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A kind of indole vinyl substituted quinoline derivatives and its preparation method and application

A technology of indolevinyl and quinolines, applied in the field of fluorescent probes, can solve the problems of inability to distinguish G-quadruplex structures, etc.

Active Publication Date: 2020-04-28
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when the currently disclosed fluorescent agents are used for nucleic acid labeling, they cannot distinguish the G-quadruplex structure from other secondary nucleic acid structures

Method used

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  • A kind of indole vinyl substituted quinoline derivatives and its preparation method and application
  • A kind of indole vinyl substituted quinoline derivatives and its preparation method and application
  • A kind of indole vinyl substituted quinoline derivatives and its preparation method and application

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preparation example Construction

[0054] The present invention also provides a preparation method of indole vinyl substituted quinoline derivatives, comprising:

[0055] Formula (II) compound, formula (III) compound, R 2 -H reaction to obtain indole vinyl substituted quinoline derivatives;

[0056]

[0057] Among them, R 1 , R 3 independently selected from H, halogen, hydroxyl, C1-C6 alkoxy, C2-C15 imino, C1-C6 alkyl;

[0058] R 4 Alkyl group selected from C1~C6;

[0059] R 2 selected from piperidinyl, morpholinyl, pyrrolyl or NR 5 R 6 ;

[0060] R 5 , R 6 independently selected from H, -CH 3 、-CH 2 CH 3 、-CH 2 CH 2 OH, -CH 2 CH 2 CH 2 OH, formula (R-1), formula (R-2), formula (R-3), formula (R-4) or formula (R-5),

[0061] and R 5 , R 6 Not H at the same time.

[0062] According to the present invention, the present invention will formula (II) compound, formula (III) compound, R 2 -H reaction to obtain indolevinyl substituted quinoline derivatives; wherein, the limitation of each...

Embodiment 1

[0074] Embodiment 1: the synthesis of compound 2 (4-chloro-1,2-dimethylquinoline)

[0075] Weigh 0.2g (1.1236mmol) of 4-chloro-2-methylquinoline into a 25ml round bottom flask, add methyl iodide and solvent sulfolane, heat the mixture to 40-60°C, react for 18 hours, cool, add Shake it with anhydrous ether, filter it with suction, wash the solid several times, and weigh it after vacuum drying. Thin-layer chromatography shows that there is no by-product, and 0.345 g of pure product 2 is obtained with a yield of 95.8%.

[0076] 1 H NMR (400MHz, DMSO) δ8.56(d, J=8.4Hz, 1H), 8.46(d, J=8.3Hz, 1H), 8.22(t, J=8.1Hz, 1H), 8.01(t, J =7.9Hz, 1H), 7.55(s, J=7.4Hz, 1H), 4.20(s, 3H), 3.74(s, 1H), 2.68(s, 3H).

Embodiment 2

[0077] Embodiment 2: the synthesis of compound (I-a)

[0078] Weigh 0.0318g (0.001mol) of compound 2 and add it to a round-bottomed flask containing 10ml of ethanol, then add 0.217g, which is 1.5 times the molar amount of indole-2-carboxaldehyde, stir at room temperature for 5 minutes and then add 0.6ml of pyrrole was reacted at 80°C for 5 hours, cooled to room temperature, 10ml of ethyl acetate was added to the reacted solution, suction filtered after shaking, and the precipitate was washed with a small amount of ethanol, and compound (I-a) was obtained after vacuum drying. Brown solid 0.393g, its structure is as follows, the yield is 81.7%.

[0079] 1 H NMR (400MHz, DMSO) δ11.77(s, 1H), 8.51(d, J=8.4Hz, 1H), 8.16(d, J=8.8Hz, 1H), 8.00(t, J=7.8Hz, 1H ), 7.88(d, J=15.8Hz, 1H), 7.67(t, J=7.7Hz, 1H), 7.61(d, J=8.0Hz, 1H), 7.55(d, J=15.8Hz, 1H), 7.44(d, J=8.2Hz, 1H), 7.22(t, J=7.4Hz, 1H), 7.04(dd, J=9.0, 5.4Hz, 2H), 6.92(s, 1H), 4.12(s, 3H ), 3.98 (d, J=31.6Hz, 4H), 2.06 (s, ...

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Abstract

The invention provides an indole ethylene-substituted quinoline derivative with a structure shown in a formula (I). A series of indole ethylene-substituted quinoline derivatives with the structure shown in the formula (I) can be obtained by introducing indole-2-formaldehyde to quinoline site as a parent and selecting special substituent groups. Proofed by experiment results, the indole ethylene-substituted quinoline derivative with the structure shown in the formula (I) has the advantages that when the indole ethylene-substituted quinoline derivative is used as a fluorescent probe, the action force with G-quadruplex is stronger, and the action with other secondary nucleic acids is weaker; specifically, when the fluorescent probe is mixed with different secondary nucleic acids, and the nucleic acid is the G-quadruplex, the specific action with probe molecules can produce the change of fluorescent spectrum; when the secondary structure of the nucleic acid adopts the other structure, the obvious signal change is not produced.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to an indolevinyl-substituted quinoline derivative and a preparation method and application thereof. Background technique [0002] Nucleic acid is not only the basic component of all biological cells, but also plays a dominant 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 at the end of the telomeric region, and the promoter regions of various genes, such as c-kit, c-myc, c-myb, bcl-2 , PD...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/06C09K11/06G01N21/64
CPCC07D401/06C09K11/06C09K2211/1029C09K2211/1033G01N21/6402
Inventor 阎雁王聪卢宇靖郑园园蔡森源龙威
Owner GUANGDONG UNIV OF TECH
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