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A kind of 2-indol-3-yl-quinoline compound with antitumor activity and its preparation method and application

A technology of compounds and quinolines, which is applied in the field of 2-indol-3-yl-quinolines and their preparation, can solve the problems of cumbersome operation steps, low economic efficiency of atoms and steps, and achieve cheap and easy raw materials. High yield, novel structure, less by-products

Active Publication Date: 2021-01-26
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The carbon-carbon bond coupling between two nitrogen heterocyclic compounds has always been a hotspot and difficulty in the field of organic research. Most of the dinitroheterocyclic skeleton molecules with relatively complex structures must undergo many steps of reactions before they can be synthesized. Not only the operation steps are extremely cumbersome, but also Low atom and step economy

Method used

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  • A kind of 2-indol-3-yl-quinoline compound with antitumor activity and its preparation method and application
  • A kind of 2-indol-3-yl-quinoline compound with antitumor activity and its preparation method and application
  • A kind of 2-indol-3-yl-quinoline compound with antitumor activity and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Mix 1.0 mmol tetrahydroquinoline, 0.5 mmol indole, cuprous chloride with tetrahydroquinoline quality 10%, trifluoromethanesulfonic acid and 2.5ml toluene with tetrahydroquinoline quality 50%, and mix under oxygen condition Stir the reaction at 80°C for 5 hours, cool to room temperature after the reaction, dilute the reaction solution, filter, take the filtrate, and remove the solvent by rotary evaporation under reduced pressure to obtain the crude product, which is purified by column chromatography to obtain the product 1a, the product It is a yellow solid with a yield of 84% and a purity of 97%.

[0060] The preparation route is:

[0061]

[0062] The structural characterization data of the obtained product 1a are as follows:

[0063] 1 H NMR (400MHz, CDCl 3 )δ8.78(s,1H),8.62(d,J=7.8Hz,1H),8.11(d,J=8.4Hz,1H),8.03(d,J=8.6Hz,1H),7.82–7.66( m,3H),7.62(t,J=7.6Hz,1H),7.39(t,J=7.4Hz,1H),7.28(d,J=7.7Hz,1H),7.24–7.14(m,2H);

[0064] 13 C NMR (101MHz, CDCl 3 )δ155.13,...

Embodiment 2

[0068] 0.9 mmol 6-methyltetrahydroquinoline, 0.5 mmol indole, 6-methyltetrahydroquinoline quality 20% copper chloride, 6-methyltetrahydroquinoline quality 60% methanesulfonic acid Mix with 2.0ml of toluene, stir and react at 160°C under oxygen for 5 hours, cool to room temperature after the reaction, dilute the reaction solution, filter, take the filtrate, and remove the solvent by rotary evaporation under reduced pressure to obtain the crude product, which is passed through the column Chromatographic purification yielded product 2a as a yellow solid with a yield of 88% and a purity of 97%.

[0069] The preparation route is:

[0070]

[0071] The structural characterization data of the resulting product 2a are as follows:

[0072] 1 H NMR (400MHz, DMSO) δ11.66(s, 1H), 8.98–8.89(m, 1H), 8.32(s, 1H), 8.12(d, J=8.6Hz, 1H), 8.00(d, J= 8.6Hz, 1H), 7.96(d, J=8.5Hz, 1H), 7.60(s, 1H), 7.56–7.48(m, 2H), 7.24(dd, J=4.9, 2.0Hz, 2H), 2.46( s,3H);

[0073] 13 C NMR (101MHz, DMSO) ...

Embodiment 3

[0077] 0.75 mmol 7-methyltetrahydroquinoline, 0.5 mmol indole, 7-methyltetrahydroquinoline quality 20% copper acetate, 7-methyltetrahydroquinoline quality 10% p-toluenesulfonic acid Mix with 1.5ml of toluene, stir and react at 130°C under oxygen for 10 hours, cool to room temperature after the reaction, dilute the reaction solution, filter, take the filtrate, and remove the solvent by rotary evaporation under reduced pressure to obtain the crude product, which is passed through the column Chromatographic purification yielded product 3a as a yellow solid with a yield of 85% and a purity of 97%.

[0078] The preparation route is:

[0079]

[0080] The structural characterization data of the obtained product 3a are as follows:

[0081] 1 H NMR(400MHz,DMSO)δ11.72(s,1H),8.96(dd,J=5.7,2.9Hz,1H),8.34(s,1H),8.17(d,J=8.6Hz,1H),7.98 (d,J=8.6Hz,1H),7.88(s,1H),7.75(d,J=8.2Hz,1H),7.54(dd,J=5.8,2.8Hz,1H),7.30(d,J= 8.2Hz, 1H), 7.26(dd, J=5.8, 2.8Hz, 2H), 2.54(s, 3H);

[0082] 13 C N...

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Abstract

The invention discloses a 2-indole-3-yl-quinoline compound with anti-tumor activity and its preparation method and application. The preparation route of the 2-indole-3-yl-quinoline compound is as follows : where, R 1 and R 2 Independently selected from hydrogen, hydrocarbon group, methoxy group, ester group or halogen substituent, tetrahydroquinoline compound, indole compound, metal catalyst, acid and solvent react under oxygen conditions to obtain 2-indole-3- Base-quinoline compounds have good inhibitory effects on K562 tumor cells and HeLa cells, and are expected to be used in drugs for preventing and treating tumors.

Description

technical field [0001] The invention belongs to the field of synthesizing functionalized diazaheterocyclic compounds, and in particular relates to a 2-indol-3-yl-quinoline compound with antitumor activity and its preparation method and application. Background technique [0002] Nitrogen-containing heterocyclic compounds are a very important class of organic heterocyclic compounds, which play a very important role in human life. With the development of society, nitrogen-containing heterocyclic compounds have fully demonstrated their superior physiological activity and medicinal value, and have been widely studied and applied in the fields of bioengineering, material science, medicinal chemistry, organic synthesis and natural product chemistry. . Therefore, the synthesis of nitrogen heterocyclic compounds is becoming more and more important. Among a wide variety of nitrogen-containing heterocyclic compounds, quinolines and indoles generally have unique biological activities ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04A61P35/00
CPCA61P35/00C07D401/04
Inventor 邵佳新杨志海陈修文郭子茵张子萍宋俊楠
Owner WUYI UNIV