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

Cyano furanone derivative fluorescent probe as well as preparation method and application thereof

A technology of cyanofuranone and fluorescent probe, which is applied in the field of chemical detection, can solve the problems of low content and inability to meet the needs of daily life, and achieve the effects of simple synthesis process, reliable performance, high selectivity and sensitivity

Active Publication Date: 2020-05-12
GUANGZHOU UNIVERSITY
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although it exists widely in natural products, its content is very low and cannot meet the needs of daily life. Therefore, most of the current food industry uses artificially synthesized furanone derivatives

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
  • Cyano furanone derivative fluorescent probe as well as preparation method and application thereof
  • Cyano furanone derivative fluorescent probe as well as preparation method and application thereof
  • Cyano furanone derivative fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1. Diethyl 2,2'-((4-(2-(4-cyano-5-(dicyanomethyl)-3,3-dimethyl-2,3-dihydrofuran- Preparation of 2-yl)vinyl)phenyl)ureadiyl)(trans)-diacetate

[0035]

[0036] Step (1): Add 5mmol, 0.60g p-formanilide to 30mL of absolute ethanol to dissolve it fully, add 10mmol, 1.22g ethyl chloroacetate, stir for 30 minutes under ice bath conditions, add 10mmol, 3.26g Cesium carbonate, moved to room temperature and stirred for 5 hours, followed by thin layer chromatography. After the reaction, washed with saturated sodium chloride solution, evaporated under reduced pressure to remove the organic solvent, separated by silica gel column chromatography, and the eluent was petroleum ether A mixed solution composed of ethyl acetate in a volume ratio of 10:1 to obtain a light yellow oily liquid;

[0037] Step (2): Add 5 mmol, 1.00 g of 3-hydroxy-3-methylbutan-2-one into absolute ethanol, add 5 mmol, 0.33 g of malononitrile, stir for 20 minutes under ice bath conditions, add 5 mmol...

Embodiment 2

[0040] Example 2. Diethyl 2,2'-((4-(2-(4-cyano-5-(dicyanomethyl)-3,3-dimethyl-2,3-dihydrofuran- Preparation of 2-yl)vinyl)phenyl)ureadiyl)(trans)-dicarboxylate

[0041]

[0042] The difference between the preparation method of Example 2 of the present invention and Example 1 is that the raw material methyl chloroacetate is used to replace ethyl chloroacetate, and the remaining parameters are the same as in Example 1. The preparation method obtains the target compound as a yellow powder, and the yield is 68%. .

[0043] 1 H NMR (600MHz, DMSO-d 6 )δ7.65(d, J=8.7Hz, 2H), 7.45(d, J=8.7Hz, 2H), 6.74(d, J=9.9Hz, 1H), 6.56(dd, J=9.0, 3.0Hz, 1H),4.40(s,1H),4.29(s,4H),4.17(s,1H),3.63(s,6H),1.02(s,6H).HRMS(ESI-TOF)m / z:[M +H] + Calcd for C 24 h 25 N 4 o 5 449.1824, Found 449.1822.

Embodiment 3

[0044] Example 3: Diethyl 2,2'-((4-(2-(4-cyano-5-(dicyanomethyl)-3,3-dimethyl-2,3-dihydrofuran- Preparation of 2-yl)vinyl)phenyl)ureadiyl)(trans)-dicarboxylic acid

[0045]

[0046] The difference between the preparation method of Example 3 of the present invention and Example 1 is that the raw material chloroacetic acid is used instead of ethyl chloroacetate, and the remaining parameters are the same as in Example 1. This preparation method obtains the target compound as a yellow powder, and the yield is 62%.

[0047] 1 H NMR (600MHz, DMSO-d 6 )δ12.04(s, 2H), 7.67(d, J=8.7Hz, 2H), 7.48(d, J=8.8Hz, 2H), 6.74(d, J=9.7Hz, 1H), 6.57(dd, J=8.7,2.7Hz,1H),4.41(s,1H),4.29(s,4H),4.20(s,1H),1.03(s,6H).HRMS(ESI-TOF)m / z:[M +H] + Calcd for C 22 h 21 N 4 o 5 421.1512, Found 421.1511.

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 cyano furanone derivative fluorescent probe as well as a preparation method and application thereof. The fluorescent probe has the structure represented as the specification,wherein the R is selected from the following structural formula; the cyano furanone derivative fluorescent probe disclosed by the invention is reliable in performance and simple in synthesis process,and is used as a probe for detecting the concentration of calcium ions in environment and biological samples, the detection process is not interfered by other cations, and the cyano furanone derivative fluorescent probe has high selectivity on the calcium ions; besides, the fluorescent probe can be used for detecting the fluorescence intensity of the fluorescent probe by modifying the length of the contained R group aliphatic chain. Compared with the prior art, the probe has the advantages that lipid-water distribution can be adjusted; meanwhile, due to the fact that the cyano furanone fluorophore has two properties of color development and fluorescence, the probe can perform double-index detection through absorption and fluorescence, and has important scientific significance in diagnosisof calcium ion related diseases such as hypercalcemia and multiple myeloma.

Description

technical field [0001] The invention belongs to the technical field of chemical detection, and in particular relates to a fluorescent probe of cyanofuranone derivatives and a preparation method and application thereof. Background technique [0002] Natural furanone exists in oats, cheese, cocoa, tea, malt, grapes, beef and pineapples, and was first isolated in 1965 from the ether extract of pineapple juice. Furanone is widely used in the food industry. It is a food spice that can be used according to the national standard. It is also a safe spice approved by the American Daily Flavor and Fragrance Association and the European Spice Council. It has obvious flavor-enhancing effect and low concentration It can greatly enhance the fragrance and can be used in food, tobacco and beverages. Although it exists widely in natural products, its content is very low and cannot meet the needs of daily life. Therefore, artificially synthesized furanone derivatives are mostly used in the f...

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): C07D307/30C09K11/06G01N21/64
CPCC07D307/30C09K11/06G01N21/6428G01N21/6402C09K2211/1007C09K2211/1088
Inventor 陈鲲蔡银怡罗嘉仪雪燕杨雨顺朱海亮
Owner GUANGZHOU UNIVERSITY
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