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Sertraline side chain amino structure derivative as well as preparation method and application thereof

A technology of chain amino and sertraline, applied in the field of medicine, can solve problems such as chemotherapeutic drug resistance

Active Publication Date: 2021-04-16
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The object of the present invention is to prepare sertraline derivatives by modifying the side chain of sertraline, and the sertraline derivatives have a sensitizing effect when used in drug-resistant gastric cancer cells, so as to solve the problem of tumors in the current gastric cancer treatment. Cells have problems with 'resistance' to chemotherapy drugs

Method used

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  • Sertraline side chain amino structure derivative as well as preparation method and application thereof
  • Sertraline side chain amino structure derivative as well as preparation method and application thereof
  • Sertraline side chain amino structure derivative as well as preparation method and application thereof

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Embodiment 1

[0048] Embodiment 1: the synthesis of compound

[0049] According to the synthesis process of sertraline side chain amino structure derivatives of the present invention figure 1 As shown, weigh compound 1 and aluminum trichloride in a three-necked flask, under N 2Add compound 2 to it under protected conditions, and raise the temperature to 100°C to react for 2.5 hours. After the reaction is complete, cool to room temperature and quench with a mixture of 1N hydrochloric acid and ice, then extract with dichloromethane, and then carry out conventional water removal operations , after being spin-dried, carry out column chromatography separation to obtain the intermediate compound; the equivalent ratio of compound 1 to aluminum trichloride and compound 2 is: 1:8.157 ～ 1:1:2.5.

[0050] 1, the synthetic method of the sertraline derivative shown in formula I

[0051]

[0052] The intermediate compound III was dissolved in isopropanol solution, N 2 Add the modifying group compo...

Embodiment 2

[0065] The synthesis of embodiment 2 numbering NO.1 sertraline derivatives

[0066] The weighed intermediate compound III (583.9mg (2mmol)) was placed in a dry three-necked round-bottomed flask with a stirring bar, and anhydrous and anaerobic treatment was carried out, and then n-propylamine (0.33ml (4mmol)) was added thereto and stirred for 5 Minutes later, tetraisopropyl titanate (2ml (6.75mmol)) was added thereto and refluxed in an oil bath at 85 degrees Celsius for 2 hours. After 2 hours, it was cooled to room temperature and then sodium cyanoborohydride was added thereto. (314.2mg (5mmol)) and heated to 85°C and refluxed until the reaction was complete. After the reaction is complete, the reaction solution is cooled to room temperature, and then quenched by adding an appropriate amount of saturated sodium bicarbonate solution, then extracted with dichloromethane, dried with anhydrous sodium sulfate, suction filtered, and spin-dried to obtain Yellow oil; followed by colum...

Embodiment 3

[0069] Synthesis of embodiment 3 numbering NO.22 sertraline derivatives

[0070] Put the weighed intermediate compound III (583.9mg (2mmol)) in a dry three-neck round-bottomed flask with a stirring bar, carry out anhydrous and anaerobic treatment, and then add Boc-protected ethylenediamine (0.65ml (4mmol) )) After stirring for 5 minutes, tetraisopropyl titanate (2ml (6.75mmol)) was added thereto and refluxed in an oil bath at 85°C for 2 hours. After 2 hours, it was cooled to room temperature and then cyanogen was added thereto. Sodium borohydride (314.2 mg (5 mmol)) was heated to 85 degrees Celsius and refluxed until the reaction was complete. After the reaction is complete, the reaction solution is cooled to room temperature, and then quenched by adding an appropriate amount of saturated sodium bicarbonate solution, then extracted with dichloromethane, dried with anhydrous sodium sulfate, suction filtered, and spin-dried to obtain Yellow oil; then separated by column chromat...

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Abstract

The structural formula of the sertraline side chain amino structure derivative is shown as a formula I or a formula II, wherein R1 is H or cyclopropanyl, and R2 is selected from alkyl, naphthyl, alkylamine, cyclopropanyl, phenyl, or phenyl of which the No.3 position and / or the No.4 position is substituted by alkyl, methoxyalkyl, haloalkyl and halogen; and R3 is a hydrogen group or a 1-halogenated alkyl group. The invention also provides a preparation method of the sertraline derivative and application of the sertraline derivative in preparation of a medicine for treating gastric cancer. The sertraline derivative provided by the invention has an obvious sensitization effect on drug-resistant gastric cancer cells.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to a derivative of sertraline side chain amino structure and its preparation method and application. Background technique [0002] Sertraline is a selective serotonin reuptake inhibitor. In addition to its application in depression, reports on its application value in tumor treatment have also increased significantly in recent years. For example, sertraline has been reported to induce ER calcium release in human prostate cancer cell PC3. In addition, sertraline interacts with and reduces cellular levels of translationally controlled oncoproteins, resulting in decreased migratory properties and colony-forming ability of melanoma cells. In 2018, Xiufeng Pang's research group confirmed the role of sertraline in the treatment of non-small cell lung cancer (NSCLC) in the article "Reuse of sertraline sensitizes non-small cell lung cancer cells to erlotinib by inducing autophagy". Effec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/08C07C217/58C07C209/62C07C209/28C07C211/42
CPCY02P20/55
Inventor 欧阳勤母超古晶郭春伶
Owner ARMY MEDICAL UNIV
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