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Ursdic acid isatin amide derivatives as well as preparation method and application thereof

A technology of indole quinone amide and ursolic acid, which is applied in the direction of drug combination, steroids, anti-tumor drugs, etc., can solve the problem of lack of anti-tumor activity and achieve the effect of novel structure

Active Publication Date: 2020-02-07
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

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

Method used

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  • Ursdic acid isatin amide derivatives as well as preparation method and application thereof
  • Ursdic acid isatin amide derivatives as well as preparation method and application thereof
  • Ursdic acid isatin amide derivatives as well as preparation method and application thereof

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preparation example Construction

[0043] The preparation method of the ursolic acid indole quinone amide derivative I-a to I-i of structure shown in general formula (I) of the present invention comprises the steps:

[0044] (1) ursolic acid obtains 3-oxidized ursolic acid through Jones reagent oxidation reaction, has the structure shown in general formula II:

[0045]

[0046] (2) 3-oxidized ursolic acid and 3,5-dimethoxyphenylhydrazine are synthesized by Fishier indole to obtain 3,5-dimethoxyindole derivatives, which have the structure shown in the general formula III:

[0047]

[0048] (3) Vilsmeier-Haack formylation of indole derivatives with phosphorus oxychloride and N,N-dimethylformamide to obtain 3,5-dimethoxy-2-formyl indole derivatives, Has the structure shown in general formula IV:

[0049]

[0050] (4) compound IV is carried out oxidation reaction with hydrogen peroxide, obtains ursolic acid indole quinone derivative, has the structure shown in general formula V:

[0051] (5) Compound V...

Embodiment 13

[0067] The synthesis of embodiment 13-oxidized ursolic acid (II) of the present invention

[0068]Add 2g (4.6mmol) of ursolic acid and 250mL of acetone into a 500mL round bottom flask, stir to dissolve, 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 Virahol stirring reaction 30min, after reaction finishes, filter and precipitate and collect filtrate, the light yellow-green viscous solid that filtrate concentrating under reduced pressure obtains is 3-oxidized ursolic acid (II) ( 1.2 g, 65.6%).

Embodiment 2

[0070] Synthesis of 3,5-Dimethoxindole Derivative of Ursolic Acid (III)

[0071] Weigh 0.33 g (3 mmol) of 3,5-dimethoxyaniline and dissolve it in 3 mL of 20% hydrochloric acid in a single-necked round bottom flask. Then weigh 0.28 g (4 mmol) of sodium nitrite and dissolve it in 0.7 mL of water, slowly drop it into the reaction flask under ice-bath conditions, and stir and react under ice-bath conditions for 1 h. Weigh 1.35g (6mmol) of tin protochloride and dissolve it in 1.8mL of concentrated hydrochloric acid, slowly drop it into the flask where the previous step reaction under ice-bath conditions is completed, stir at room temperature for 2 hours, carry out suction filtration after the reaction is completed, and the solid is 3,5-Dimethoxyphenylhydrazine.

[0072] Weigh 0.441g (1mmol) of 3-oxidized ursolic acid and dissolve it in 10mL of absolute ethanol, add 3,5-dimethoxyphenylhydrazine (3mmol) from the previous step into the system, and then add 0.5mL of concentrated hydro...

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Abstract

The invention discloses ursdic acid isatin amide derivatives as well as a preparation method and application thereof. The invention discloses ursdic acid isatin amide derivatives I-a to I-I with structures as shown in a general formula (I) and pharmaceutically acceptable salts thereof. The ursdic acid isatin amide derivatives and the pharmaceutically acceptable salts thereof disclosed by the invention have remarkable antitumor activity, and proven by pharmacological experiments, the ursdic acid isatin amide derivatives disclosed by the invention have an obvious effect on inhibiting human hepatoma cells HepG2 and SMMC-7721 and have the potential of developing antitumor drugs.

Description

technical field [0001] The invention relates to the technical fields of organic synthesis and medicinal chemistry, in particular to a class of ursolic acid indole quinone amide derivatives 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61P35/00
CPCC07J71/0047A61P35/00
Inventor 谷文马长悦王文燕陈浩李阿良王石发
Owner NANJING FORESTRY UNIV
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