Application of theanine nitrate aromatic amide in preparation of products for preventing and treating such diseases as cancer

A technology of nitric acid amide and theanine, which is applied in the medical field, can solve the problems of limited prevention and treatment, toxic and side effects, etc., and achieve the effects of enhancing curative effect, reducing toxic and side effects, and reducing toxic and side effects

Inactive Publication Date: 2014-06-11
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the toxic and side effects of clinical chemotherapy and rad

Method used

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  • Application of theanine nitrate aromatic amide in preparation of products for preventing and treating such diseases as cancer
  • Application of theanine nitrate aromatic amide in preparation of products for preventing and treating such diseases as cancer
  • Application of theanine nitrate aromatic amide in preparation of products for preventing and treating such diseases as cancer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A compound for treating tumors in this embodiment, its name is (R)-ethyl ester-2-(6-NO2-O-2H-benzopyran-3-carboxy)-5-(ethylamino)-5 -Oxopentanoate, referred to as theanine nitrosylamide (TNC), has the chemical structural formula shown in formula (I):

[0039] As the compound shown in formula (I), the physical properties are light yellow powdery solid, and the fusing point decomposes above 300 ° C;

[0040] The compound shown in formula (I) is a pharmaceutically acceptable carrier; the pharmaceutically acceptable carrier includes any substance suitable for injection, preferably water for injection, or emulsifier, liposome, nano preparation and other pharmaceutical carriers.

[0041] The preparation method of compound theanine nitrosylamide as shown in formula (I), mainly comprises the following steps:

[0042] 1, the preparation of intermediate 6-nitrocoumarin-3-carboxylic acid, as shown in structural formula (II);

[0043] 2, the preparation of intermediate ethyl the...

Embodiment 2

[0053] The difference between this embodiment and embodiment 1 is that

[0054] Step 1: Preparation of 6-nitro-coumarin-3-carboxylic acid

[0055] Dissolve 55 g of coumarin-3-carboxylic acid in 270 mL of concentrated sulfuric acid, cool to -10°C, add a mixed acid solution of concentrated nitric acid and concentrated sulfuric acid (90mL, the volume ratio of concentrated nitric acid and concentrated sulfuric acid is 1:3), at 0°C The reaction was stirred at lower temperature for 1.5 hours, and then raised to room temperature and stirred for 1.5 hours. The reaction solution was poured into 5500mL of ice water, left to stand for crystallization, suction filtered, washed with ice water, and dried to obtain a light yellow amorphous solid of 6-nitrocoumarin-3-carboxylic acid obtained as structural formula (II) 6- Nocoumarol-3-carboxylic acid.

[0056] Step 2: Preparation of ethyl theanine

[0057] Theanine is dissolved in ethanol at a ratio of 88g / L (referring to dissolving 88g of ...

Embodiment 3

[0061] The difference between this embodiment and embodiment 2 is that

[0062] Step 1: Preparation of 6-nitro-coumarin-3-carboxylic acid

[0063] Dissolve 60 g of coumarin-3-carboxylic acid in 300 mL of concentrated sulfuric acid, cool to -10 °C, add a mixed acid solution of concentrated nitric acid and concentrated sulfuric acid (100 mL, the volume ratio of concentrated nitric acid and concentrated sulfuric acid is 1:3), and The reaction was stirred at lower temperature for 2 hours, and then raised to room temperature and stirred for 2 hours. The reaction solution was poured into 6000mL of ice water, left to stand for crystallization, suction filtered, washed with ice water, and dried to obtain a light yellow amorphous solid of 6-nitrocoumarin-3-carboxylic acid obtained as structural formula (II) 6- Nocoumarol-3-carboxylic acid.

[0064] Step 2: Preparation of ethyl theanine

[0065] Theanine is dissolved in ethanol at a ratio of 91g / L (referring to dissolving 91g of thea...

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Abstract

The invention relates to the technical field of medical treatment. Theanine nitrate aromatic amide is a newly synthetic compound, can inhibit the growth and invasion of such cancer cells as human lung cancer, breast cancer, liver cancer, gastric cancer, colon cancer, prostate cancer, pancreatic cancer, cervical cancer, lymphoma, leukemia and melanoma or the like, and can significantly inhibit tumor growth and metastasis in vivo, and the inhibitory effect of the theanine nitrate aromatic amide exceeds that of anticancer drugs; the action mechanism involves down-regulation of receptors closely related to inhibition of tumor growth, invasion and metastasis, regulation and control of protein and kinase levels and combination of a nuclear factor with DNA by signal transduction, and up-regulation of such factors as cancer suppressor protein and cell cycle inhibitory protein factor or the like; the theanine nitrate aromatic amide can directly inhibit the activity of histone deacetylase and histone methyltransferase EZH2 and the combination of an inflammatory factor NF-kappa B and DNA, and the activity of the nitrate fluorine aromatic amide exceeds that of the anticancer drugs. The invention provides a new use of the theanine nitrate aromatic amide in prevention and treatment of such diseases as tumor, inflammation, cardiovascular and cerebrovascular diseases and immunodeficiency, etc.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to the preparation of theanine nitrosylamide (TNC) and its intermediate compound 6-nitro-3-carboxylic acid coumarin (NC) and theanine ethyl ester (TE). And the application of disease inhibitors in the treatment of tumors, inflammation, cardiovascular and cerebrovascular diseases, and immunodeficiency. Background technique [0002] The abnormal growth, invasion and metastasis of malignant tumors such as human lung cancer, breast cancer, liver cancer, gastric cancer, colon cancer, prostate cancer, pancreatic cancer, cervical cancer and chronic leukemia, lymphoma and melanoma lead to the death of tens of thousands of patients every year It has become a major disease that seriously endangers human health. Due to the toxic and side effects of clinical chemotherapy and radiotherapy, the effective prevention and treatment of it is limited. Theanine (also known as glutamyl ethylamine) is...

Claims

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Application Information

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IPC IPC(8): A61K31/37A61K31/223A61P35/00A61P35/02A61P29/00A61P9/00A61P37/02
Inventor 张国营关玉昆刘昆张颖吴犇昊
Owner YANTAI UNIV
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