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2,3-epoxy-2-propyl sulfone-5,8-dimethoxy-1,4-naphthoquinone as well as preparation method thereof, and medicine containing same

A dimethoxy, naphthoquinone technology, applied in the field of medicine, can solve the problems of liver function damage, blood picture reduction, lack of discrimination ability of chemotherapy, etc., and achieve the effect of reducing toxic side effects, low irritation and toxicity, and low normal cytotoxicity

Active Publication Date: 2018-03-13
HEILONGJIANG BAYI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the clinical treatment of cancer is aimed at killing cancer cells, but chemotherapy has no ability to distinguish, and often kills a large number of normal cells while killing cancer cells. Symptoms such as reaction, decreased blood picture, abdominal pain, fever, etc., are the common defects of drugs for the treatment of liver cancer in clinical practice.

Method used

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  • 2,3-epoxy-2-propyl sulfone-5,8-dimethoxy-1,4-naphthoquinone as well as preparation method thereof, and medicine containing same
  • 2,3-epoxy-2-propyl sulfone-5,8-dimethoxy-1,4-naphthoquinone as well as preparation method thereof, and medicine containing same
  • 2,3-epoxy-2-propyl sulfone-5,8-dimethoxy-1,4-naphthoquinone as well as preparation method thereof, and medicine containing same

Examples

Experimental program
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Embodiment

[0054] Example: Preparation of 2,3-epoxy-2-propylsulfone-5,8-dimethoxy-1,4-naphthoquinone compound in this example:

[0055] 1. Synthesis of 2-propylmercapto-5,8-dimethoxy-1,4-naphthoquinone

[0056] In a 100ml reaction bottle, add 218.21mg (1mmol) of 5,8-dimethoxy-1,4-naphthoquinone and 50ml of methanol, mix well, add 111.02μl (1.5mmol) of 1-propanethiol, and react at room temperature for 4 hours Finally, 149.8 mg (0.2 mmol) of sodium dichromate and 27.2 μl (0.75 mmol) of concentrated sulfuric acid were added to the mixture, and the reaction was completed after 5-10 minutes. Extracted with dichloromethane and saturated brine, dried with an appropriate amount of anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain a crude product, which was prepared by column chromatography, 2-propylmercapto-5,8-dimethoxy-1,4- naphthoquinone.

[0057] 2. Synthesis of 2,3-epoxy-2-propylsulfone-5,8-dimethoxy-1,4-naphthoquinone (EPDMNQ)

[0058] In a 50ml reaction bottle, ...

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Abstract

The invention discloses 2,3-epoxy-2-propyl sulfone-5,8-dimethoxy-1,4-naphthoquinone as well as a preparation method thereof, and a medicine containing 2,3-epoxy-2-propyl sulfone-5,8-dimethoxy-1,4-naphthoquinone, and belongs to the technical field of medicines. The structural formula is as shown in the description. The method comprises the following steps: I, dissolving 5,8-dimethoxy-1,4-naphthoquinone in methyl alcohol, adding 1-propyl sulfhydrate for reaction at room temperature, then adding sodium bichromate and concentrated sulfuric acid for continuous reaction, carrying out extraction withdichloromethane and a saturated saline solution, drying the product with anhydrous sodium sulfate, filtering the product, and concentrating the product till the product is dry; II, dissolving the product in chloroform, continuously adding 3-chloroperoxybenzoic acid for reaction at room temperature, adding a NaHCO3 solution at the concentration of 5 percent after the reaction is completed to neutralize surplus metachloroperbenzoic acid in the reaction, then ending the reaction, carrying out extraction with the dichloromethane and the saturated saline solution, drying the product with the anhydrous sodium sulfate, filtering the product, and concentrating the product till the product is dry. The compound and a medicine composition can be applied to preparation of a medicine for treating a liver cancer.

Description

technical field [0001] The invention belongs to the technical field of medicine; in particular, it relates to a 2,3-epoxy-2-propylsulfone-5,8-dimethoxy-1,4-naphthoquinone compound, its preparation method and the compound as an active ingredient pharmaceutical composition. Background technique [0002] The traditional way of new drug development is to develop and research new drugs by using active ingredients in natural products as lead compounds. Comfrey is a traditional Chinese medicine with a long history of medicinal use and extensive pharmacological effects. Its main active ingredient, shikonin, is a lead compound with great potential for development. Naphthoquinone compounds represented by shikonin have various physiological activities such as anti-inflammatory, antibacterial, antiviral, antimalarial, and antitumor. Especially in anti-cancer research, it has been reported that it can inhibit tumor cell growth, induce cell apoptosis, inhibit DNA topoisomerase, inhibit ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/48C07D301/14A61K31/336A61P35/00A61P1/16
CPCC07D301/14C07D303/48
Inventor 金成浩刘香萍王玥孟令旗李金钱王浩王加茹张翼刘畅吴艾秦徐宛婷刘洋李明博卓然李捷瑶韩烁张彤
Owner HEILONGJIANG BAYI AGRICULTURAL UNIVERSITY
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