been effectively curbed. According to the forecast of the International Agency for Research on Cancer, if no effective measures are taken, the number of cancer cases and deaths in my country will rise to 4 million and 3 million by 2020; will rise to 5 million and 3.5 million people per year

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
  • A kind of isoandrographolide compound and its preparation method and application
  • A kind of isoandrographolide compound and its preparation method and application
  • A kind of isoandrographolide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The present embodiment is isoandrographolide compound 19-(2-(4-(4-aminobenzoyl) benzoate base) acetoxy) isoandrographolide (I 1 ) preparation:

[0043] (1) Add isoandrographolide (2.056g, 5.71mmol) and 100mL of dichloromethane into a 150mL round bottom flask, stir magnetically at room temperature until completely dissolved, then add potassium carbonate (1.025g, 7.42mmol). After stirring magnetically at room temperature for 30 min, bromoacetyl chloride (546 μL, 6.28 mmol) was added, and stirred magnetically at room temperature for 6 h. After the reaction was completed, the reaction solution was diluted with 100 mL of dichloromethane, washed with saturated brine (100 mL×3), dried over anhydrous magnesium sulfate, filtered, and separated by silica gel column chromatography (developing agent V 石油醚 / V 乙酸乙酯 =1 / 1), the product 19-bromoacetyl-isoandrographolide (1.330 g, 50%) was obtained as a white solid. The product identification data is: m.p.121.4°C. 1 H-NMR (CDCl 3 ,4...

Embodiment 2

[0046] The present embodiment is isoandrographolide compound 19-(3-(4-(4-aminobenzoyl) benzoate group) propionyloxy) isoandrographolide (I 2 ) preparation:

[0047] (1) Add isoandrographolide (2.043g, 5.71mmol) and 100mL of dichloromethane into a 150mL round bottom flask, stir magnetically at room temperature until completely dissolved, then add DMAP (1.047g, 7.42mmol). After magnetic stirring at room temperature for 30 min, 3-bromopropionyl chloride (627 μL, 6.28 mmol) was added and magnetic stirring at room temperature for 6 h. After the reaction was completed, the reaction solution was diluted with 100 mL of dichloromethane, washed with saturated brine (100 mL×3), dried over anhydrous magnesium sulfate, filtered, and separated by silica gel column chromatography (developing agent V 石油醚 / V 乙酸乙酯 =1 / 1), the white solid product 19-bromopropionyl-isoandrographolide (1.012 g, 37%) was obtained. The product identification data is: m.p.122.0℃. 1 H-NMR (CDCl 3,400MHz)δ:7.28(1H,...

Embodiment 3

[0050] The present embodiment is isoandrographolide compound 19-(4-(4-(4-aminobenzoyl) benzoate base) butyryloxy) isoandrographolide (I 3 ) preparation:

[0051] (1) The preparation method is the same as in Example 1, reacting isoandrographolide with 4-bromobutyryl chloride, and separating by silica gel column chromatography (developing agent V 石油醚 / V 乙酸乙酯 =1 / 1), the white solid product 19-bromobutyryl-isoandrographolide (1.553 g, 55%) was obtained. The product identification data is: m.p.122.3℃. 1 H-NMR (CDCl 3 ,400MHz)δ:7.28(1H,over signal,H-14),4.81(2H,s,H-15),4.71(1H,t,J=7.3Hz,H-12),4.45(1H,d, J=11.7Hz, H-19a), 4.16(1H, d, J=11.7Hz, H-19b), 3.47(2H, t, J=6.4Hz, H-CO(CH 2 ) 2 C H 2 ),3.30(1H,dd,J=10.9,5.0Hz,H-3),2.55-2.41(3H,m,H-COC H 2 (CH 2 ) 2 ,11a),2.25-1.93(5H,m,H-1a,11a,-COCH 2 C H 2 CH 2 ),1.82-1.49(7H,m,H-1b,2,6,7a,9),1.20-0.95(11H,m,H-5,7b,17,18,20); IR(KBr,cm -1 )ν: 3553,3468,3103,2972,2945,2922,2868,1740,1715,1653,1445,1213,1132,1088,932,840,690,...

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 belongs to the technical field of medicine chemical industry, and discloses an isoandrographolide compound, a preparing method thereof and an application thereof. The structure of the isoandrographolide compound is shown as the formula I (please see the specification), wherein n is an integer equal to 1 to 4, R1 is any one kind of hydroxyl, acetoxyl and bromo-acetoxyl, and R2 is hydrogen or bromo-acetyl. The synthesis method of the isoandrographolide compound includes the steps that isoandrographolide and bromacyl chloride are subjected to an esterification reaction, 19-bromo-acyl-isoandrographolide is obtained, then the 19-bromo-acyl-isoandrographolide and 4-(4-amino-benzoyl)benzoic acid are subjected to an esterification reaction or the 19-bromo-acyl-isoandrographolide and acetic anhydride are continuously subjected to an acylation reaction or the 19-bromo-acyl-isoandrographolide and bromoacetyl bromide are subjected to an esterification reaction, and the isoandrographolide compound is obtained. The preparing method is simple in synthesis route and high in synthesis yield; the obtained product is good in antitumor activity and has good application prospects.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to an isoandrographolide compound and a preparation method and application thereof. Background technique [0002] Malignant tumors are malignant diseases that seriously threaten human life. The World Cancer Report estimates that in 2012, the number of cancer cases in my country was 3.065 million, accounting for about one-fifth of the global incidence; the number of cancer deaths was 2.205 million, accounting for about one-quarter of the global cancer deaths. According to the situation learned by the National Cancer Prevention and Research Office and medical experts in the East, Central and West, and some clinical statistics, due to the aging population and other reasons, the current incidence and mortality of cancer in my country are showing a continuous increase trend. What is more serious is that this momentum has not been effectively curbed. Ac...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/92A61K31/365A61P35/00
CPCC07D307/92
Inventor 李晶张雷杨超
Owner SOUTH CHINA UNIV OF TECH