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Tabersonine derivative, pharmaceutical compositions, preparing method and medical application thereof

A technology of glycyrrhizin and compound, applied in the field of application in the preparation of medicines for treating or preventing cancer

Active Publication Date: 2012-07-11
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no previous report on the medicinal activity of this compound

Method used

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  • Tabersonine derivative, pharmaceutical compositions, preparing method and medical application thereof
  • Tabersonine derivative, pharmaceutical compositions, preparing method and medical application thereof
  • Tabersonine derivative, pharmaceutical compositions, preparing method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Preparation of methoxyglycyrrhizine and acetonylglycyrrhizine:

[0114] Glycyrrhizine hydrochloride, peroxybenzoic anhydride, NBS and 5eq methanol were dissolved in CCl4, and refluxed for 5h under anhydrous and anaerobic conditions to obtain glycyrrhizine hydrochloride methoxy derivatives, and then methoxy derivatives, trifluoromethanesulfonic acid Dissolve silver and methyl ketone in acetonitrile and react at room temperature for 10 hours to obtain acetone derivatives. ESI: 393[M+1] + , 1 H-NMR (CDCl3, 500MHz) δ: 7.34 (m, H-12), 7.13 (m, H-10), 7.02 (t, H-11), 6.86 (dd, H-9), 5.86 (m, H-14), 5.72(m, H-15), 4.04(m, H-3), 3.68(-OCH3), 3.30(d, -CH2-), 3.01-2.78(m, H-5), 2.61 (s, H-21), 2.58-2.04 (dddd, H-17), 2.16 (COCH3), 2.01 (m, H-6), 0.91 (m, H-19), 0.67 (m, H-18) .

[0115]

Embodiment 2

[0117] Alternative method for preparing acetonyl hydroglycyrrhizine:

[0118] Dissolve AIBN, NBS, 5eq acetone, and potassium carbonate or cesium carbonate as base in dichloromethane, and reflux under anhydrous and oxygen-free conditions to obtain the target compound. ESI: 393[M+1] + .

[0119] (1)

[0120]

Embodiment 3

[0122] Preparation of bromoglycyrrhizine and conversion to acetonylglycyrrhizine:

[0123] Glycyrrhizine, NBS, peroxybenzoic anhydride, in CCl 4 Reflux overnight to obtain brominated derivatives, and then catalyzed by trifluoroacetic acid, silver trifluoromethanesulfonate as base, brominated derivatives and acetone were dissolved in dichloromethane to obtain the target compound. Bromo derivatives: ESI: 415[M+1] + . Acetone derivatives: ESI: 393[M+1] + .

[0124]

[0125] The following derivatives of hydroglycyrrhizine can be prepared according to a similar method:

[0126] Acetophenonyl glycyrrhizine:

[0127]

[0128] Ethynyl hydroglycyrrhizine:

[0129]

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PUM

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Abstract

The invention provides antineoplastic active ingredient tabersonine derivative, as is shown in formula (I), pharmaceutical compositions, and the preparing method and the medical application thereof.

Description

Technical field: [0001] The present invention belongs to the technical field of medicines, in particular, it relates to monoterpene indole alkaloid compound water licorice (tabersonine) derivatives and their organic and inorganic acid salts with a novel skeleton, and a pharmaceutical composition using it as the active ingredient of the medicine. Preparation methods and their application in the preparation of medicines for treating or preventing cancer. Background technique: [0002] Tumor is a worldwide problem. In China, 1.6 million new cancer patients are added every year, and 1.3 million cancer patients die every year. Although the currently used chemotherapeutic drugs have a certain curative effect, they bring great physical pain and mental stress to the patients due to their high toxicity. The discovery of new anti-tumor drugs with definite curative effect and relatively less toxic and side effects is imminent. Tabersonine derivatives are chemically synthesized deriva...

Claims

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Application Information

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IPC IPC(8): C07D471/20C07D519/04A61K31/437A61P35/00A61P35/02
Inventor 罗晓东蔡祥海刘亚平李艳夏成峰石洪凯
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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