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Fangchinoline derivative with anticancer activity as well as preparation method and application thereof

A technology for fangchinoline base and anticancer activity is applied in the field of fangchinoline base derivatives and preparation, and can solve the problems of low bioavailability and wide application, and achieve the effects of low price of raw materials, novel structure and improved biological activity.

Active Publication Date: 2020-09-18
INST OF AGRO FOOD SCI & TECH SHANDONG ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, natural compounds have their own shortcomings, such as low bioavailability, which limit the wide application in clinical practice. Therefore, the novel structure of antiseptic derivatives, through structural modification to change the structure-activity relationship and strive to overcome its own shortcomings, has become Research hotspots in the field of chemical compounds

Method used

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  • Fangchinoline derivative with anticancer activity as well as preparation method and application thereof
  • Fangchinoline derivative with anticancer activity as well as preparation method and application thereof
  • Fangchinoline derivative with anticancer activity as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0033] The preparation method of fangchinoline base derivatives with anticancer activity, first dissolve 100 mg fangchinoline base dTet (about 0.18 mmol) in 3 mL of dichloromethane, place it in a two-necked flask, and repeatedly inject argon into the flask Gas three times until the air is evacuated to fill the bottle with argon, and the temperature is controlled to 0 °C. Under magnetic stirring, 66.5 mg (about 0.72 mmol) of triethylamine dissolved in 2 mL of dichloromethane was added. After 1 hour of reaction, 50.7 mg (about 0.20 mmol) of 2-bromobenzenesulfonyl chloride was added, and the reaction was tracked by TLC. After the reaction, the reaction solution was concentrated and purified through a neutral alumina column. The eluent was dichloromethane:methanol (120:1, 100:1, 80:1), separated and purified, and the white powder product 123.6 mg (about 0.149 mmol), the yield is 83%. After NMR and HRMS analysis, the obtained product is 7-O-(m-Br-benzenesulfonyl) fangchinoline base...

Embodiment 2

[0039]The preparation method of fangchinoline base derivatives with anticancer activity: 100.0 mg fangchinoline base dTet (about 0.18 mmol) was dissolved in 3 mL of dichloromethane, placed in a two-necked flask filled with argon, controlled Warm to 0°C. Under magnetic stirring, 66.5 mg (about 0.72 mmol) of triethylamine dissolved in 2 mL of dichloromethane was added. After 1 hour of reaction, 38.0 mg (about 0.20 mmol) of p-toluenesulfonyl chloride was added, and the reaction was tracked by TLC. After the reaction, the reaction solution was concentrated and purified through a neutral alumina column. The eluent was dichloromethane:methanol (120:1, 100:1, 80:1), separated and purified to obtain the white powder product 119.5 mg (about 0.157 mmol), the yield is 87%, analyzed by NMR and HRMS, it is 7-O-(p-toluenesulfonyl) fangchinoline base, the NMR spectrum is as follows image 3 and 4 shown.

[0040] 1 H NMR (400 MHz, CDCl 3 ) δ 7.53 (d, J = 8.1 Hz, 2H), 7.36 – 7.20 (m,4...

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Abstract

The invention relates to the technical field of bio-preparation of a fangchinoline derivative, in particular to a fangchinoline derivative with anticancer activity as well as a preparation method andapplication of the fangchinoline derivative. The molecular structure of the fangchinoline derivative is shown in the specification. The novel tetrandrine derivative is synthesized, has an anti-canceractivity effect and is high in activity. The biological activity of the fangchinoline is improved by performing structural modification on the fangchinoline, and the fangchinoline has important practical significance for researching and developing novel anti-cancer drugs. According to the fangchinoline derivative with the anticancer activity, fangchinoline is used as a raw material for related structural modification, the synthesis method is simple, the price of the raw material is low, and the structure is novel.

Description

technical field [0001] The invention relates to the technical field of preparation of fangchinoline derivatives, in particular to a fangchinoline derivative with anticancer activity, a preparation method and an application thereof. Background technique [0002] Cancer is a major public health problem worldwide. Cancer is one of the major public health problems in the world. According to the World Health Organization (WHO) statistical report in 2018, there were about 18.1 million new cancer cases worldwide and 9.6 million patients died of cancer. It is expected that global cancer cases will show a rapid growth trend. This will increase to 19 million by 2025 and 24 million by 2035. The continuous increase in the incidence of cancer globally is also driving the rapid development of the anticancer drugs market. However, fewer and fewer anticancer drugs are currently available due to acquired drug resistance and multiple molecular cancer types. Scientists have investigated man...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/18A61P35/00
CPCC07D491/18A61P35/00
Inventor 孙金月刘超刘玉法陈家树高修正王目旋张瑞瑞
Owner INST OF AGRO FOOD SCI & TECH SHANDONG ACAD OF AGRI SCI
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