2-octyl sulfoxide-1,4-naphthoquinone compound

The technology of a compound, octyl sulfoxide, is applied in the field of new compounds to achieve superior anticancer activity

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

AI Technical Summary

Problems solved by technology

[0003] In recent years, the research on naphthoquinones has mainly focused on 2- or 6-substituted 5,8-dihydroxy 1,4-naphthoquinone and 5,8-dimethoxy 1,4-naphthoquinone. There are relatively few studies on 1,4-naphthoquinone without any substituents at the 5 and 8 positions

Method used

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  • 2-octyl sulfoxide-1,4-naphthoquinone compound
  • 2-octyl sulfoxide-1,4-naphthoquinone compound
  • 2-octyl sulfoxide-1,4-naphthoquinone compound

Examples

Experimental program
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Embodiment

[0025] Example: Preparation of 2-octylsulfoxide-1,4-naphthoquinone

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

[0027] In a 100ml reaction bottle, add 158.15mg (1mmol) of 1,4-naphthoquinone and 30ml of methanol, mix well, add 266.6μl (1.5mmol) of 1-octylthiol, react at room temperature for 4 hours, then add heavy Sodium chromate 59.6mg (0.2mmol) and concentrated sulfuric acid 40.8μl (0.75mmol), the reaction ends 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-octylmercapto-1,4-naphthoquinone.

[0028] (2) Synthesis of 2-octylsulfoxide-1,4-naphthoquinone (OSNQ)

[0029] In a 50ml reaction bottle, add 302.43mg (1mmol) of the above product 2-octylmercapto-1,4-naphthoquinone and 20ml of chloroform, slowly add 276.1mg (1.2mmol) of 3-chloroperoxybenzoic acid (MCPBA), 0 React ...

experiment example

[0031] 1. The killing effect of OSNQ 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, 20, 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 wa...

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PUM

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Abstract

The invention discloses a 2-octyl sulfoxide-1,4-naphthoquinone compound which solves the problem that the research on 1,4-naphthoquinone without any substituent groups at the fifth bit and the eighth bit is little. The structural formula of the compound can be seen in the description. No substituent groups are arranged at the fifth bit or the eighth bit of the compound, the second bit is substituted by sulfydryl, sulfur at the second bit is oxidized into sulfoxide, and the naphthoquinone compound can have more excellent anti-cancer activity.

Description

technical field [0001] The present invention relates to a novel compound. 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 protein tyrosine kinase, and resist angiogenesis. Therefore, naphthoquinones have always been a class of compounds of interest to many researchers. [0003] In recent years, the research on naphthoq...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/24C07C315/02
CPCC07C315/02C07C317/24C07C319/18C07C321/28
Inventor 金成浩臧延青罗英花孙虎男申贵男刘畅蒋雪园吴丹丹孟令旗王浩徐婉婷
Owner HEILONGJIANG BAYI AGRICULTURAL UNIVERSITY
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