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

Catechin-amantadine conjugate and its preparation method and application

A technology of amantadine and catechin, applied in organic chemistry, antiviral agents, etc., can solve the problems of short half-life, low utilization rate, poor stability, etc., and achieve the effect of novel structure, simple route, and improved bioavailability

Active Publication Date: 2021-07-02
GUIZHOU TEA RES INST
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, catechin also has many defects: low solubility, poor stability, short half-life after entering the body, and extremely low utilization rate in organisms

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
  • Catechin-amantadine conjugate and its preparation method and application
  • Catechin-amantadine conjugate and its preparation method and application
  • Catechin-amantadine conjugate and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Preparation of 5,7,3',4',5'-penta-O-benzyl epigallocatechin (2)

[0025] Epigallocatechin (EGC, 3.06g, 10mmol) was dissolved in DMF (50mL), the temperature was lowered to 0°C, potassium carbonate (10.425g, 75mmol) was added, and benzyl bromide (10.2g, 60mmol ), filled with nitrogen, reacted at room temperature, TLC monitored that the reaction was complete, added 300mL water, dichloromethane 100mL extracted 3 times, anhydrous anhydrous NaSO 4 Dry, filter and concentrate. The concentrate was separated and purified by column chromatography to obtain compound 2 (85%). 1 H NMR (600MHz, CDCl 3 )δ7.45–7.27(m,25H),6.81(s,2H),6.28(s,2H),5.13(s,4H),5.06(s,2H),5.02(s,4H),4.89(s ,1H),4.21(s,1H),3.01(d,J=17.1Hz,1H),2.93(dd,J=17.1,4.5Hz,1H). 13 C NMR (151MHz, CDCl 3 )δ158.78,158.28,155.07,153.00,138.34,137.79,136.96,136.89,133.71,128.58,128.54,128.51,128.47,128.46,128.42,128.14,127.97,127.89,127.87,127.79,127.54,127.50,127.20,127.15,106.14 , 100.96, 94.70, 94.13, 78....

Embodiment 2

[0026] Example 2: Preparation of 3-propargyl-5,7,3',4',5'-penta-O-benzyl epigallocatechin (3)

[0027] Add THF (15mL) and (1.05g, 3mmol) in a 200mL round bottom flask, add NaH (60%, 0.144g, 3.6mmol) in batches, after stirring at room temperature for 2h, add propargyl bromide (3.3mmol) dropwise at room temperature ) in THF (15 mL). After the dropwise addition was completed, the reaction was carried out at 65°C for 48 hours. After cooling down to room temperature, ice water and ethyl acetate (30 mL) were added, the organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with NaHCO 3 Aqueous and NaCl aqueous washes, anhydrous NaSO 4 Dry and concentrate. The concentrate was separated and purified by column chromatography to obtain compound 3 (92%). 1 H NMR (600MHz, Chloroform-d) δ7.45–7.29(m,21H),7.28–7.24(m,4H),6.86(s,2H),6.30–6.24(m,2H),5.13(d,J =1.8Hz,4H),5.07(d,J=4.4Hz,2H),5.03(s,2H),5.00(s,2H),4.9...

Embodiment 3

[0028] Embodiment 3: the synthesis of azidoacetic acid derivatives:

[0029]

[0030] Compound bromoacetic acid (6.8mmol) and NaN 3 (1.326g, 20.4mmol) was added to DMF (15mL), stirred at 60°C for 30h, added water (30mL), adjusted pH=2 with 1M hydrochloric acid, extracted with ether (3*30mL), and the extract was washed with saturated NaHCO 3 (3*20 mL) and water (3*30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give azidoacetic acid.

[0031] Azidoacetic acid, yield 89.2%, 1 H NMR (400MHz, CDCl 3 )δ11.68(s,1H),3.97(s,2H); 13 CNMR (100MHz, CDCl 3 )δ174.5,50.0.ESI-MS: m / z[M+H + ]: 102.1.

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 discloses a catechin-amantadine conjugate and its preparation method and application. The derivative structure: the preparation method is: selective protection of catechin; under alkaline conditions, synthesizing the protected catechin terminal alkyne body; synthesis of amantadine azide intermediate; click reaction between terminal alkyne precursor and azidoadamantane precursor to synthesize catechin-adamantane conjugate; deprotection synthesis of catechin-amantadine under hydrogenation catalyst couples. The synthetic catechin-amantadine conjugate has novel structure, simple synthesis route, no noble metal catalyst, and the synthesized catechin amantadine has good anti-influenza activity.

Description

technical field [0001] The invention relates to the technical fields of chemical synthesis and medicine, and more specifically relates to a catechin-amantadine conjugate and a preparation method and application thereof. Background technique [0002] Tea polyphenols is a general term for polyphenols in tea. Among them, catechin has the most content, accounting for 60% to 80% of tea polyphenols. There are four main components in catechin: epicatechin (EC), epigallocatechin (EGC), epicatechin gallate (ECG), epigallocatechin Ethyl gallate (EGCG). Studies have found that epigallocatechin, a catechin compound in tea, has good anti-avian influenza virus activity in vitro, and can achieve antiviral effect by inhibiting the activity of avian influenza virus reverse transcriptase. However, catechin also has many defects: low solubility, poor stability, short half-life after entering the body, and extremely low utilization rate in organisms. Catechin is used to resist avian influen...

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): C07D405/12A61P31/16
CPCA61P31/16C07D405/12
Inventor 雷志伟杨文李露露陈瑶刘惠芳郭灿
Owner GUIZHOU TEA RES INST
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