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

Phenanthroquinolizidine alkaloid derivatives and salts thereof, and preparation, anti-plant virus activity and anti-cancer activity of phenanthroquinolizidine alkaloid derivatives and salts thereof

A technology of alkaloid derivatives, phenanthroquinol, which is applied in the field of phenanthroquinolizidine alkaloid derivatives and their salts, and can solve the problem of unrepeatable, photothermal instability, and phenanthroquinolizidine derivatives. Single structure and other problems, to achieve good anti-cancer activity, excellent anti-plant virus activity

Active Publication Date: 2014-01-15
NANKAI UNIV
View PDF8 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] WO03070166 discloses the preparation method of phenanthroquinolizidine derivatives and their application in medicine, but the route is long and the conditions are harsh and difficult to repeat, and it is reported that the structure of phenanthrenequinolizidine derivatives is single, and the activity is mainly Concentrate on two tumor cell lines, KB and HepG2; WO2011049704 discloses the preparation method of phenanthroquinolizidine derivatives and their application in medicine. (R)-Cryptopleurine and its E-ring nitrogen-oxygen-containing derivatives and their anticancer activity; ZL200610129555.1 discloses the application of phenanthroquinolizidine derivatives and their salts in pesticides, because the compound reported in the patent It has the disadvantages of poor water solubility and photothermal instability, and only in vitro activity tests have been carried out

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
  • Phenanthroquinolizidine alkaloid derivatives and salts thereof, and preparation, anti-plant virus activity and anti-cancer activity of phenanthroquinolizidine alkaloid derivatives and salts thereof
  • Phenanthroquinolizidine alkaloid derivatives and salts thereof, and preparation, anti-plant virus activity and anti-cancer activity of phenanthroquinolizidine alkaloid derivatives and salts thereof
  • Phenanthroquinolizidine alkaloid derivatives and salts thereof, and preparation, anti-plant virus activity and anti-cancer activity of phenanthroquinolizidine alkaloid derivatives and salts thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: Synthesis of phenanthroquinolizidine alkaloid derivatives I-a-1~I-a-13

[0040] 2,3-Dimethoxy-6-benzyloxy-phenanthrene-[9,10-b]-quinolizidine (I-a-8) and 6-hydroxy-2,3-dimethoxy-phenanthrene -[9,10-b]-quinolizidine (I-a-9) synthesis:

[0041]

[0042]Synthesis of 2-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)methyl acrylate Add 19.6g (0.1mol) 3,4-dimethyl in sequence to a 250mL four-necked reaction flask Oxyphenylacetic acid, 12.2g (0.1mol) 4-methoxybenzaldehyde, 40mL acetic anhydride and 20mL triethylamine were stirred and heated for 20h. The mixture was cooled to room temperature, 60 mL of water was added thereto, reacted for 8 h, filtered, and washed with methanol to obtain a yellow solid, 22.1 g in total, and the above yellow solid, 600 mL of methanol, and 4 g of concentrated sulfuric acid were added to a 1 L four-neck flask, and heated Reaction 12h. The reaction solution was desolvated to obtain a brown solid, which was recrystallized with methanol...

Embodiment 2

[0082] Embodiment 2: Synthesis of phenanthroquinolizidine alkaloid derivatives I-b-1~I-b-7 and I-c-1

[0083] 2,3,6,7-Tetrabenzyloxycarbonyloxy-phenanthrene-[9,10-b]-quinolizidine (I-b-1) and 2,3,6,7-tetrahydroxy-phenanthrene- Preparation of [9,10-b]-quinolizidine (I-c-1)

[0084]

[0085] Synthesis of 2,3,6,7-tetrabenzyloxycarbonyloxy-phenanthrene-[9,10-b]-quinolizidine (I-b-1) Add 0.4g (1mmol) to a 250mL one-necked bottle 2,3,6,7-Tetramethoxy-phenanthrene-[9,10-b]-quinolizidine (I-a-7), 80mL dichloromethane, install constant pressure dropping funnel and drying tube, in Add 20mL of dichloromethane and 3mL of boron tribromide into the constant pressure dropping funnel, put the reaction bottle into a low-temperature bath, stir the reaction, and add the dichloromethane solution of boron tribromide dropwise. After the dropwise addition, react for 36h. Add methanol, spin out the reaction solution, add 60mL of water and 60mL of tetrahydrofuran to dissolve the residue, pour it...

Embodiment 3

[0101] Example 3: 2,3,6,7-tetramethoxy-phenanthrene-[9,10-b]-quinolizidine-9-formic acid ethyl ester (I-d-1) and 2,3,6, Preparation of 7-tetramethoxy-phenanthrene-[9,10-b]-quinolizidine-9-methanol (I-d-2)

[0102]

[0103] Synthesis of ethyl 2,3,6,7-tetramethoxy-phenanthrene-[9,10-b]-quinolizidine-9-carboxylate (I-d-1)

[0104] In a 100mL four-neck flask, add 0.8g (2mmol) 2-(2,3,6,7-tetramethoxy-9-phenanthrenylmethyl)-piperidine, 60mL acetonitrile, pass through argon protection, add 2.6 mL50% ethyl glyoxylate solution in toluene, add 0.1mL glacial acetic acid. The reaction was stirred at room temperature for 24h. Add saturated sodium bicarbonate solution for treatment, extract with dichloromethane, wash twice with saturated sodium bicarbonate, then wash once with saturated brine, add anhydrous sodium sulfate to dry, filter and precipitate to obtain a yellow solid 0.9g, yield 83.3%, melting point 167-169°C; 1 H NMR (400MHz, CDCl 3 )δ1.25(t, J=7.2Hz, 3H), 1.41-1.54(m, 2H...

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

Provided are phenanthroindolizidine alkaloid derivates and salt thereof as well as preparation, a plant-virus resisting activity, and an anti-cancer activity of phenanthroindolizidine alkaloid derivates and salt thereof. The derivates and the salt thereof have a good plant-virus resisting activity, which is capable of well restraining a tobacco mosaic virus (TMV), and meanwhile, have a good anti-cancer activity, which is capable of well restraining the human lung adenocarcinoma A-549 and the human leukemia HL-60.

Description

technical field [0001] The present invention relates to phenanthroquinolizidine alkaloid derivatives and their salts, their preparation, anti-plant virus and anti-cancer applications. Background technique [0002] Phenanthrenequinolizidine alkaloids mainly exist in natural plants such as Lauraceae, Vitaceae and Urticaceae. Since the first phenanthroquinolizidine alkaloid, Cryptopleurine, was isolated and reported in 1948, so far there are only five such alkaloids: (14aR)-Cryptopleurine, Cryptopleuridine, (14aR)-Boehmeriasin A, Boehmeriasin B and (14aR, 15R)-15-Hydroxycryptopleurine were isolated and found. Although the content of this kind of alkaloids is very small in nature, their good biological activities still attract the attention of chemists and pharmacologists. [0003] [0004] WO03070166 discloses the preparation method of phenanthroquinolizidine derivatives and their application in medicine, but the route is long and the conditions are harsh and difficult to ...

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): C07D491/147C07D471/04A01P1/00A61P35/00A61P35/02
CPCC07D455/03C07D491/147A61P1/00A61P3/00A61P35/00A61P35/02C07D471/04C07D498/14
Inventor 汪清民王兹稳冯安政王力钟刘玉秀崔明波
Owner NANKAI UNIV
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