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

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...

Examples

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).

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...

Examples

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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