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A kind of ursolic acid indole quinone derivatives and preparation method and application thereof

A technology of aldehyde indole derivatives and dimethoxyindole derivatives, which is applied in the field of ursolic acid indole quinone derivatives and their preparation, can solve the problems of lack of anti-tumor activity and achieve novel structures Effect

Active Publication Date: 2021-10-12
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is a lack of a class of ursolic acid indole quinone derivatives with high anti-tumor activity and its preparation method and application

Method used

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  • A kind of ursolic acid indole quinone derivatives and preparation method and application thereof
  • A kind of ursolic acid indole quinone derivatives and preparation method and application thereof
  • A kind of ursolic acid indole quinone derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1 (1) synthetic 3-oxidized ursolic acid (II):

[0034] Add 4.6mmol of ursolic acid and 250mL of acetone into a 500mL round bottom flask, stir to dissolve, then stir in ice water for 15min, slowly add 1.87mL of Jones reagent dropwise and rise to room temperature, stir for 5h, then add 90mL of isopropanol Stirring and reacting for 30min, after the reaction was finished, the precipitate was filtered to collect the filtrate, the light yellow-green viscous solid obtained by concentrating the filtrate under reduced pressure was recrystallized with methanol, and the white needle-like crystal obtained was 3-oxyursolic acid (II) (1.2g, 65.6%).

[0035]

[0036] (2) Synthesis of ursolic acid 3,5-dimethoxindole derivative (III):

[0037] Weigh 3mmol of 3,5-dimethoxyaniline and dissolve it in 3mL of 20% hydrochloric acid in a single-necked round bottom flask. Then weigh 4 mmol of sodium nitrite and dissolve it in 0.7 mL of water, slowly drop it into the reaction fla...

Embodiment 2

[0050] Synthesis of indolequinone ursolic acid ester (I-b):

[0051] Dissolve 0.054 g of compound V in Example 1 in benzene, slowly drop 50 μL of SOCl 2 Afterwards, the temperature was gradually raised to 80°C, and the reaction was refluxed for 4 hours. When the wetted pH test paper is placed in the exhaust port, the test paper does not turn red, indicating that the reaction is over, concentrate under reduced pressure, and remove the benzene and SOCl in the reaction solution. 2 After steaming, ursolic acid indole quinone acid chloride was obtained in the form of yellow oil. Dissolve ursolic acid indoloquinone chloride with 6 mL of diethyl ether and slowly add 0.225 mmol of ethanol and 30 μL of triethylamine in dichloromethane dropwise under ice-bath conditions, slowly rise to room temperature and stir for 6 h. After the reaction, the reaction solution was poured into a mixture of ice and water, and extracted three times with dichloromethane after the ice melted; the combined...

Embodiment 3

[0054] Synthesis of indolequinone ursolic acid ester (I-c):

[0055]Dissolve 0.054 g of compound V in Example 1 in benzene, slowly drop 50 μL of SOCl 2 Afterwards, the temperature was gradually raised to 80°C, and the reaction was refluxed for 4 hours. When the wetted pH test paper is placed in the exhaust port, the test paper does not turn red, indicating that the reaction is over, concentrate under reduced pressure, and remove the benzene and SOCl in the reaction solution. 2 After steaming, ursolic acid indole quinone acid chloride was obtained in the form of yellow oil. Dissolve ursolic acid indoloquinone chloride with 6 mL of ether and slowly add 0.225 mmol of isopropanol and 30 μL of triethylamine in methylene chloride solution dropwise under ice-bath conditions, slowly rise to room temperature and stir for 6 h. After the reaction, the reaction solution was poured into a mixture of ice and water, and extracted three times with dichloromethane after the ice melted; the c...

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Abstract

The invention discloses an indole quinone derivative of ursolic acid, a preparation method and application thereof, and belongs to the technical fields of organic synthesis and medicinal chemistry. The general structural formula of this ursolic acid indole quinone base derivative is shown in formula (I): the ursolic acid indole quinone base derivative of the present invention has significant antitumor activity, and pharmacological experiments show that it has Cervical cancer cell line HeLa, breast cancer cell line MCF‑7 and liver cancer cell line HepG2 have significant inhibitory effects, and have the potential to develop anti-tumor drugs.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and medicinal chemistry, and in particular relates to a ursolic acid indole quinone derivative and a preparation method and application thereof. Background technique [0002] Malignant tumors are diseases that seriously threaten human health and social development. According to the latest statistics of the World Health Organization, 8.8 million people die of cancer every year in the world, accounting for about 1 / 6 of the total number of deaths in the world every year, and the incidence of malignant tumors in China accounts for about 21.8% of the world. The main means of tumor treatment include surgical treatment, radiotherapy (abbreviated as radiotherapy), chemical drug therapy (abbreviated as chemotherapy) and cellular immunotherapy. Among them, chemotherapy, as a routine treatment method, uses cytotoxic drugs such as DNA synthesis inhibitors or cell division inhibitors to inhibit tumo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61P35/00
CPCA61P35/00C07J71/0047
Inventor 谷文王文燕李阿良王石发刘青松孙月
Owner NANJING FORESTRY UNIV
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