Artemisinin-chlorambucil ester compound and preparation method thereof

A technology of chlorambucil and chlorambucil, which is applied in the field of artemisinin-chlorambucil synthesis and its preparation, can solve the problems of severe toxic and side effects, achieve low toxic and side effects, reduce Toxic and side effects, strong anti-tumor activity

Pending Publication Date: 2021-06-08
江苏德信辰科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although chlorambucil has strong antitumor activity, it has relatively large toxic and side effects. How to reduce its toxic and side effects and enhance the antitumor effect has become an urgent problem to be solved in the industry

Method used

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  • Artemisinin-chlorambucil ester compound and preparation method thereof
  • Artemisinin-chlorambucil ester compound and preparation method thereof
  • Artemisinin-chlorambucil ester compound and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1 prepares artemisinin-chlorambucil compound

[0021] 1.1 Main instruments and reagents

[0022] Agilent-400M nuclear magnetic resonance instrument (CDCl 3 as solvent, TMS as internal standard, U.S. Agilent Company); Agilent Agilent Accurate-Mass-Q-TOF-MS 6520 mass spectrometer (HRMS-ESI, U.S. Agilent Company); BD FACSCalibur flow cytometer (U.S. Becton-Dickinson company).

[0023] K562 human leukemia cells (Nanjing Kebai Biotechnology Co., Ltd.); K562 / ADR human leukemia cells resistant to doxorubicin (Jiangsu Kaiji Biotechnology Co., Ltd.); dihydroartemisinin, chlorambucil, EDCI, DMAP (Saen Chemical Technology (Shanghai) Co., Ltd.); column chromatography and thin-layer silica gel plate (Qingdao Ocean Chemical Factory); other reagents used were of analytical grade, purchased from Shanghai Titan Technology Co., Ltd.

[0024] 1.2 Synthesis method

[0025] In a 10mL eggplant-shaped bottle, dihydroartemisinin (0.35mmol, 1eq), chlorambucil (1.3eq) and DMAP (3e...

Embodiment 2

[0028] Embodiment 2 The effect of artemisinin-chlorambucil compound

[0029] 2.1 In vitro anti-tumor activity test

[0030] With doxorubicin as the positive drug, the cytotoxic activity of the target compound on K562 and K562 / ADR was tested by CCK-8 method. Cells were seeded in 96-well plates in 5% CO 2 and incubated at 37°C for 24 hours. Culture media containing different concentrations of compounds were added respectively, and a negative control group was set up at the same time. After incubation for 72 hours, 10 μL of CCK-8 was added to each well, and the culture was continued for 3 hours in the incubator. λ=450nm, read the absorbance value (OD) of each well with a microplate reader, and calculate the inhibition rate. Statistical software SPSS17.0 calculated the half inhibitory concentration (IC 50 )value. The experiment was repeated three times.

[0031] Taking doxorubicin as the positive drug, the in vitro anti-proliferation activity of the new artemisinin-chloramb...

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Abstract

The invention belongs to the technical field of artemisinin derivatives, and particularly relates to an artemisinin-chlorambucil ester compound and a preparation method thereof. In order to solve the problems that the tumor effect of artemisinin needs to be improved, the toxic and side effects of chlorambucil are large and the like, artemisinin-chlorambucil ester with a novel structure is designed and synthesized according to a pharmacophore splicing principle, and the structure of the artemisinin-chlorambucil ester compound is represented and determined by 1H NMR, 13C NMR and HRMS-ESI. The compound has good anti-tumor activity, and the toxic and side effects of chlorambucil are reduced. The preparation method is simple, the obtained derivative is high in anti-tumor activity and low in toxic and side effects, a novel medicine is provided for tumor resistance, and the derivative has good application value.

Description

technical field [0001] The invention belongs to the technical field of artemisinin derivatives, in particular to an artemisinin-chlorambucil compound and a preparation method thereof. Background technique [0002] Artemisinin is a natural product of sesquiterpene lactones isolated from Artemisia annua of Compositae, and its structure contains a unique peroxy bridge structure. Studies have shown that artemisinin has a variety of important pharmacological activities, such as insect resistance, anti-tumor and anti-inflammation. Due to the poor pharmacokinetic properties of artemisinin, people have done a lot of derivation and modification of its structure, and a variety of artemisinin derivatives are used in clinical antimalarial treatment, such as artemether, artesunate, etc. Drugs can effectively reduce the mortality rate of malaria patients and save the lives of tens of thousands of patients. Chinese scientist Tu Youyou won the 2015 Nobel Prize in Physiology or Medicine fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20A61P35/00A61K31/366A61K31/196A61K47/55
CPCA61K31/196A61K31/366A61K47/55A61P35/00C07B2200/07C07D493/20A61K2300/00
Inventor 徐志刘民赵诗佳
Owner 江苏德信辰科技有限公司
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