A kind of polysubstituted naphthoquinone derivatives and its preparation method and application

A derivative and multi-substituted technology, applied in the field of multi-substituted naphthoquinone derivatives and their preparation, can solve problems such as large toxic and side effects, and achieve the effects of low cost, good inhibitory effect and novel structure

Active Publication Date: 2022-06-28
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the skeleton structure of 1,4-naphthoquinone is widely distributed, and juglone, lapaquinone, vitamin K3 and lancidone extended from this type of natural naphthoquinone have shown good antitumor activity, but some natural naphthoquinones Classes (such as lapaquinone) limit its clinical application due to its large toxic and side effects

Method used

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  • A kind of polysubstituted naphthoquinone derivatives and its preparation method and application
  • A kind of polysubstituted naphthoquinone derivatives and its preparation method and application
  • A kind of polysubstituted naphthoquinone derivatives and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The preparation of embodiment 1 many substituted naphthoquinone derivatives

[0041] The preparation method of many substituted naphthoquinone derivatives is carried out according to the following reaction formula:

[0042]

[0043] In the formula, R 1 Is ethoxy, diphenylmethoxy, Maolin alcohol, D-menthol, etc.; R 2 For thiophene, phenyl, p-bromophenyl, p-methoxyphenyl, 2,4,6-trimethylphenyl, etc.; R 3 For hydrogen, nitro, etc.; R 4 For hydrogen, fluorine, bromine, etc.

[0044]The preparation method of many substituted naphthoquinone derivatives is specifically: the diazo compound (0.20mmol) shown in formula SI-1 in the above-mentioned reaction formula, the benzisoxazole (0.24mmol) shown in formula SI-2 and catalyst ( Acetonitrile) [(2-biphenyl) di-tert-butylphosphine] gold (I) hexafluoroantimonate (0.01mmol) was weighed in a test tube, and then 2 mL of anhydrous 1,2-dichloroethane was added to the reaction system, The reaction was stirred at 30° C. for 24 hour...

Embodiment 2

[0059] Example 2 Inhibitory activity of multi-substituted naphthoquinone derivatives on colorectal adenocarcinoma cells

[0060] 1. The human colorectal adenocarcinoma cells used in the determination are: colorectal adenocarcinoma cells (HCT-116) (purchased from Guangzhou Saiku Biotechnology Co., Ltd.);

[0061] 2. Using the CCK-8 method to measure the inhibitory effect of polysubstituted naphthoquinone derivatives on the proliferation of human colorectal adenocarcinoma cells, wherein the specific determination process of the inhibitory rate of HCT-116 cells is as follows:

[0062] 1) Add 100 μL of cell suspension prepared with complete medium to the 96-well plate (5000 cells / well), and add 100 μL of cell culture solution without cells to the blank well as a control, and inoculate the well The 96-well culture plate was pre-incubated for 24 hours in an incubator (37°C, 5% CO 2 );

[0063] 2) Add 1.0 μL of a solution of the compounds to be tested (compounds I-1 to I-10) dissol...

Embodiment 3

[0079] Example 3 Inhibitory activity of multi-substituted naphthoquinone derivatives on osteosarcoma cells

[0080] 1. The human osteosarcoma cells used in the determination are: human osteosarcoma cells (SJSA-1) (purchased from Guangzhou Saiku Biotechnology Co., Ltd.);

[0081] 2. The inhibitory effect of multi-substituted naphthoquinone derivatives on human osteosarcoma cell proliferation was determined by CCK-8 method, wherein the specific determination process of the inhibition rate of SJSA-1 cells was as follows:

[0082] 1) Add 100 μL of cell suspension prepared with complete medium to the 96-well plate (5000 cells / well for inoculation), and add 100 μL of cell culture solution without cells to the blank well as a control, and inoculate the well The 96-well culture plate was pre-incubated for 24 hours in an incubator (37°C, 5% CO 2 );

[0083] 2) Add 1.0 μL of a solution of the compounds to be tested (compounds I-1 to I-10) dissolved in DMSO to the culture plate so that...

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Abstract

The invention belongs to the technical field of medicinal chemistry, and specifically relates to a multi-substituted naphthoquinone derivative and its preparation method and application. The structure of the derivative is shown in the general formula (I), wherein, R 1 selected from ethoxy, diphenylmethoxy, linalyl, D-menthol; R 2 selected from thiophene, phenyl, p-bromophenyl, p-methoxyphenyl, 2,4,6-trimethylphenyl; R 3 selected from hydrogen, nitro; R 4 Selected from hydrogen, fluorine, and bromine; the derivative has a novel structure and has a good antitumor effect, especially has a good inhibitory effect on colorectal adenocarcinoma cells, osteosarcoma cells and breast cancer cells. It has great application value and is expected to be prepared as an antitumor drug; at the same time, the preparation method of the polysubstituted naphthoquinone derivative has fewer reaction steps, simple and safe operation, low cost, less waste generation, high atom economy, and high selectivity. Sex, the advantage of high yield.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to a multi-substituted naphthoquinone derivative and its preparation method and application. Background technique [0002] Malignant tumors are one of the diseases that pose a great threat to human health. According to relevant statistics from the China Cancer Management Center, the incidence and death of malignant tumors in China have shown an upward trend in recent years. According to the 2018 global cancer statistics report of the official journal of the American Cancer Society "Journal of Cancer for Clinicians", the cancers with the largest number of new cases and deaths are lung cancer, breast cancer, prostate cancer, colon cancer, non-melanoma of the skin, gastric cancer, Liver cancer, rectal cancer, etc. Clinically, drug therapy is still the main treatment for tumors. However, the anti-tumor drugs currently used in clinical practice are far from meeti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/24C07C251/22C07C249/02A61K31/216A61K31/381A61P35/00
CPCC07D333/24C07C251/22A61P35/00C07C2601/14C07C2602/26
Inventor 徐新芳谢雄达鲍明黄晶晶张芷菁史滔达胡文浩
Owner SUN YAT SEN UNIV
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