NO donor type matrine derivative and preparation method and medical application thereof

A technology of matrine and derivatives, applied in the fields of medicinal chemistry and pharmacotherapy, can solve the problems of weak, wide pharmacological effects, limited development and utilization, etc.

Active Publication Date: 2014-04-02
ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
View PDF0 Cites 16 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its pharmacological effects are broad but not strong, which limits its development and utilization to a certain extent. Therefore, it is very necessary to use some concepts and methods of modern drug development to further research and develop matrine.

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
  • NO donor type matrine derivative and preparation method and medical application thereof
  • NO donor type matrine derivative and preparation method and medical application thereof
  • NO donor type matrine derivative and preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0229] Synthesis of N-n-butylmatrine (4)

[0230] Take matrine (4.96g, 0.02moL) in a 250mL round bottom flask, add 10% sodium hydroxide (80mL, 0.2moL), reflux reaction under stirring, TLC detection of reaction progress. After the reaction is complete, adjust the pH to 7-8 with 20% sulfuric acid solution under ice bath. Concentrate under reduced pressure, dissolve the residue by heating with methanol, and filter while hot. The filtrate was concentrated under reduced pressure to 1 / 4 volume, acetone was added, stirred vigorously, a precipitate was precipitated, and filtered by suction to obtain 4.06 g of matrine as a white solid. Take matrine acid (2.66g, 0.01mol) and anhydrous K2CO3 (6.9g, 0.05mol) and dissolve it in 20ml of DMF, condense and reflux under stirring at 60-70°C, when the temperature rises to 60°C and the raw materials are completely dissolved, add 3.5 ml (0.03mol) n-butane bromide, which lasted about 6 hours, TLC detected that the reaction was complete. Suction ...

Embodiment 2

[0239] Referring to the method of Example 1, N-n-butyl matrine and 3,4-diphenylsulfonyl-1,2,5-oxadiazole-2-oxide were prepared.

[0240] Preparation of Aminoethanol Furazan (5)

[0241] Add NaH (142mg, 5.9mmol) and aminoethanol (0.2ml, 3.33mmol) into a 50ml round-bottomed flask, keep away from light, stir in an ice-salt bath, and add furazan dissolved in THF, that is, 3,4-dibenzenesulfonate Acyl-1,2,5-oxadiazole-2-oxide (0.5g, 1.37mmol), keep the reaction on ice. TLC detected that the reaction was complete. Water was added to the reaction solution, and after extraction with EtOAc, the organic layer was washed with saturated NaCl, and TLC detected that the organic layer had a single spot. Anhydrous Na 2 SO 4 After drying, it was concentrated to dryness under reduced pressure and weighed 239 mg. The yield is 62%.

[0242] N-Butyl matrine aminoethanol furazan (I 11 )Synthesis

[0243] Add N-n-butyl matrine (85mg, 0.264mmol), DCC (54.4mg, 0.264mmol) into a 50ml round bott...

Embodiment 3

[0245] Referring to Example 1, benzyl N-benzyl matrine and 1,2-ethylene glycol furazan were synthesized.

[0246] Preparation of N-benzylmatrine succinate (6)

[0247] Add 4.48g (0.01mol) benzyl N-benzyl matrine and 35mlTHF into a 100ml round bottom flask, slowly add 0.68g lithium tetrahydrogen aluminum under ice bath conditions, stir for 2 hours, TLC detection shows that the reaction is complete, stop the reaction , slowly add water dropwise under stirring until no bubbles are produced. Suction filtration, the filtrate was extracted with ethyl acetate (3 x 30ml). The organic layer was washed twice with water, anhydrous Na 2 SO 4 Dry and filter. The filtrate was concentrated to dryness under reduced pressure to obtain 3.04 g of milky white powder, namely N-benzylmatrine. mp: 80.0-80.2°C, yield: 88.9%. ESI-MS: 343[M+H] + ;IR(KBr,cm -1 ):υ:3426(O-H);3030(Ar-H);2932,2818(C-H);1612,1558(C 6 h 6 ); 1 H-NMR (300MHz, CDCl 3 ),δ(ppm):1.47-1.97(m,18H,CH 2 ,CH);2.03(s,1H,CH...

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 field of medical chemistry and pharmacotherapeutics, and particularly relates to an NO donor type matrine derivative and a preparation method thereof and application in pharmacy. The compounds have an anti-tumor effect and can be used for preparing anti-tumor medicines. The invention also relates to a preparation method of the compounds.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to a matrine derivative, a preparation method thereof and an application in pharmacy. The compounds have antitumor effects and can be used for preparing antitumor drugs. The invention also relates to processes for the preparation of such compounds. Background technique [0002] Malignant tumors are one of the most important diseases that endanger human health. The research and development of anti-tumor drugs has become an important field of rapid development in today's medical science. Plant-derived antitumor drugs are diverse in their chemical structures and also in their mechanisms of action. A large number of experimental and clinical studies have proved that natural medicines play an important role in the prevention and rehabilitation of tumors. Finding anti-tumor active ingredients from plants not only has great potential in discovering new drugs, ...

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 Applications(China)
IPC IPC(8): C07D471/16A61K31/4375A61K31/496A61P35/00A61P35/02
CPCC07D471/16
Inventor 何黎琴吴亚先杨琦王效山
Owner ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap