Tetrahydrofuran diquinoline compound, synthesis method and application thereof

A synthesis method and compound technology, applied in the field of medicine, can solve problems such as no report on synthesis, and achieve the effects of simple and easy-to-control synthesis method, significantly inhibiting activity, and short cycle.

Active Publication Date: 2020-01-14
GUANGXI NORMAL UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many methods for synthesizing quinoline compounds and furan compounds, there is no report on the synthesis of tetrahydrofuro[2,3-b][3',2'-b]diquinoline compounds

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
  • Tetrahydrofuran diquinoline compound, synthesis method and application thereof
  • Tetrahydrofuran diquinoline compound, synthesis method and application thereof
  • Tetrahydrofuran diquinoline compound, synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018]

[0019] Concrete synthesis method: add N-(2-chloromethyl)phenyl-4-methylbenzenesulfonamide (1 is the compound shown in formula (II), 1mmol) and sodium carbonate (1mmol) in 10mL reaction tube, Then furan (2, 0.5mmol) and dichloromethane (2.0mL) were added, and it was stirred and reacted at 25°C for 6h; ), collect and combine the organic phases, filter after drying with anhydrous sodium sulfate, remove the solvent under reduced pressure, and separate the residue by silica gel column chromatography (petroleum ether / ethyl acetate=30:1~1:1, volume ratio), Compound 3 was obtained.

[0020] The obtained compound 3 is characterized as follows:

[0021] 1) White solid, 0.071g, 60% yield; mp: 232-233℃;

[0022] 2) 1 H NMR (400MHz, CDCl 3 ): δ7.62(d, J=7.6Hz, 1H), 7.57(d, J=8.0Hz, 1H), 7.42(d, J=8.0Hz, 2H), 7.30(d, J=8.0Hz, 3H ),7.20-7.14(m,6H),7.09(d,J=7.6Hz,2H),7.01(d,J=6.8Hz,1H),5.95(d,J=7.6Hz,1H),4.21(d ,J=7.6Hz,1H),4.10(d,J=7.6Hz,1H),2.77-2.72(m,2H),2.45(d,J=15.2Hz,...

Embodiment 2

[0029] Example 1 was repeated, except that sodium carbonate was replaced by tripotassium phosphate, dichloromethane was replaced by benzene, the reaction was carried out under ice-bath conditions, and the reaction time was changed to 36 hours. A white solid was finally obtained, 71% yield.

[0030] The resulting white solid was analyzed by H NMR, C NMR, IR, and high-resolution mass spectrometry, and was determined to be the target compound tetrahydrofuran [2,3-b][3',2'-b]biquinoline.

Embodiment 3

[0032] Repeat Example 1, the difference is: replace sodium carbonate with cesium hydroxide, replace dichloromethane with a composition of tetrahydrofuran and ethyl acetate (the volume ratio of tetrahydrofuran and ethyl acetate is 1:1), and change the reaction at 50°C conditions, the reaction time was changed to 10h. Finally a white solid was obtained, 51% yield.

[0033] The resulting white solid was analyzed by H NMR, C NMR, IR, and high-resolution mass spectrometry, and was determined to be the target compound tetrahydrofuran [2,3-b][3',2'-b]biquinoline.

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 tetrahydrofuran diquinoline compound and a synthesis method and an application thereof. The synthesize of the tetrahydrofuran diquinoline compound having the structure represented by the follow formula (I), and the synthesis method mainly comprises the following steps: the compound represented by the following formula (II), furan and alkaline substance are placed in an organic solvent and reacted in the presence of oxygen to obtain a crude product of the target compound. The in vitro test results of the applicant show that the tetrahydrofuran diquinoline compound of the invention shows extremely significant inhibitory activity on various human tumor strains. The compounds of the structure represented by the formula (I) and the formula (II) are as follows.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a tetrahydrofuran biquinoline compound and its synthesis method and application. Background technique [0002] Quinoline and furan are two important classes of heterocyclic compounds, which are the pharmacophore that regulates the biological activity of compounds. Tetrahydrofuro[2,3-b][3',2'-b]biquinoline compounds are a new class of heterocyclic skeletons, which are fusions of two important heterocycles, furan and quinoline. Although there are many methods for synthesizing quinoline compounds and furan compounds, there is no report on the synthesis of tetrahydrofuro[2,3-b][3',2'-b]diquinoline compounds. Therefore, it is very meaningful to study the synthesis method and application of tetrahydrofuro[2,3-b][3',2'-b]biquinoline compounds. Contents of the invention [0003] The technical problem to be solved by the present invention is to provide a tetrahydrofuran biquinoline c...

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): C07D491/147A61K31/4375A61P35/00
CPCA61P35/00C07D491/147
Inventor 莫冬亮雷禄姚懿芸苏桂发
Owner GUANGXI NORMAL UNIV
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