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Preparation method of 2-butyl sulfoxide-1,4-naphthoquinone

A naphthoquinone and sulfhydryl technology, applied in the field of preparation of 1,4-naphthoquinone, can solve the problems of low reaction yield, reduced anticancer activity, harsh reaction conditions, etc., and achieves simple synthesis route, obvious anticancer effect, The effect of low reaction temperature

Inactive Publication Date: 2016-05-04
HEILONGJIANG BAYI AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0003] However, most of the natural naphthoquinones exist in plants, and the extraction and separation of naphthoquinones from plants alone is far from meeting the needs of research and application. Artificial synthesis or biomimetic synthesis has become one of the important approaches.
In addition, the modification of the structure of naphthoquinone compounds will reduce the toxic and side effects and greatly reduce its anticancer activity. Anti-cancer effect, reducing its toxic and side effects, and improving its selectivity to cancer cells are the key to the synthesis of new naphthoquinone derivatives. Expensive, reagents are too toxic and many other disadvantages, to establish a new synthetic route suitable for large-scale synthesis of naphthoquinone derivatives, and the reaction route is simple and high yield, mass production of high-efficiency and low-toxic naphthoquinone derivatives has a wide range of applications Prospects and Significance

Method used

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  • Preparation method of 2-butyl sulfoxide-1,4-naphthoquinone
  • Preparation method of 2-butyl sulfoxide-1,4-naphthoquinone
  • Preparation method of 2-butyl sulfoxide-1,4-naphthoquinone

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Experimental program
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Embodiment 1

[0025] The following steps are used to prepare 2-butylsulfoxide-1,4-naphthoquinone:

[0026] (1) Synthesis of 2-butylmercapto-1,4-naphthoquinone

[0027] In a 100ml reaction bottle, add 158.15mg (1mmol) of 1,4-naphthoquinone and 30ml of methanol, mix well, add 166μl (1.5mmol) of 1-butanethiol, and react at room temperature for 4 hours, then add dichrome to the mixture Sodium acid 59.6mg (0.2mmol) and concentrated sulfuric acid 40.8μl (0.75mmol), the reaction is completed after 5-10 minutes. Extracted with dichloromethane and saturated saline, dried with an appropriate amount of anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain a crude product, which was prepared by TLC to obtain 2-butylmercapto-1,4-naphthoquinone;

[0028] (2) Synthesis of 2-butylsulfoxide-1,4-naphthoquinone (BSNQ)

[0029] In a 50ml reaction bottle, add 246.32mg (1mmol) of the above-mentioned product 2-butylmercapto-1,4-naphthoquinone and 20ml of chloroform, slowly add 276.1mg (1.2mm...

experiment example

[0031] 1. The killing effect of BSNQ on cancer cells

[0032] Experiment method: (MTT experiment)

[0033] ① Cell inoculation: use culture medium containing 10% fetal calf serum to prepare a single cell suspension, inoculate 10,000 cells per well into a 96-well plate, and the volume of each well is 200 μl;

[0034] ② Culture cells: 5% CO 2 , incubate at 37°C for 24 hours until the cell monolayer covers the bottom of the well;

[0035] ③ Serum starvation: Change the culture medium (culture medium containing 1% FBS) 2 hours before adding the drug;

[0036] ④ Drug treatment: The prepared BSNQ was treated with final concentrations of 0, 1, 3, 10, 30, 40, 50, 60, 70, 80, and 100 μM to treat human liver cancer Hep3B, HepG2, and Huh7 cells for 24 hours;

[0037] ⑤ Color reaction: Add 20 μl of MTT solution (5 mg / ml, prepared in PBS, pH 7.4) to each well. After continuing to incubate for 2-4 hours, carefully aspirate and discard the culture supernatant in the well, carefully wash t...

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Abstract

The invention discloses a preparation method of 2-butyl sulfoxide-1,4-naphthoquinone. The method solves the problem that in the prior art, the requirements of study and application are far from being met when naphthoquinone compounds are extracted and separated only from plants. The preparation method specifically includes the two steps of firstly, synthesizing 2-butyl sulphur-1,4-naphthoquinone, wherein 1-butyl mercaptan and 1,4- naphthoquinone are made to react for 3-5 hours at the room temperature, sodium dichromate and concentrated sulfuric acid are added, the mixture continues to react for 5-10 minutes, and the product is post-processed to obtain 2-butyl sulphur-1,4-naphthoquinone; secondly, synthesizing 2-butyl sulfoxide-1,4-naphthoquinone, wherein 2-butyl sulphur-1,4-naphthoquinone and 3-chloroperoxybenzoic acid react for 1.5-2.5 hours at the temperature of 0 DEG C, and the product is post-processed to obtain 2-butyl sulfoxide-1,4-naphthoquinone. The preparation method is simple in synthesis route and low in reaction temperature, and the obtained product 2-butyl sulfoxide-1,4-naphthoquinone is obvious in anti-cancer effect and high in selectivity to cancer cells.

Description

technical field [0001] The invention relates to a preparation method of 1,4-naphthoquinone. Background technique [0002] With the increasing incidence of cancer year by year, some progress has been made in the etiology and mechanism of tumors and the research and development of anticancer drugs, but there are still many problems to be solved. Finding efficient and safe new anti-tumor drugs has become a research hotspot. In recent years, various physiological activities of naphthoquinones, such as anticancer, anti-inflammatory, antibacterial and antiviral, have attracted the attention of researchers at home and abroad. [0003] However, most of the natural naphthoquinones exist in plants, and the extraction and isolation of naphthoquinones from plants is far from meeting the needs of research and application. Artificial synthesis or biomimetic synthesis has become one of the important approaches. In addition, the modification of the structure of naphthoquinone compounds wi...

Claims

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Application Information

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IPC IPC(8): C07C317/12C07C315/02
CPCC07C319/14C07C315/02
Inventor 金成浩孙虎男罗英花臧延青申贵男刘畅吴丹丹蒋雪园孟令旗王浩徐婉婷
Owner HEILONGJIANG BAYI AGRICULTURAL UNIVERSITY
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