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Application of ethyl coumarin-3-carboxylyl L-theanine and the like in preparation of product used for preventing and treating disease such as cancers

A technology of tea ethyl aromatic acid and ethyl theanine, applied in the medical field, can solve the problems of limited prevention and treatment, toxic and side effects, etc., and achieve the effect of enhancing curative effect, less toxic and side effects, and wide indications

Inactive Publication Date: 2014-04-02
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 radiotherapy, the effective prevention and treatment of it is limited

Method used

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  • Application of ethyl coumarin-3-carboxylyl L-theanine and the like in preparation of product used for preventing and treating disease such as cancers
  • Application of ethyl coumarin-3-carboxylyl L-theanine and the like in preparation of product used for preventing and treating disease such as cancers
  • Application of ethyl coumarin-3-carboxylyl L-theanine and the like in preparation of product used for preventing and treating disease such as cancers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A compound for treating tumors in this embodiment, its name is ethyl 5-ethylamino-5-oxo-2-(2-oxo-2H-benzopyran-3-carboxamido)pentanoate, Abbreviated as tea ethyl aromatic acid (TEC), it has the chemical structural formula shown in formula (I):

[0036] As the compound shown in formula (I), the physical properties are white powdery solid, and the melting point decomposes above 180 ° C;

[0037]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.

[0038] The preparation method of compound thea ethyl aromatic acid as shown in formula (I), mainly comprises the following steps:

[0039] 1, the preparation of intermediate ethyl theanine, as shown in structural formula (II);

[0040] 2. Further synthesis of thea ethyl aromatic acid by 3-carboxylic acid couma...

Embodiment 2

[0048] The difference between this embodiment and embodiment 1 is that

[0049] Step 1: Preparation of ethyl theanine

[0050] Theanine is dissolved in ethanol at a ratio of 88g / L (referring to dissolving 88g of theanine per liter of ethanol), and then slowly adding thionyl chloride to the system with a volume ratio of 56ml (referring to the dissolving solution of theanine and ethanol and two volume ratio of thionyl chloride), the mixture was stirred at room temperature for 1.5 hours, and the resulting mixture was concentrated under reduced pressure to obtain ethyl theanine of structural formula (II).

[0051] Step 2: Preparation of tea ethyl aromatic acid (TEC)

[0052] 21g of ethyl theanine was dissolved in 2.1L of anhydrous dichloromethane, 28g of 3-carboxycoumarin was added, and 0.21L of DIPEA (diisopropylethylamine) and 77g of EDCI were added respectively. The mixture was stirred at room temperature for 1.5 hours, then concentrated under reduced pressure, the solvent wa...

Embodiment 3

[0054] The difference between this embodiment and embodiment 2 is that

[0055] Step 1: Preparation of ethyl theanine

[0056] Theanine is dissolved in ethanol at a ratio of 91g / L (referring to dissolving 91g of theanine per liter of ethanol), and then slowly adding thionyl chloride to the system with a volume ratio of 57ml (referring to the dissolving solution of theanine and ethanol mixed with two volume ratio of thionyl chloride), the mixture was stirred at room temperature for 2 hours, and the resulting mixture was concentrated under reduced pressure to obtain theanine ethyl ester of structural formula (II).

[0057] Step 2: Preparation of tea ethyl aromatic acid (TEC)

[0058] 22g of ethyl theanine was dissolved in 2.2L of anhydrous dichloromethane, 32g of 3-carboxycoumarin was added, and 0.22L of DIPEA (diisopropylethylamine) and 78g of EDCI were added respectively. The mixture was stirred at room temperature for 2 hours, then concentrated under reduced pressure, the s...

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Abstract

The invention relates to the field of medical technology. Ethyl coumarin-3-carboxylyl L-theanine, a novel synthetic compound, can inhibit the growth and invasion of cancer cells of human lung cancer, breast cancer, liver cancer, gastric cancer, colon cancer, prostatic cancer, pancreatic cancer, cervical cancer, lymphadenoma, leucocythemia, melanoma, and the like, and can remarkably inhibit the growth and metastasis of the tumors in a body, with an inhibiting effect exceeding the inhibiting effects of anti-cancer drugs. The mechanism of action involves the down regulation of receptors which are closely related to growth inhibition, invasion inhibition and metastasis inhibition of tumors, signal transduction regulation and control proteins, the kinase level and combination of a nuclear factor and DNA, and also upper regulation of factors such as cancer-inhibiting proteins and cell cycle inhibition proteins. The ethyl coumarin-3-carboxylyl L-theanine can directly inhibit the activity of histone deacetylase, the activity of histonemethylferase EZH2, and combination of a inflammatory factor NF-[Kabba]B and DNA. The activity of the ethyl coumarin-3-carboxylyl L-theanine exceeds the activity of the anti-cancer drugs. The invention provides new applications of the ethyl coumarin-3-carboxylyl L-theanine in prevention and treatment of disease such as tumors, inflammation, heart and cerebral vessels and immunodeficiency.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to the use of tea ethyl aromatic acid (TEC) and its intermediate compounds 3-carboxylate coumarin (C) and theanine ethyl ester (TE) in the preparation of prevention and treatment of tumors, inflammation and heart disease. Application in disease inhibitors such as cerebrovascular disease and immunodeficiency. Background technique [0002] Abnormal growth, invasion and metastasis of malignant tumors such as human lung cancer, breast cancer, liver cancer, colon cancer, prostate cancer, pancreatic cancer, cervical cancer, lymphoma and melanoma are important causes of death of tens of thousands of patients every year. The incidence also maintains a certain level, and 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 ...

Claims

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Application Information

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IPC IPC(8): A61K31/37A61K31/198A61P35/00A61P29/00A61P9/00A61P37/00C07D311/12
Inventor 张国营关玉昆刘昆张颖吴犇昊
Owner YANTAI UNIV
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