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Anti-tumor natural medicine coupled with nitric oxide donor and medical use thereof

A technology of nitric oxide and natural medicine, applied in the field of medicine for diseases, can solve problems such as insufficient effect

Inactive Publication Date: 2011-04-06
CHIFCON DRUG DISCOVERY SUZHOU
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the current natural anti-tumor drugs are not strong enough, which limits their further application.

Method used

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  • Anti-tumor natural medicine coupled with nitric oxide donor and medical use thereof
  • Anti-tumor natural medicine coupled with nitric oxide donor and medical use thereof
  • Anti-tumor natural medicine coupled with nitric oxide donor and medical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1: Rhein and Nitric Oxide Donor Coupling Compound I

[0091] The synthetic equation of this coupling compound I is:

[0092]

[0093] The chemical name of this coupling compound I:

[0094] 4-(2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbonyloxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide.

[0095] The preparation process of this coupling compound I is:

[0096] The first step: slowly add NaOH (70mmol) with a mass ratio of 50% to compound 2 (chemical name: 3,4-bis(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide, 70mmol) and bromine Ethanol (70mmol) in THF (400ml) solution, the resulting mixture was stirred at room temperature for 16 hours, then 50% NaOH (20mmol) was added dropwise and stirred for 2 hours to complete the reaction. The organic solvent was evaporated and the remaining material was poured into ice water. The product was repeatedly extracted three times with dichloromethane (100 ml), the organic layers were combined, dried over an...

Embodiment 2

[0101] Example 2: Rhein and Nitric Oxide Donor Coupling Compound II

[0102] The synthetic equation of this coupling compound II is:

[0103]

[0104] The chemical name of the coupling compound II:

[0105] (Z)-2-((4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbonyloxy)methoxy)-1-(pyrrolidin-1-yl)diazene oxide.

[0106] The preparation process of this coupling compound II is:

[0107] Compound 1 (rhein, 14mmol) was dissolved in DMF (100ml), and Na 2 CO 3 (15mmol) and KI (2mmol), after stirring for 15 minutes, add compound 4 (chemical name: (Z)-2-(chloromethoxy)-1-(pyrrolidin-1-yl) diazene oxide, 12mmol). The resulting compound was stirred at 100°C for 16 hours. After cooling, the solid was filtered off, the product was extracted three times with EtOAc (30ml), the organic layers were combined, dried over anhydrous magnesium sulfate, filtered and the solvent was evaporated. Compound II (0.8 g) was purified by silica gel chromatography (Haxane-20% haxane / EtOAc).

...

Embodiment 3

[0113] Example Three: Ursolic Acid and Nitric Oxide Donor Coupling Compound III

[0114] The chemical structure of this coupling compound III is:

[0115]

[0116] The chemical name of this coupling compound III:

[0117] (Z)-2-(((1S, 2R, 6aS, 6bR, 10S, 12aR, 12bR)-10-hydroxy-1, 2, 6a, 6b, 9, 9, 12a-heptamethyl-1, 2, 3, 4, 4a, 5, 6, 6a, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 12b, 13, 14b-icosahydropicene-4a-carbonyloxy)methoxy)-1-(pyrrolidin-1- yl) diazene oxide.

[0118] The preparation process of the coupling compound III is the same as that of Example 2, only the natural ingredients have been changed, so it will not be repeated. The prepared coupling compound III (2.0 g) was proved by means of nuclear magnetic resonance, mass spectrometry and elemental analysis, and the coupling compound III did have the elemental composition and molecular structure described in the above molecular formula. The specific parameters are:

[0119] 300mz 1 H NMR (DMSO-d6) δ5.74(s, 2H), 5.24...

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Abstract

The invention relates to an anti-tumor natural medicine coupled with a nitric oxide donor and medical use thereof. The medicine has a chemical structure shown in the general formula (I), which couples an anti-tumor natural medicine and a nitric oxide donor and can be used for preparing a medicament for preventing and curing tumor and cancer diseases. After entering a human body, the medicament can release nitric oxide and the components of the natural medicine at the disease symptom points in vivo, double suppression effects on the tumor or cancer lesion cells can be realized, and the toxic or side effect of the natural medicine is avoided.

Description

technical field [0001] The invention relates to a class of antitumor drugs and their medical applications, in particular to a class of drugs capable of enzymatically releasing nitric oxide free radicals in vivo, having anti-tumor dual effects, and can be used to prepare drugs for treating diseases such as tumors and cancers. Background technique [0002] Nitric oxide (hereinafter abbreviated as NO), as a free radical gas, is a low molecular weight and hydrophobic bioactive molecule in the human body, which can freely pass through the cell membrane and act on target molecules in the cell. In theory, nitric oxide can reach any part of cells and tissues, and can regulate various cell functions and produce a wide range of biological effects in vivo. Therefore, nitric oxide donors and regulators have important application value in the research and development of new drugs. [0003] As a biological effect molecule, NO participates in various important physiological effects in the ...

Claims

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Application Information

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IPC IPC(8): A61K31/4245A61K31/40A61K31/58A61P35/00
CPCA61K47/48023A61K31/56A61K31/19A61K31/58A61K47/54A61P35/00
Inventor 冯子侠刘晓东
Owner CHIFCON DRUG DISCOVERY SUZHOU
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