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Compound synthesized from targeting antitumor drug F16 and chlorambucil, and preparation method thereof

An anti-tumor drug, chlorambucil technology, applied in anti-tumor drugs, drug combinations, organic chemistry, etc., can solve the problems of multi-drug resistance and low selectivity of anti-cancer drugs

Inactive Publication Date: 2017-01-04
CHANGSHA HOOZ BIOSCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In order to overcome the problems of the prior art, the present invention provides a compound synthesized by targeted antineoplastic drug F16 and chlorambucil and a preparation method thereof, which treats cancer with mitochondria as the target, and overcomes the low selectivity and multiplicity of anticancer drugs. The problem of drug resistance, to achieve the effect of clearing cancer cells through apoptosis

Method used

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  • Compound synthesized from targeting antitumor drug F16 and chlorambucil, and preparation method thereof
  • Compound synthesized from targeting antitumor drug F16 and chlorambucil, and preparation method thereof
  • Compound synthesized from targeting antitumor drug F16 and chlorambucil, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] First, get compound 1 (3-bromopropylamine hydrobromide) and 4-picoline reaction, compound 1 structure is as follows:

[0081]

[0082] During specific implementation, respectively add 4-picoline (2g), 3-bromopropylamine hydrobromide (1.0eq), 10ml of anhydrous methanol (or absolute ethanol, anhydrous ether) in the reaction flask, then heat to reflux React overnight. After the reaction was complete, the reaction system was cooled to room temperature, filtered, washed with a small amount of methanol, and dried to obtain a white solid, namely compound 2 (5.0 g); in this example, the structure of compound 2 was as follows:

[0083]

[0084] Next, add compound 2 (2.27g), 20ml of tetrahydrofuran, 20ml of anhydrous sodium carbonate (2.0eq) dissolved in water, stir at room temperature for 30min, then slowly add di-tert-butyl dicarbonate (1.1eq) dropwise into the reaction flask In 10ml of tetrahydrofuran, react at 25-30°C for 4 hours. Filtrate, spin the filtrate to drynes...

Embodiment 2

[0097] The method for preparing compound 3 is the same as that in Example 1, and will not be repeated here.

[0098] Get compound 3 and compound 9 (6-fluoroindole-3-formaldehyde) reaction,

[0099]

[0100] The specific steps are: respectively add compound 3 (1.0g), 6-fluoroindole-3-carbaldehyde (1.0eq), and anhydrous methanol 30ml into the reaction flask, then add piperidine (0.9eq), and heat up to 50°C After the reaction was completed overnight, the reaction system was spun dry and passed through the column, then an appropriate volume of dichloromethane and methanol (35:1) was added for stirring, and then filtered, and the filtrate was spun dry again to obtain a deep red semi-solid compound 10 (0.7g), the structure of compound 10 is as follows:

[0101]

[0102]

[0103] Then, compound 10 (0.5 g), 5 ml of methanol (or ethanol, ether) were added into the reaction flask, 2.5 ml of concentrated hydrochloric acid was added dropwise at room temperature, and the reaction...

Embodiment 3

[0108] The method of preparing compound 3 is the same as that in Example 1, and will not be repeated here.

[0109] Get compound 3 and compound 13 (5-fluoroindole-3-formaldehyde) reaction,

[0110]

[0111] The specific steps are: respectively add compound 3 (1.0g), 5-fluoroindole-3-carbaldehyde (1.0eq), and anhydrous methanol 30ml into the reaction flask, then add piperidine (0.9eq), and heat up to 50°C React overnight. The reaction was complete, the reaction system was spin-dried and passed through the column, then an appropriate volume of dichloromethane and methanol (25:1) was added to stir, and then filtered, and the filtrate was spin-dried again to obtain a dark red semi-solid compound 14 (0.75g ), the structure of compound 14 is shown below:

[0112]

[0113] Subsequently, compound 14 (0.5 g) and 5 ml of methanol were added to the reaction flask, 2.5 ml of concentrated hydrochloric acid was added dropwise at room temperature, and reacted at room temperature for ...

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Abstract

The invention provides a compound synthesized from a targeting antitumor drug F16 and chlorambucil, and a synthesis route and preparation method for the compound. The compound uses mitochondria as a target for treatment of cancers, overcomes the problems of low selectivity and multi-drug resistance of antitumor drugs and achieves the effect of removal of cancer cells through cell apoptosis.

Description

[0001] 【Technical field】 [0002] The invention relates to an antitumor drug compound, in particular to a compound targeting antitumor drug F16 and chlorambucil and a preparation method thereof. [0003] 【Background technique】 [0004] Cancer is a chronic disease that seriously endangers human health, and has become the second largest killer after cardiovascular disease. Therefore, it is of great significance to find anti-tumor drugs and study their mechanism of action. [0005] Mitochondria are important organelles in cells and play an important role in cell metabolism. They are the "energy factory" of living organisms and participate in various metabolic processes such as energy production, apoptosis, and canceration. Changes in mitochondrial structure and function will not only interfere with cell growth, metabolism and proliferation, but also cause apoptosis. Therefore, the research and development of new anti-tumor drugs targeting mitochondria has become a major research ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06A61P35/00
CPCC07D401/06
Inventor 谢国建刘文沛彭咏波吴长兴冯德哲谭蔚泓
Owner CHANGSHA HOOZ BIOSCI & TECH CO LTD
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