3-benzothiazole-1-(3-dimethylamino)propyl quinoline-4-ketone derivative, as well as preparation method and application thereof

A technology of benzothiazole and dimethylamino, which is applied in the field of 3-benzothiazole-1-propylquinolin-4-one compounds and their preparation, can solve the problems of structural modification and the like, and achieves structural diversification and similar properties. The effect of better medicinal properties and easy availability of raw materials

Inactive Publication Date: 2018-09-11
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Since the synthetic method developed by the members of the research group can only use existing quinolone drugs and their derivatives as raw materials, they cannot make more structural modifications to the substituents on the 4-quinolinone ring to obtain solubility. Compounds with better and better drug-like properties can improve the possibility that these compounds can be further developed into clinical applications in the later stage

Method used

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  • 3-benzothiazole-1-(3-dimethylamino)propyl quinoline-4-ketone derivative, as well as preparation method and application thereof
  • 3-benzothiazole-1-(3-dimethylamino)propyl quinoline-4-ketone derivative, as well as preparation method and application thereof
  • 3-benzothiazole-1-(3-dimethylamino)propyl quinoline-4-ketone derivative, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Synthesis of 3-(2-benzothiazolyl)-4(1H)-quinolinone (compound 3a).

[0040] Under electromagnetic stirring, add compound 1 o-aminothiophenol and compound 2a to the round bottom flask successively and diphenyl ether, under the protection of nitrogen, heated to 220 ° C with an electric heating mantle, and refluxed for 2 hours; cooled to room temperature, a large amount of solid precipitated, filtered with suction, washed with petroleum ether, and then washed with dichloromethane, and placed the solid at 60 °C in a vacuum oven for 3 h to obtain compound 3a. 3a Yield: 92%; Melting point: >300°C.

[0041]

Embodiment 2

[0042] Example 2 Synthesis of 3-(2-benzothiazolyl)-6-methyl-4(1H)-quinolinone (compound 3b).

[0043] Compound 2b Instead of compound 2a, the synthesis method was the same as in Example 1 to obtain compound 3b. 3b Yield: 90%; Melting point: >300°C.

[0044]

Embodiment 3

[0045] Example 3: Synthesis of 3-(2-benzothiazolyl)-6-methoxy-4(1H)-quinolinone (compound 3c).

[0046]

[0047] Compound 2c Instead of compound 2a, the synthesis method is the same as in Example 1 to obtain compound 3c. 3c Yield: 81%; Melting point: >300°C.

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Abstract

The invention discloses a 3-benzothiazole-1-(3-dimethylamino)propyl quinoline-4-ketone derivative with a general formula (I). The general formula (I) is shown in the description, wherein R is H, halogen, alkyl, an alkoxy group or halogen alkane element. The invention discloses a preparation method of the 3-benzothiazole-1-(3-dimethylamino)propyl quinoline-4-ketone derivative and application to preparation of an antitumor medicament. Experiments show that the 3-benzothiazole-1-(3-dimethylamino)propyl quinoline-4-ketone derivative has high suppression activity for liver tumor cells HepG2, Bel-7402 and Bel-7404, a relatively high suppression rate for the HepG2 liver tumor and relatively good antitumor application prospect, the cycle of the cell HepG2 can be arrested in a G2/M period and the cell HepG2 can be induced to apoptosis.

Description

technical field [0001] The invention relates to the technical fields of organic chemistry and medicinal chemistry, in particular to 3-benzothiazole-1-(3-dimethylamino)propylquinolin-4-one compounds and their preparation methods and applications. Background technique [0002] Liver cancer is one of the cancers with the highest mortality rate. At present, the number of liver cancer patients in the world, especially in China and other developing countries, is increasing year by year, seriously endangering people's lives and health. Therefore, how to develop more efficient and low-toxic anti-hepatoma compounds is a huge challenge for the current medicinal chemistry, organic chemistry and other related workers. [0003] 4-quinolinone compounds have a wide range of biological activities. Among the quinolone antibacterial drugs widely used in clinical practice, most of them belong to 4-quinolinone compounds. In 2009, You Qidong’s research group of China Pharmaceutical University N...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A61P35/00A61P1/16A61K31/4709
CPCA61P1/16A61P35/00C07D417/04
Inventor 苏桂发何国学潘成学袁静梅刘晴晴韦辛未莫冬亮
Owner GUANGXI NORMAL UNIV
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