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Polymethoxyflavone derivatives with anti-hepatitis A virus activity, preparation method and application thereof

A technology for polymethoxyflavonoids and hepatitis A virus, which is applied in the directions of antiviral agents, organic active ingredients, medical preparations containing active ingredients, etc., can solve the problem of metabolic instability and limited content of polymethoxyflavonoids , low bioavailability and other problems, to achieve the effect of high research value and high clinical application prospects

Active Publication Date: 2022-04-22
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the structural characteristics of flavonoids themselves, their oral bioavailability is very low and their metabolism is very unstable, which limits the natural flavonoids to be difficult to be directly developed into drugs. It can greatly improve its metabolic stability and cell membrane permeability, thereby promoting absorption and greatly improving bioavailability (Enzyme and Microbial Technology, 2016, 86:103-116)
However, the content of polymethoxylated flavonoids from natural sources is very limited, which limits their application in drug development

Method used

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  • Polymethoxyflavone derivatives with anti-hepatitis A virus activity, preparation method and application thereof
  • Polymethoxyflavone derivatives with anti-hepatitis A virus activity, preparation method and application thereof
  • Polymethoxyflavone derivatives with anti-hepatitis A virus activity, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: the preparation of compound SSC2

[0058]

[0059] Add intermediate compound K (30mg, 0.074mmol), 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate into a 25mL eggplant-shaped bottle (28.1mg, 0.074mmol), diethylamine (9mg, 0.111mmol), N,N-diisopropylethylamine (9.5mg, 0.074mmol), dry DMF 10mL, react at 60°C for 10h. After the reaction was completed, it was extracted with water and saturated brine in sequence, and the organic layer was separated, dried, filtered and concentrated to obtain an oil, which was purified by silica gel column chromatography to obtain the target product SSC2.

[0060] The structural identification data are as follows: 1 H NMR (600MHz, CDCl 3 ):δ6.64(s,2H),6.22(d,J=2.35Hz,1H),6.09(d,J=2.35Hz,1H),4.86(dd,J=10.79,1.85Hz,1H),4.63 (s,2H)3.88(s,6H,OCH 3 ),3.85(s,3H,OCH 3 ),3.81(s,3H,OCH 3 ), 3.05(s,3H), 2.98(s,3H), 2.78(m,1H), 2.63(m,1H), 2.17(m,1H), 2.00(m,1H).

Embodiment 2

[0061] Embodiment 2: the preparation of compound SSC8

[0062]

[0063] Add intermediate compound K (30 mg, 0.074 mmol), tetramethoxysilane (22.5 mg, 0.148 mmol), p-chloroaniline (14 mg, 0.111 mmol), toluene 10 mL, and react at 100 ° C for 10 h in a 25 mL eggplant-shaped bottle. After the reaction was completed, it was extracted with water and saturated saline in sequence, the organic layer was separated, dried, filtered and concentrated to give a light yellow powder, which was purified by silica gel column chromatography to obtain the target product SSC8.

[0064] The structural identification data are as follows: 1 H NMR (600MHz, CDCl 3 ):δ8.22(s,N-H),7.55(d,J=7.94Hz,2H),7.05(d,J=22.61Hz,2H),6.64(s,2H),6.19(d,J=2.37Hz ,1H),6.17(d,J=2.37Hz,1H),4.90(dd,J=10.70,1.90Hz,1H),4.57(s,2H),3.88(s,6H,OCH 3 ),3.85(s,3H,OCH 3 ),3.84(s,3H,OCH 3 ),2.80(ddd,J=16.80,5.57,2.37Hz,1H),2.65(m,1H),2.20(ddt,J=13.59,6.11,2.18Hz,1H),2.01(dtd,J=13.71,11.53 ,5.67Hz,1H).

Embodiment 3

[0065] Embodiment 3: the preparation of compound SSC15

[0066]

[0067] Add intermediate compound L (30 mg, 0.072 mmol), 5-chlorothiophene-2-carbaldehyde (16.0 mg, 0.111 mmol), 10 mL of ethanol, and catalytic amount of glacial acetic acid into a 25 mL eggplant-shaped bottle, and heat to reflux for 10 h. After the reaction was completed, it was extracted with water and saturated brine in sequence, the organic layer was separated, dried, filtered and concentrated to obtain an oily compound, which was purified by silica gel column chromatography to obtain the target product SSC15.

[0068] The structural identification data are as follows: 1 H NMR (600MHz, DMSO-d 6 ): δ11.62 (ds, 1H, isomer a), 11.56 (ds, 1H, isomer b), 8.48 (s, 1H, isomer a), 8.07 (s, 1H, isomer b ), 7.34 (d, 1H, J = 3.98Hz isomer a), 7.32 (d, 1H, J = 3.95Hz isomer b), 7.16 (d, 1H, J = 3.94Hz isomer a), 7.13 (d, 1H, J = 3.94Hz isomer b), 6.72 (s, 4H, isomer a, b), 6.25 (d, J = 2.28Hz, 1H, isomer a), 6.17 ...

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Abstract

The invention belongs to the field of medicinal chemistry, and relates to a class of polymethoxyflavone derivatives with anti-hepatitis A virus activity, a preparation method and application thereof. The polymethoxyflavone derivatives have the structure shown in formula (I) or formula (II). Antiviral drug screening for hepatitis A virus replication by applying a visualized drug screening model found that the polymethoxyflavone derivatives of the present invention have good anti-hepatitis A virus activity and can be further used to develop drugs for the treatment of hepatitis A .

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a class of polymethoxyflavone derivatives with anti-hepatitis A virus activity, a preparation method and application thereof. Background technique [0002] Hepatitis A (Hepatitis A for short) is an acute intestinal infectious disease mainly caused by liver damage caused by Hepatitis A virus (HAV) of the Picornaviridae Hepavirus genus. Clinically, the main symptoms are chills, fever, nausea, fatigue, loss of appetite, hepatomegaly, abnormal liver function, dark urine and jaundice. Although HAV infection is mostly self-limited and does not cause chronic infection, it can lead to death in severe cases. In addition, HAV usually spreads widely through fecal-oral infection, and the human body usually cannot obtain long-lasting immunity. About 200 million people are infected with hepatitis A virus in the world every year, 30 million of whom will develop symptoms, and 30,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/60C07D405/12C07D409/12A61K31/353A61K31/4025A61K31/4545A61K31/4433A61K31/381A61P31/14
CPCC07D311/60C07D405/12C07D409/12A61P31/14Y02A50/30
Inventor 宋少江刘庆博史绍春村松正道郑鑫
Owner SHENYANG PHARMA UNIVERSITY
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