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Quinoline aromatic ethylene derivative and applications in preparation of fluorescent dyes and fluorescent probes

A quinoline aromatic vinyl, fluorescent dye technology, applied in styryl dyes, fluorescence/phosphorescence, luminescent materials, etc., can solve problems such as small injection volume, achieve low detection limit, low biological toxicity and phototoxicity, fluorescence intensity Enhanced effect

Active Publication Date: 2019-12-31
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] With the development of biotechnology, the previous method of sequencing DNA molecules through isotope effects can no longer meet the requirements; and fluorescent labeling is a labeling technology with the advantages of fast detection speed, good repeatability, small injection volume, and no radiation. Received extensive attention and achieved rapid development

Method used

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  • Quinoline aromatic ethylene derivative and applications in preparation of fluorescent dyes and fluorescent probes
  • Quinoline aromatic ethylene derivative and applications in preparation of fluorescent dyes and fluorescent probes
  • Quinoline aromatic ethylene derivative and applications in preparation of fluorescent dyes and fluorescent probes

Examples

Experimental program
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Effect test

Embodiment 1

[0052] (1) Dissolve 0.40g (2.28mmol) of 2-methylquinoline in 2.2ml (23.1mmol) of sulfolane, then add dropwise 0.42ml (6.84mmol) of methyl iodide, and then stir at 50°C for 2h; after the reaction After cooling, the reaction solution was poured into 15 mL of ethyl acetate and left to stand, filtered under reduced pressure to obtain the crude product; the crude product was washed with ethyl acetate to obtain 0.53 g of the intermediate product I (1,2-dimethyl-1-iodo Quinoline), the yield is 83%. Its proton nuclear magnetic resonance spectrum results are as follows: 1H NMR (400MHz, DMSO) δ9.13 (d, J = 8.6Hz, 1H), 8.61 (d, J = 9.0Hz, 1H), 8.42 (d, J = 8.0Hz, 1H), 8.27–8.20(m, 1H), 8.15(d, J=8.6Hz, 1H), 8.00(t, J=7.6Hz, 1H), 4.47(s, 3H), 3.12(s, 3H). The synthesis process is as follows:

[0053]

[0054] (2) Mix 0.39g (1.385mmol) of the intermediate product I (1,2-dimethyl-1-iodoquinoline) obtained in step (1) with 4mL (43.7mmol) of n-butanol, and then add 0.282 mL (2.077mmol) ...

Embodiment 2

[0061] (1) Dissolve 0.40g (2.28mmol) of 2-methylquinoline in 2.7mL (28.5mmol) of sulfolane, then dropwise add 0.50mL (8mmol) of methyl iodide, then stir at 60°C for 3h; cool down after the reaction , and then the reaction solution was poured into 24mL of ethyl acetate and left to stand, filtered under reduced pressure to obtain the crude product; the crude product was washed with ethyl acetate to obtain 0.58g of the intermediate product I (1,2-dimethyl-1-iodoquinone phenoline), the yield was 89%. Its proton nuclear magnetic resonance spectrum result is the same as embodiment 1 with synthetic process.

[0062] (2) Mix 0.39g (1.385mmol) of the intermediate product I (1,2-dimethyl-1-iodoquinoline) obtained in step (1) with 4.5mL (49.16mmol) of n-butanol, and then add 0.330mL (2.077mmol) of p-dimethylaminobenzaldehyde and 0.21mL (1.25mmol) of 4-methylpiperidine, then stirred at 45°C for 6.5h; The solid was suction-filtered under reduced pressure to obtain 0.52 g of intermediate ...

Embodiment 3

[0066] (1) Dissolve 0.40g (2.28mmol) of 2-methylquinoline in 3.2mL (34mmol) of sulfolane, then add dropwise 0.57mL (9.12mmol) of methyl iodide, and then stir at 70°C for 4h. Cool after the reaction, then pour the reaction solution into 40mL ethyl acetate and let it stand, filter under reduced pressure to obtain the crude product, wash the crude product with ethyl acetate to obtain 0.57g of the intermediate product I (1,2-dimethyl-1- iodoquinoline), the yield is 87%. Its proton nuclear magnetic resonance spectrum result is the same as embodiment 1 with synthetic process.

[0067] (2) Mix 0.39g (1.385mmol) of the intermediate product I (1,2-dimethyl-1-iodoquinoline) obtained in step (1) with 5.1mL (55.4mmol) of n-butanol, and then add 0.376mL (2.77mmol) of p-dimethylaminobenzaldehyde and 0.23mL (1.385mmol) of 4-methylpiperidine, then stirred at 60°C for 8h; after the reaction, 30mL of petroleum ether was added to the reaction solution, and the solid was precipitated after stand...

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Abstract

The invention relates to the technical field of nucleic acid detection, particularly to a quinoline aromatic ethylene derivative and applications in preparation of fluorescent dyes and fluorescent probes, wherein the quinoline aromatic ethylene derivative is a compound represented by a formula I or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer, a tautomer or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer of the compound represented by the formula I or the pharmaceutically acceptable salt thereof according to any ratios, wherein the derivative comprises a racemic mixture. According to the invention, the compound is simple in preparation method, has high fluorescence response to nucleic acid, hascharacteristics of low biotoxicity, low phototoxicity, good water solubility and good cell permeability, has strong binding constant and low detection limit in the field of detection, and can be usedin the preparation of fluorescent dyes and fluorescent probes.

Description

technical field [0001] The invention relates to the technical field of nucleic acid detection, in particular to a quinoline aromatic vinyl derivative and its application in the preparation of fluorescent dyes and fluorescent probes. Background technique [0002] Nucleic acid is not only the basic component of all biological cells, but also plays an important role in the growth, development, reproduction, inheritance and variation of organisms and other major life phenomena. Nucleic acid macromolecules are divided into two categories: deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), which play a role in storing and transmitting genetic information in the replication and synthesis of proteins. [0003] G-quadruplex (G-quadruplex) is a special nucleic acid secondary structure. Many guanine-rich regions in the human genome have the ability to form this structure, including the guanine repeat sequence at the end of the telomeric, and the promoter regions of various genes,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/12C09K11/06C09B23/14G01N21/64
CPCC07D215/12C09K11/06C09B23/145G01N21/6428G01N21/6458
Inventor 佘梦婷卢宇靖黄玄贺郑伯鑫龙威李莹陈翠翠
Owner GUANGDONG UNIV OF TECH
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