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9-hydroxyphenanthrenequinone derivative as well as preparation method and application thereof

A technology for hydroxyphenanthrenequinone and derivatives, which is applied in the field of 9-hydroxyphenanthrenequinone derivatives and their preparation, can solve the problems that antitumor drugs cannot meet the treatment requirements and lack effective tumor treatment, and achieves high atom economy and good antitumor performance. Effect, novel structure

Active Publication Date: 2021-04-09
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the anti-tumor drugs currently used in clinical practice are far from meeting the requirements of treatment, and there is still a lack of effective drugs for the treatment of tumors.

Method used

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  • 9-hydroxyphenanthrenequinone derivative as well as preparation method and application thereof
  • 9-hydroxyphenanthrenequinone derivative as well as preparation method and application thereof
  • 9-hydroxyphenanthrenequinone derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Preparation of 9-hydroxyphenanthrenequinone derivatives

[0045] The preparation method of 9-hydroxyphenanthrenequinone derivative is carried out according to the following reaction formula:

[0046]

[0047] In the formula, R 1 For hydrogen, bromine, etc.; R 2 For hydrogen, methyl, etc.; R 3 It is hydrogen, benzene, thiophene, furan, isobutyl, phenethyl, halogenated phenyl, methyl substituted phenyl, tert-butyl substituted phenyl, etc.

[0048] Homoacetylenic alcohol (0.60mmol) shown in formula 1 in the above reaction formula, phenanthrenequinone (0.4mmol) shown in formula 2, [2-(dicyclohexylphosphine)-3,6-dimethoxy-2' ,4',6'-triisopropyl-1,1'-diphenyl] bis(trifluoromethanesulfonimide) gold catalyst (0.02mmol), oxidizing agent (its structural formula is shown in O1, 0.60mmol) and trifluoromethanesulfonic acid (0.80mmol) were weighed in a test tube, then 10mL of anhydrous 1,2-dichloroethane was added to the reaction system, and the reaction was stirred at...

Embodiment 2

[0068] Example 2 Inhibitory activity of 9-hydroxyphenanthrenequinone derivatives on small cell lung cancer cells

[0069] 1. Human small cell lung cancer cells and tumor cells used in the determination are: human small cell lung cancer cells (H446) and human small cell lung cancer cells (H128).

[0070] 2. Using the CCK-8 method to determine the inhibitory effect of 9-hydroxyphenanthrenequinone derivatives on the proliferation of human small cell lung cancer cells, wherein the specific determination process of H446 cells and H128 cells is as follows:

[0071] (1) Make single-cell suspensions of H446 and H128 human small cell lung cancer cell lines respectively, take 100 μL and inoculate them in 96-well culture plates, the concentration of single-cell suspensions is 3000 cells / well, and then place in CO 2 in an incubator (37°C, 5% CO 2 , 95% air) overnight.

[0072] (2) Dissolve 9-hydroxyphenanthrenequinone derivatives (compounds I-1 to I-13) in DMSO respectively, prepare 10 ...

Embodiment 3

[0083] Example 3 Inhibitory activity of 9-hydroxyphenanthrenequinone derivatives on non-small cell lung cancer cells

[0084] 1. The human non-small cell lung cancer cell tumor cell used in the determination is: human non-small cell lung cancer cell (A549).

[0085] 2. The CCK-8 method was used to measure the inhibitory effect of 9-hydroxyphenanthrenequinone derivatives on the proliferation of human non-small cell lung cancer cells (A549). The specific measurement process was as follows:

[0086] (1) Make a single cell suspension of A549 human small cell lung cancer cell line, take 100 μL and inoculate it in a 96-well culture plate, the concentration of the single cell suspension is 6000 cells / well, and then place in CO 2 in an incubator (37°C, 5% CO 2 , 95% air) overnight culture;

[0087] (2) Dissolve 9-hydroxyphenanthrenequinone derivatives (compounds I-1 to I-13) in DMSO to prepare a 3.3mM stock solution, then dilute it with a blank medium to a concentration of 10μM, and...

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Abstract

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a 9-hydroxyphenanthrenequinone derivative as well as a preparation method and application of the 9-hydroxyphenanthrenequinone derivative; wherein R1 is hydrogen, bromine and the like; R2 is hydrogen, methyl or the like; R3 is hydrogen, benzene, thiophene, furan, isobutyl, phenethyl, halogenated phenyl, methyl substituted phenyl, tert-butyl substituted phenyl and the like. The derivative is novel in structure, has good anti-tumor activity, especially has a good inhibition effect on small cell lung cancer cells, non-small cell lung cancer cells and osteosarcoma cells, also has a certain inhibition effect on prostate cancer cells, and has great application potential in the aspect of anti-tumor effect. Meanwhile, the preparation method has the advantages of few reaction steps, simplicity and safety in operation, low cost, high atom economy, high selectivity and high yield.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to a 9-hydroxyphenanthrenequinone derivative and a preparation method and application thereof. 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 mee...

Claims

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Application Information

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IPC IPC(8): C07D307/32C07D307/46C07D409/04A61K31/341A61P35/00
CPCC07D307/32C07D307/46C07D409/04A61P35/00
Inventor 徐新芳鲍明黄晶晶洪科苗王军舰胡文浩
Owner SUN YAT SEN UNIV
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