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Acrylamide compound and preparation method and medical application thereof

A compound and propylamine-based technology, applied in the fields of medicinal chemistry and pharmacotherapeutics, can solve problems such as inability to completely eliminate viruses, low sustained response rate of interferon, and drugs that cannot meet the needs of treatment, etc.

Active Publication Date: 2017-08-04
XUZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, interferon has disadvantages such as low sustained response rate and many side effects
[0005] In summary, although there are many anti-HBV drugs clinically, due to the complexity of the etiology of hepatitis B, the "rebound" caused by the inability of drugs to completely clear the virus, the drug resistance of the virus, and the toxic and side effects of drugs, etc., Existing drugs still do not meet treatment needs

Method used

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  • Acrylamide compound and preparation method and medical application thereof
  • Acrylamide compound and preparation method and medical application thereof
  • Acrylamide compound and preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080](S,E)-N-{1-bromo-3-[(1-hydroxy-3-phenyl)-2-propylamino]-3-oxo-1-phenylpropen-2-yl}benzyl Amide (I 1 )

[0081] Glycine (0.75g, 0.01mol) was dissolved in sodium hydroxide (1.2g, 0.03mol) solution, cooled to 0°C in an ice-water bath, benzoyl chloride (2.34mL, 0.02mol) was added dropwise, and after stirring for half an hour, the reaction After the solution was returned to room temperature, hydrochloric acid solution was added until a large amount of white solids were precipitated, the pH was adjusted to about 2, the solids were filtered out, the solids were washed with water for several times, and then dried into white powder solid benzoylglycine (1.492g, 83%). Add acetic anhydride (1.5mL) to three mixtures of benzoylglycine (0.537g, 3mmol), anhydrous sodium acetate (0.246g, 3mmol), and benzaldehyde (0.306mL, 3mmol). Condensate under reflux for 3 hours, extract with dichloromethane after cooling, wash the organic layer with saturated brine and saturated sodium bicarbonate...

Embodiment 2

[0086] (S,E)-N-{1-bromo-3-[(1-hydroxy-3-phenyl)-2-propylamino]-1-(4-hydroxyphenyl)-3-oxo-1- Propylene-2-yl}benzamide (I 2 )

[0087] According to the similar method of Example 1, use benzoylglycine (2.02g, 11.3mmol), p-hydroxybenzaldehyde (1.38g, 11.3mmol) to react to obtain (Z)-4-(4-hydroxybenzylidene)-2 -Phenyloxazol-5(4H)-one (2.358g, 78.7%); (Z)-4-(4-hydroxybenzylidene)-2-phenyloxazol-5(4H)-one (3.684 g, 13.9mmol) and L-phenylalaninol (2.1g, 13.9mmol) were reacted for 20h, and an appropriate amount of bromine solution was added dropwise to obtain the yellow title compound (3.6g, 18%).

[0088] m.p.220℃-224℃;

[0089] ESI-MS: m / z 495[M+H] + ;

[0090] 1H-NMR (DMSO, 400MHz, δppm): 2.80-2.96(m, 2H, CH2), 3.41-3.52(m, 2H, CH2), 4.11-4.26(m, 1H, CH), 6.81-6.86(d, 2H,J=8.8Hz,Ar-H),7.10-7.16(m,1H,Ar-H),7.19-7.30(m,4H,Ar-H),7.53-7.59(m,3H,Ar-H) ,7.93-7.98(d,1H,J=8.8Hz,Ar-H),8.04-8.09(m,1H,Ar-H),8.13-8.17(m,2H,Ar-H),8.59-8.60(s ,1H,NH),9.93-10.04(s,1H,OH),10.51-10.55(s,1H,N...

Embodiment 3

[0092] (S,Z)-2-fluoro-N-{3-[(1-hydroxy-3-phenyl)-2-propylamino]-3-oxo-1-phenylpropen-2-yl}benzyl Amide (I 3 )

[0093] Glycine (3.75g, 0.05mol) was dissolved in sodium hydroxide (6g, 0.15mol) solution, cooled to 0°C in an ice-water bath, o-fluorobenzoyl chloride (6mL, 0.05mol) was added dropwise, stirred for 1 hour, and the reaction After the solution returns to room temperature, add hydrochloric acid solution until a large amount of white solids are precipitated, adjust the pH to about 2, filter the precipitated solids, wash the solids with water several times, and dry them into white powder solid o-fluorobenzoylglycine (2.64g, 27% ). Add 1 mL of acetic anhydride to three mixtures of o-fluorobenzoylglycine (1.93 g, 0.01 mol), anhydrous sodium acetate (0.82 g, 0.01 mol), and benzaldehyde (1.02 mL, 0.01 mol), Condensate in the bath and reflux for 4 hours, extract with dichloromethane, wash the organic layer with saturated brine and saturated sodium bicarbonate solution, dry ...

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Abstract

The invention discloses an acrylamide compound and a preparation method and medical application thereof, and relates to a compound shown in formula I and an isomer or a pharmaceutically acceptable salt thereof. The acrylamide compound and the isomer or the pharmaceutically acceptable salt thereof can be applied to prepare HBV (hepatitis B virus)-resistant medicines. The formula is shown in the specification.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to a class of acrylamide compounds. The compounds can be used to prepare medicines with anti-hepatitis B virus (HBV) effect. The present invention also relates to the preparation method of the compounds and the pharmaceutical combination containing them. Background technique [0002] Hepatitis B is an infectious disease caused by hepatitis B virus (HBV) and presents a chronic carrier state. Chronic hepatitis B has a poor prognosis and can develop into liver cirrhosis and primary liver cancer, seriously endangering human health. Currently clinically used anti-HBV drugs mainly include HBV DNA polymerase / reverse transcriptase inhibitor nucleoside analogues and immunomodulator interferon. [0003] Nucleoside analogues are a series of drugs derived from nucleosides as the basic framework through structural changes in bases or pentose rings, such as lamivudi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/87C07C235/34C07C231/10C07C231/12C07C253/30C07C255/60A61K31/166A61K31/277A61P31/20
CPCC07C233/87C07C235/34C07C255/60
Inventor 邱净英龚奇能谷小珂陈旺高剑黄健航
Owner XUZHOU MEDICAL UNIV
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