Application of ethyl 6-chlorocoumarin-3-carboxylyl L-theanine and the like in preparation of product used for preventing and treating disease such as cancers

The technology of theanine chloroaromatic amide and theanine ethyl ester is applied in the medical field, can solve the problems of toxic and side effects, limited prevention and treatment, and achieves the effects of less toxic and side effects, enhanced curative effect and wide application.

Inactive Publication Date: 2014-04-02
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 6-chlorocoumarin-3-carboxylyl L-theanine and the like in preparation of product used for preventing and treating disease such as cancers
  • Application of ethyl 6-chlorocoumarin-3-carboxylyl L-theanine and the like in preparation of product used for preventing and treating disease such as cancers
  • Application of ethyl 6-chlorocoumarin-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

[0038] A compound for treating tumors in this embodiment, its name is (R)-ethyl ester-2-(6-Cl-2-O-2H-benzopyran-3-carboxy)-5-(ethylamino) -5-oxopentanoic acid ester, referred to as theanine chloroaromatic amide (TClC), 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 melting point decomposes above 242 ° 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 chloro-aromatic amide as shown in formula (I), mainly comprises the following steps:

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

[0043] 2, the preparat...

Embodiment 2

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

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

[0055] (1) Add 205g of 5-chlorosalicylaldehyde, 205mL of diethyl malonate, 610mL of absolute ethanol, 11mL of hexahydropyridine and 1-1.3ml of glacial acetic acid; (3) Add about 610mL of cold water (0°C), filter with suction after crystallization and wash twice with 110mL of 50% ethanol cooled by ice water (0°C), to obtain 6- Chlorocoumarin-3-condensed ester; (4) add 128g of 6-chlorocoumarin-3-carboxylate ethyl ester and 103g sodium hydroxide respectively, then add 510ml absolute ethanol and 510mL water, 80 ℃ water bath Under certain conditions, heat to reflux for about 2.5 hours; (5) After the reaction is completed, immediately place it in an ice bath at 0°C, add concentrated hydrochloric acid (HCL content: 36-38%), and make the pH of the system between 2-3, and the system will The solid precipitated, was filtered after cooling in an ice b...

Embodiment 3

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

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

[0063] (1) Add 210g of 5-chlorosalicylaldehyde, 210mL of diethyl malonate, 615mL of absolute ethanol, 12mL of hexahydropyridine and 1-1.3ml of glacial acetic acid; (3) Add about 615mL of cold water (0°C), filter with suction after crystallization and wash twice with 115mL of 50% ethanol cooled by ice water (0°C), to obtain 6-chloro Coumarin-3-condensed ester; (4) Add 132g and 106g sodium hydroxide respectively, then add 515ml absolute ethanol and 515mL water, 80 ℃ water bath conditions (5) Immediately after the reaction is completed, put it in an ice bath at 0°C, add concentrated hydrochloric acid (HCL content: 36-38%), and make the pH of the system between 2-3, and the system will precipitate solids , filtered after cooling in an ice bath, washed with a small amount of ice water, and the dried crude product was purified by recrystalliz...

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Abstract

The invention relates to the field of medical technology. Ethyl 6-chlorocoumarin-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 inhibition of the bonding of the receptors which are closely related to growth, invasion and metastasis of the tumors, signal transduction regulation and control proteins, the kinase level and a nuclear factor with DNA, and also upper regulation of factors such as cancer-inhibiting proteins and cell cycle inhibition proteins. The ethyl 6-chlorocoumarin-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 6-chlorocoumarin-3-carboxylyl L-theanine exceeds the activity of clinical anti-cancer drugs. The invention provides new applications of the ethyl 6-chlorocoumarin-3-carboxylyl L-theanine in prevention and treatment of diseases 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 preparation of theanine chloroaromatic amide (TClC) and its intermediate compound 6-chloro-3-carboxylic acid coumarin (CLC) and theanine ethyl ester (TE). Application in the treatment of tumors, inflammation, cardiovascular and cerebrovascular diseases and immunodeficiency and other disease inhibitors. 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 ethyla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/37A61K31/225A61P35/00A61P35/02A61P35/04A61P29/00A61P9/00A61P37/02
Inventor 张国营姚建文刘昆张颖吴犇昊
Owner YANTAI UNIV
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