Banisterine derivative compound and uses thereof

A technology of dehydrohalamine and compounds, applied in the field of pharmaceutical compounds, can solve the problems of no clinical development and application, low anti-tumor activity, etc.

Active Publication Date: 2008-03-12
XINJIANG HUASHIDAN PHARMA RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the antitumor activity of the dehydrohalamine derivatives disclosed so far is low (it has been reported in the literature that the highest tumor inhibition rate of dehydrohalamine derivatives to the tumor-bearing mouse test model is 46.9%), and there is no clinical evidence. The value of developing applications

Method used

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  • Banisterine derivative compound and uses thereof
  • Banisterine derivative compound and uses thereof
  • Banisterine derivative compound and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1: Synthesis of 9-phenylpropyl-β-carboline (2)

[0075] Mix N,N-dimethylformamide (100ml), 1-bromo-3-phenylpropane (15mmol) and potassium iodide (15mmol), heat and stir in a water bath at 60°C for 3h, then cool the reaction solution to room temperature and add sodium hydride (1.2g, 30mmol) and β-carboline 1 (1.68g, 10mmol), the reaction was stirred at room temperature, followed by TLC detection. After the reaction was completed, the reaction mixture was poured into ice water, extracted with ethyl acetate, the organic phase was washed with water and saturated brine; then the organic phase was acidified with concentrated hydrochloric acid, and concentrated to dryness under reduced pressure. Anhydrous ethanol was taken with water several times, and the residue was used Acetone was recrystallized to obtain white crystals. Dissolve the white crystals in water, basify with sodium bicarbonate, extract with ethyl acetate, wash the organic phase with water, wash with saturat...

Embodiment 2

[0076] Example 2: General synthesis process of 2-substituted 9-phenylpropyl-β-carboline alkaloid derivatives (3-6)

[0077] 9-Phenylpropyl-β-carboline 2 (5mmol), add 75ml ethyl acetate to completely dissolve it, add the corresponding bromine or iodoalkane (10mmol), heat to reflux for 8 hours, cool to room temperature, filter the precipitated solid After washing with ethyl acetate, the solid was dissolved in 50ml of absolute ethanol, heated to reflux until clarified, filtered while hot, placed in the refrigerator to recrystallize, filtered, and washed with absolute ethanol to obtain the product.

[0078] Embodiments 3-6 are all operated according to the above operation steps:

Embodiment 32

[0079] Example 32, 9-diphenylpropyl-β-carboline bromide (3): yellow crystals were obtained, m.p. 120-121°C.

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Abstract

The present invention relates to a harmine derivative compound and the application. The compound is produced through the structural modification of the 1st, 2nd, 3rd, 7th and 9th pint of the parent nuclear of the beta-carboline of the harmine; thus the novel harmine derivative compound is synthesized with the enhanced anti-tumor activity and no toxicity of the nervous system. Through the screening research of the vitro and vivo anti-tumor model, the harmine derivative compound is found to have the significant anti-tumor activity (the tumor-inhibition rate of the tumor-bearing mice model reaches as high as 63.5 percent), have no neurotoxicity, and have the prospects of clinical application. The preparation method of the compound is simple; the collection rate is high; and the compound is used for the drugs of treating various tumor diseases.

Description

Technical field [0001] The present invention relates to pharmaceutical compounds, especially alkaloid compounds, and more specifically to harmine derivatives of general formula (I) and applications thereof. Background technique [0002] Harmaine was first isolated from the seeds of the plant Pegannum harmala L. by Gobel in 1841. Subsequently, harmine was isolated from a variety of plants. Because the chemical structure of harmine contains a tricyclic β-carboline structure, it was later classified as β-carboline alkaloids with other compounds containing the same structure as β-carboline. [0003] Harmaine and its analogs are widely distributed in nature. Since the first isolation of harmine compounds, various harmine analogues have been isolated from marine organisms, plants, and mammalian body fluids and tissues. [0004] Harmaine and its analogues have a wide range of pharmacological effects, but there are two main aspects: nerve activity and anti-tumor activity. Before the 1980...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61P35/00
Inventor 武嘉林曹日晖于富生王子厚彭文烈
Owner XINJIANG HUASHIDAN PHARMA RES
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