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A kind of indole compound and its preparation method and application

A technology of compounds and indoles, applied in the field of medicinal chemistry, can solve the problem of few ligands, and achieve the effect of strong binding constant, high fluorescence intensity and low detection limit

Active Publication Date: 2022-03-25
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, many G-quadruplex fluorescent ligands have been developed, but most of them are fluorescent ligands targeting G-quadruplex in the nucleus, and few ligands have been developed for mitochondrial G-quadruplex

Method used

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  • A kind of indole compound and its preparation method and application
  • A kind of indole compound and its preparation method and application
  • A kind of indole compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] The preparation of the indole compound BYM described in this example comprises the following steps:

[0059] (1) Weigh 0.4g (1.912mM) of 1,1,2-trimethyl-1H-benzo[e]indole in an explosion-proof bottle, 4mL (42mM) sulfolane as a solvent, and mix the two with ultrasound Evenly, add 1,1,2-trimethyl-1H-benzo[e]indole twice the molar amount (3.824mM) of methyl iodide under fume hood conditions, place the reaction system in an oil bath and open Magnetic stirring, the reaction temperature is 60°C, and the reaction time is 24 hours; after the reaction system is cooled to room temperature, add a small amount of ethyl acetate to fully shake, let it stand for a while, precipitate crystals, vacuum filter, rinse the filter cake with ethyl acetate, and dry Obtain light yellow crystal intermediate A 1 0.58g, thin plate chromatography shows no by-product, intermediate A 1 The crude yield is 86%;

[0060] The intermediate A 1 The synthetic route of is as follows:

[0061]

[006...

Embodiment 2

[0068] The preparation of the indole compound BYP described in this example comprises the following steps:

[0069] (1) the intermediate A 1 The preparation method is identical with embodiment 1;

[0070] (2) Weigh 0.2g (0.569mM) of Intermediate A 1 and 0.140mg (0.683mM) 4-(4-methylpiperazine) benzaldehyde was placed in an explosion-proof bottle, 3mL (34.25mM) ethanol was used as a solvent, and ultrasonication was used for a while to make the mixture uniform, and the reaction system was placed in an oil bath and Turn on the magnetic stirring, the reaction temperature is 60°C, and the reaction time is 12 hours; after the reaction system is cooled to room temperature, solids will precipitate out, and the dark pink powder is obtained by suction filtration, and then the components in the red powder are separated by column chromatography , finally obtained 0.240 g of indole compounds, counted as BYP, and the yield was 35%. The indole compound BYP is a dark red crystal. The hydr...

Embodiment 3

[0076] The preparation of the indole compound YM described in this embodiment comprises the following steps:

[0077](1) Weigh 0.4g (2.480mM) of 2,3,3-trimethyl-3H-indole into an explosion-proof bottle, 4mL (42mM) sulfolane as a solvent, ultrasonically mix the two evenly for a while, ventilate Add twice the molar amount (4.96mM) of methyl iodide under hood conditions, place the reaction system in an oil bath and turn on magnetic stirring, the reaction temperature is 60°C, and the reaction time is 24h; after the reaction system is cooled to room temperature, add Ethyl acetate was fully shaken, stood still for a while, crystals were precipitated, vacuum filtered, and the filter cake was rinsed with ethyl acetate, dried to obtain light pink intermediate A 2 Crystal 0.52g, thin plate chromatography showed no by-products, intermediate A 2 The crude yield is 70%;

[0078] The intermediate A 2 The synthetic route of is as follows:

[0079]

[0080] (2) Weigh 0.2g (0.664mM) of ...

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Abstract

The invention discloses an indole compound, a preparation method and application thereof. The invention obtains the indole compound by modifying the indole structure and introducing a styryl group and a nitrogen heterocycle. The structural formula of the indole compounds of the present invention is formula (I), which is a fluorescent ligand that selectively binds to mitochondrial G-quadruplexes. The indole compounds can detect mitochondria and can be used in cell experiments. The method can stain the mitochondria in the cells, and has the advantages of high fluorescence intensity, strong binding constant and low detection limit; the indole compound of the invention has the potential of being developed into mitochondrial function diagnostic reagents and anti-tumor drugs.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to an indole compound and its preparation method and application. Background technique [0002] Mitochondria is an organelle that plays an important role in energy metabolism and cell self-regulation. Its main function is to transfer hydrogen from metabolites through a delivery system composed of various enzymes and coenzymes, and finally combine with oxygen to form water. The metabolic system composed of hydrogen donor, transmitter, hydrogen acceptor and corresponding enzyme system, and the hydrogen acceptor is oxygen, is called the respiratory chain. The respiratory chain is composed of NAD or NADH coenzyme, flavin enzyme, iron-sulfur protein, cytochrome and other parts, and their mutual combination can form complexes I, II, III, IV, V, which play an important role in the electron transfer of the respiratory chain . Cancer cells have vigorous energy metab...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14C07D209/60A61P35/00G01N21/64C09K11/06
CPCC07D209/60C07D209/14A61P35/00G01N21/6428G01N21/6486G01N21/6456C09K11/06C09K2211/1029C09K2211/1033C09K2211/1044G01N2021/6443
Inventor 佘梦婷卢宇靖郑伯鑫龙威洪哲鑫陈泽鑫蔡东鹏
Owner GUANGDONG UNIV OF TECH
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