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

Compound and preparation method and application thereof

A compound and reaction technology, applied in the field of fluorescent probes, can solve the problems of slow response speed of G-quadruplex DNA, affect the application value, and poor photostability, and achieve strong photostability, low biological toxicity, and membrane permeability good sex effect

Active Publication Date: 2018-09-21
GUANGDONG UNIV OF TECH
View PDF5 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, a variety of fluorescent probes for G-quadruplex DNA have been found, but few fluorescent probes that only recognize a specific G-quadruplex DNA have been found, and G-quadruplex DNA fluorescent probes Needles have some defects in practical imaging applications, such as slow response to G-quadruplex DNA, high phototoxicity, and poor photostability, which affect their application value.

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
  • Compound and preparation method and application thereof
  • Compound and preparation method and application thereof
  • Compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0046] According to the present invention, the present invention also provides a preparation method of the compound, comprising:

[0047] The compound of formula (II) structure is reacted with the compound of formula (III) structure, obtains the compound of formula (I) structure,

[0048]

[0049] where, the R 1 from C 1-6 Alkylamino, pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or pyroxolinyl.

[0050] According to the present invention, the present invention will react the compound of formula (II) structure with the compound of formula (III) structure, obtain the compound of formula (I) structure, wherein, the present invention does not have special requirement to the condition of reaction, the skilled in the art Personnel can select suitable reaction conditions according to common knowledge in this field, wherein, the temperature of described reaction is preferably 130~150 ℃, more preferably 135~145 ℃; The time of described reaction is preferably 3~4 hours; The ...

Embodiment 1

[0069] Embodiment 1: the synthesis of compound 1a

[0070] Weigh 0.2g (1.130mmol) of 4-chlorodimethylquinoline into a 25ml round-bottomed flask, add about 1.2g of methyl iodide and 5.0ml of sulfolane, and heat the mixture to 60°C for 6 hours of reaction Afterwards, cool, shake after adding ethyl acetate, suction filter, wash the solid with ethyl acetate, weigh after vacuum drying, thin-layer chromatography preliminary shows that there is no by-product, obtains 1.82g pure product 1a, chemical structural formula is as follows, yield was 88.6%.

[0071]

[0072] Utilize nuclear magnetic resonance to analyze the compound 1a obtained in embodiment 1, obtain its proton nuclear magnetic resonance spectrum result: 1 H NMR (400MHz, DMSO) δ8.67 (d, J = 9.0Hz, 1H), 8.58-8.50 (m, 2H), 8.33 (ddd, J = 8.7, 7.1, 1.3Hz, 1H), 8.11 (dd, J=13.4, 5.7Hz, 1H), 4.43(s, 3H), 3.07(s, 3H).

[0073] Compound 1a obtained in Example 1 is analyzed by mass spectrometer, and its mass spectrometry resul...

Embodiment 2

[0074] Embodiment 2: the synthesis of compound 1b

[0075] Weigh 0.4g (1.56mmol) of 2-methylbenzothiazole and 0.4ml (2mmol) of 1,3-dibromopropane into a 25ml round-bottomed flask as a pinkish white solid, heat the mixture to 100°C, and react 12 After one hour, cool, shake after adding ethyl acetate, suction filter, solid is washed with ethyl acetate, weigh after vacuum drying, thin-layer chromatography preliminary shows that there is no by-product, chemical structural formula is as follows, pure product 1b, productive rate is 98.2%.

[0076]

[0077] The compound 1b obtained in Example 2 is analyzed by nuclear magnetic resonance, and its hydrogen nuclear magnetic resonance spectrum result is obtained: 1H NMR (400MHz, DMSO) δ8.67 (d, J=9.0Hz, 1H), 8.57-8.51 (m, 2H), 8.33 (ddd, J = 8.7, 7.1, 1.3 Hz, 1H), 8.12 (t, J = 7.7 Hz, IH), 4.43 (s, 3H), 3.07 (s, 3H).

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 provides a compound and a preparation method and application thereof. The compound serves as a fluorescent probe and can selectively recognize G-quadruplex DNA, and compared with fluorescent probes with similar functions, the probe has the advantages of being high in selectivity, low in biotoxicity, good in membrane permeability, high in color development, good in re-dyeing compatibility and relatively high in light stability. It is indicated that the probe has a wide application range as the G-quadruplex DNA and nucleolus fluorescent probe and is expected to be developed into asimple and visual biological detection reagent related to G-quadruplex DNA and nucleoli and used for physiological and pathology research. The experiment result shows that the compound serves as the fluorescent probe, a fluorescence image marked by the probe has obvious red light distribution when displayed in a cytoplasm and nucleuse area, and it shows that the probe can be used for recognizing specific imaging cytoplasm in living cells and G-quadruplex DNA in the nucleoli.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to a compound and its preparation method and application. Background technique [0002] Small-molecule probes refer to detectors developed for a specific target biomolecule or biological ion. Small-molecule probes can specifically interact with specific target molecules and can be detected by special detection techniques. Compared with ordinary detection technologies, probe technology has the advantages of high sensitivity, strong specificity, fast and accurate, and is suitable for molecular imaging and real-time monitoring. [0003] The G-quadruplex DNA structure is a special secondary structure formed by guanine (G)-rich nucleic acid sequences. As an important part of ribonucleic acid, G-quadruplex DNA makes many biological functions Both are closely related to G-quadruplex DNA, which scientists believe is a potential drug target. Due to the advantages of G-quadruplex DNA fluor...

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): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1037G01N21/6486
Inventor 龙威张焜卢宇靖李莹杜现王聪蔡森源郑园园林丹敏
Owner GUANGDONG UNIV OF TECH
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