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Diamine compound for resisting hepatitis B virus and its preparation method and its application

An amine compound and anti-hepatitis B technology, which is applied in the anti-hepatitis B virus diamine compound and its preparation and application field, can solve the problems of low glycyrrhizin content, complicated extraction and separation process, difficult quality control, etc., to achieve inhibition of hepatitis B virus, Simple synthetic route and low preparation cost

Inactive Publication Date: 2007-05-16
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional Chinese medicine licorice is a traditional liver-protecting and liver-protecting drug. Its active ingredient is glycyrrhizin. Glycyrrhizin achieves anti-virus, liver-protecting and liver-protecting effects by inhibiting HBsAg. This is the same as the diamine compound we invented this time. The mechanism of action of glycyrrhizin is similar, but the content of glycyrrhizin is low, the extraction and separation process is complicated, and the quality is difficult to control, which affects its wide application. However, the diamine compounds we invented have low synthesis cost, easy access, and are easy to provide for the majority of patients. Accepted features

Method used

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  • Diamine compound for resisting hepatitis B virus and its preparation method and its application
  • Diamine compound for resisting hepatitis B virus and its preparation method and its application
  • Diamine compound for resisting hepatitis B virus and its preparation method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1: Preparation of (Z)-N-phenyl-N-(2-N', N'-dimethyloxyaminomethyl-3-phenylallyl)acetamide;

[0058] Take 20mL ethanol, weigh 0.500g (E)-N-phenyl-N-(2-N', N'-dimethylaminomethyl-3-phenylallyl) acetamide, add to 50mL round bottom In the flask, add 0.789g of 28% hydrogen peroxide to the above mixture, react at room temperature for 10 days, remove the solvent under reduced pressure, and vacuum dry to obtain (Z)-N-phenyl-N-(2-N', N'- Dimethyloxyaminomethyl-3-phenylallyl)acetamide 0.499g, yield 95%. IR (KBr, cm -1 ): 2952, 2861, 1662, 1494, 1389, 699; 1 HNMR (CDCl 3 , ppm.): 1.88 (s, 3H), 2.53 (s, 6H), 4.28 (d, 2H), 5.12 (d, 2H), 7.02-7.43 (m, 10H), 8.02 (s, 1H).

Embodiment 2

[0059] Example 2: (Z)-N-(2-methoxyphenyl)-N-(2-N', N'-dimethyloxyaminomethyl-3-phenylallyl)acetamide preparation of

[0060] Take 20mL ethanol, weigh 0.500g (E)-N-(2-methoxyphenyl)-N-(2-N', N'-dimethylaminomethyl-3-phenylallyl) ethyl Add amide into a 50mL round bottom flask, add 0.718g28% hydrogen peroxide to the above mixture, react at room temperature for 10 days, remove the solvent under reduced pressure, and vacuum dry to obtain (Z)-N-(2-methoxybenzene Base)-N-(2-N',N'-dimethyloxyaminomethyl-3-phenylallyl)acetamide 0.492g, yield 94%. IR (KBr, cm -1 ): 2953, 2847, 1662, 1499, 1389, 752; 1 HNMR (CDCl 3 , ppm.): 1.84(s, 3H), 2.51(s, 6H), 3.715(s, 3H), 4.21-4.32(m, 2H), 4.99-5.13(m, 2H), 7.00-7.38(m, 9H), 7.91 (s, 1H).

Embodiment 3

[0061] Example 3: Preparation of (Z)-N-(4-fluorophenyl)-N-(2-N', N'-dimethyloxyaminomethyl-3-phenylallyl)acetamide ;

[0062] Take 20mL of ethanol, weigh 0.500g of (E)-N-(4-fluorophenyl)-N-(2-N',N'-dimethylaminomethyl-3-phenylallyl)acetamide, Add it into a 50mL round bottom flask, add 0.745g of 28% hydrogen peroxide to the above mixture, react at room temperature for 10 days, remove the solvent under reduced pressure, and vacuum dry to obtain (Z)-N-(4-fluorophenyl)-N -(2-N', N'-dimethyloxyaminomethyl-3-phenylallyl)acetamide 0.477g, yield 91%. IR (KBr, cm -1 ): 2956, 2863, 1639, 1508, 1383, 704; 1 HNMR (CDCl 3 , ppm.): 1.85(s, 3H), 2.54(s, 6H), 4.21-4.32(m, 2H), 4.97-5.17(m, 2H), 6.70(s, 1H), 7.02-7.43(m, 9H).

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Abstract

The invention discloses a diamine compound of anti-hepatitis B virus and preparing method and application with structure as formula (I), which is characterized by the following: adopting compound in the structural formula (II) as raw material; oxidizing directly; fitting for preparing the drug to prevent or treat relative disease of anti-hepatitis B virus.

Description

technical field [0001] The invention relates to a preparation method and application of a class of anti-hepatitis B virus diamine compound, which belongs to the anti-hepatitis B virus compound and its synthesis method and application. Background technique [0002] Hepatitis B surface antigen, referred to as HBsAg, exists in the outer shell of hepatitis B virus. The detection of HBsAg in serum is one of the early diagnostic indicators of hepatitis B. After hepatitis B virus infection, most people have no clinical manifestations, but HBsAg can be detected in the blood. These people are usually called HBsAg carriers. Hepatitis B e antigen, referred to as HBeAg for short, is the soluble component of HBcAg. HBeAg is associated with the virus Dane particles and hepatitis B virus DNA, and is a serological indicator of active hepatitis B virus replication. Positive serum HBeAg indicates strong infectivity. After the liver cells are invaded by the hepatitis B virus, the hepatitis B...

Claims

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Application Information

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IPC IPC(8): C07C233/36C07C231/14A61K31/16A61P1/16A61P31/12
Inventor 李春葆李享
Owner TIANJIN UNIV
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