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Indole carbazole and bisindole maleimide alkaloid, preparation method and application thereof

A derivative, diindole technology, applied in the application field of tumor treatment, can solve the problems of poor curative effect, large toxic and side effects, etc.

Active Publication Date: 2010-08-25
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional cytotoxic drugs often have problems such as poor curative effect, large toxic and side effects, and easy drug resistance, which limit their clinical use

Method used

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  • Indole carbazole and bisindole maleimide alkaloid, preparation method and application thereof
  • Indole carbazole and bisindole maleimide alkaloid, preparation method and application thereof
  • Indole carbazole and bisindole maleimide alkaloid, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] [Example 1] Preparation of Compounds 1-10

[0018] Preparation of Compound 1

[0019] i) Preparation of 2-(1-ethyl-1H-indol-3-yl) acetic acid (1a)

[0020]Under the protection of argon, in a 250mL three-necked flask, add sodium hydride (4g, 100mmol, 60% dispersed in paraffin), add 80mL tetrahydrofuran and stir to suspend at 0°C, add 30mL tetrahydrofuran dissolved indole-3-acetic acid (3.5 g, 20mmol), after stirring for half an hour, add 30mL tetrahydrofuran dissolved ethyl iodide (5mL, 60mmol) dropwise, slowly rise to room temperature, after reacting overnight, drop down to 0°C, add dropwise 10 drops of methanol, and then add appropriate amount of water To obtain a bright yellow solution, extract with ethyl acetate, add concentrated hydrochloric acid to the aqueous layer and extract again, combine the organic layers, and wash with anhydrous Na 2 SO 4 Dry, evaporate to dryness in vacuo, and separate through silica gel column (petroleum ether: ethyl acetate 8:1) to obt...

Embodiment 2

[0083] [Example 2] Test of antitumor activity

[0084] 1 Cytotoxic activity

[0085] 1.1 Test method

[0086] Preparation of the test sample solution: the test samples are the monomer compounds 1-10 synthesized in the above-mentioned Example 1. Accurately weigh an appropriate amount of sample and prepare a solution with the required concentration with DMSO for activity testing.

[0087] Cell lines and subculture of cells: A549, BEL-7402 and HL-60 cell lines were used for activity testing. All kinds of cells were subcultured in RPMI-1640 medium containing 10% FBS in an incubator with 5% carbon dioxide at 37°C.

[0088] Cell Proliferation Inhibitory Activity Test Method

[0089] The invention adopts the MTT method to test and evaluate the inhibitory activity of the tested sample on the proliferation of HL-60 cancer cells. The dehydrogenase in the mitochondria of living cells can metabolize and reduce the yellow 3-(4,5-dimethylthiazole)-2,5-diphenyltetrazolium bromide to blu...

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Abstract

The invention relates to indole carbazole and bisindole maleimide alkaloid, a preparation method and application thereof. In the preparation method, the compound of the type with a novel structure is prepared by a chemical reaction starting from indole and indoleacetic acid. An experiment confirms that the compound has tumor cytotoxin activeness and protein kinase C(PKC) inhibitory activity, so the compound can be used as an cell proliferation inhibitor or an antitumor agent.

Description

Technical field: [0001] The invention relates to an indolecarbazole and bisindolemaleimide alkaloids with protein kinase C (PKC) inhibitory activity and anti-tumor effect. The invention discloses its preparation method and its application in tumor treatment. application. Background technique: [0002] Malignant tumor is a major disease that endangers human life and health, and its incidence is on the rise every year. Traditional cytotoxic drugs often have problems such as poor curative effect, high toxicity and side effects, and easy drug resistance, which limit their clinical use. In recent years, the development of molecularly targeted drugs targeting cell receptors, key genes, and regulatory molecules, especially drugs that combine multiple targets to block cell signal transduction, has become a new development direction for anti-tumor drugs. Studies have shown that protein kinase C (Protein Kinase C, PKC) is highly expressed in a variety of tumor cells, plays an import...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07D403/14C07D487/14A61P35/00A61K31/404A61K31/407A61K31/7056
Inventor 朱伟明徐志红张亚鹏王乂刘培培
Owner OCEAN UNIV OF CHINA
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