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

Š�-elemen-5-azacycle ramification and its synthetic method

A five-membered nitrogen heterocycle and elemene technology, applied in the direction of organic chemistry, can solve the problems of poor water solubility, and achieve the effects of mild reaction conditions, easy control of reaction conditions, and simple synthesis methods

Inactive Publication Date: 2003-12-24
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
View PDF0 Cites 17 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Elemene has been used clinically as a traditional Chinese medicine, but its water solubility is extremely poor, and how to further improve its antitumor activity remains to be studied

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
  • Š�-elemen-5-azacycle ramification and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Step 1, β-elemene reacts with hypochlorite in acetic acid to prepare the halogenated product intermediate

[0026] In a 100mo round bottom bottle equipped with an electromagnetic stirrer, add 10.2g β-elemene and 10ml glacial acetic acid, and control the reaction temperature at about 0-5°C. Add 40ml of sodium hypochlorite (containing 8.6% available chlorine) dropwise from a constant pressure dropping funnel under vigorous stirring, and pay attention to maintaining the temperature of the reaction system not exceeding 5°C, and complete the addition within 4 hours. Stirring was continued at this temperature for 1 hour, then the reaction mixture was poured into a separatory funnel, extracted 3 times with petroleum ether (3×60 ml), and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated to obtain a yellow oil, which was subjected to silica gel column chromatography to obtain 6.8 g of β-elemene chloride for the reaction ...

Embodiment 2

[0030] Step 1. FeCl 3 Treatment of other transition metals

[0031] Dissolve 5g of ferric chloride in 10mL of acetone, then add 20g of silica gel, remove acetone under reduced pressure on a rotary evaporator, then place the silica gel in an oven, dry at 120°C for 3-4 hours, and cool Store in a desiccator for later use. NiCl was prepared in the same way 2 , CoCl 2 catalyst. IrCl 3 The preparation method is to IrCl 3 Dissolve in 20ml of water, then distill off most of the water under reduced pressure, place the obtained powder in an oven, dry at 140°C for 4-5 hours, cool naturally and place in a desiccator for later use.

[0032] Step 2, β-elemene uses hypochlorite to prepare halogenated intermediates under the catalyzed reaction of transition metal chlorides

[0033] In a 100ml round bottom bottle equipped with an electromagnetic stirrer, add 10.2g β-elemene, 50ml n-hexane, FeCl 3 50%moL), cooled to below 0°C, and 40ml of sodium hypochlorite (containing 8.6% of availabl...

Embodiment 3

[0037] Step 1. FeCl 3 The processing such as transition metal is the same as embodiment 2.

[0038] Step 2, β-elemene uses NBS to prepare β-elemene bromide intermediate under transition metal chloride catalyzed reaction

[0039] In a 100mL round bottom bottle equipped with an electromagnetic stirrer, add 10.2g β-elemene, 30mL ether, 10% moL of cobalt dichloride, cool to below 0°C, add 10gNBS in batches under vigorous stirring, and react After 4 hours, the reaction solution was filtered, washed with n-hexane, and then the organic phase was concentrated and subjected to fast silica gel column chromatography, using petroleum ether as the eluent to remove inorganic salts and succinimide generated by the reaction to obtain unreacted β-elemene and β-elemene bromide, this mixture was used directly in the reaction of step 3. It is also possible to obtain a relatively pure β-elemene bromide for the reaction of step 3 by further column chromatography.

[0040] Step 3, preparation of ...

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

A beta-elemene five-element azacyclic derivative is disclosed, which is prepared through reaction of beta-elmene on hypochlorite or NBS to obtain intermediate, and reacting on 1,3,4-oxadiazole or 1,2,4-triazole thiol in DMF or DMSO solvent to obtain beta-elemene, 1,3,4-oxadiazole (or 1,2,4-triazole) derivative.

Description

technical field [0001] The invention relates to an organic compound β-elemene and a series of β-elemene five-membered nitrogen heterocyclic derivatives, and provides a method for synthesizing the series of derivatives. Background technique [0002] In the study of anticancer drugs, it has been reported that nitrogen-containing alkaloids and terpene compounds have anticancer effects, such as the newly developed sesquiterpene compound elemene in my country is one of them. β-elemene is a kind of traditional Chinese medicine anticancer drug originated from my country, and its molecular formula is C 15 h 24 , the structural formula is as (1) [0003] Elemene has been used clinically as a traditional Chinese medicine, but its water solubility is extremely poor, and how to further improve its antitumor activity remains to be studied. Contents of the invention [0004] One of the objectives of the present invention is to provide nitrogen-containing five-membered heterocyclic ...

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): C07D249/12
Inventor 褚长虎梁鑫淼肖红斌胡皆汉
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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