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Phenanthridine derivative as well as medicinal composition, preparation method and application thereof

The technology of a compound and general formula is applied in the application field of preparing anti-hepatitis C and hepatitis B virus drugs, and can solve the problems of no phenanthridine derivatives, no anti-hepatitis B and anti-hepatitis C activity, etc.

Active Publication Date: 2013-06-12
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, so far, there is no report on the phenanthridine derivatives in the benzylphenethylamine alkaloids in the prior art, and there is no report that they have anti-hepatitis B and anti-hepatitis C activities

Method used

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  • Phenanthridine derivative as well as medicinal composition, preparation method and application thereof
  • Phenanthridine derivative as well as medicinal composition, preparation method and application thereof
  • Phenanthridine derivative as well as medicinal composition, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of compounds of general formula (1):

[0044] (1) Experimental conditions.

[0045] ESI and high-resolution mass spectrometry were determined by Finnigan MAT 90 and VG Auto Spec-3000 mass spectrometer; melting point was determined by X-4 melting point instrument (Yuhua Experimental Equipment Factory, Gongyi, Henan); nuclear magnetic spectrum was determined by Bruker AM-400, DRX- 500 and Avance III 600 NMR analyzers, deuterated chloroform and deuterated DMSO as solvents, Me 4 Si as internal standard; Silica gel: 60-80 mesh, 300-400 mesh (Shandong Qingdao Ocean Chemical Company); Silica gel plate: Pre-coated silica gel 60 F 254 (Merck, Darmstadt, Germany); HPLC: Hypersil Gold RP-C 18 column (Thermo Fisher Scientific Inc., Waltham, Massachusetts, USA); reagents, solvents: Aldrich-sigma Chemical Co., Acros Organics and J&K Scientific.

[0046] (2) Total synthesis of the compound of general formula (1):

[0047]

[0048] Reagents and conditions: a. NaHCO ...

Embodiment 2

[0054] Synthesis of Specific Compounds:

[0055] (1) 2-bromo-4,5-dimethoxybenzoic acid (13): 2-bromo-4,5-dimethoxybenzaldehyde (250mg, 1mmol), sodium bicarbonate (200mg) and potassium permanganate ( 500 mg) was dissolved in water (20 mL), heated and stirred for 3 hours, then extracted twice with 20 mL of dichloromethane, combined organic phases, washed with saturated ammonium chloride solution and saturated brine, and dried overnight with anhydrous magnesium sulfate, After filtration, the excess solvent was evaporated, and the residue was purified by silica gel column chromatography to obtain compound 13 (220 mg, yield: 85%) as a light yellow solid.

[0056] (2) 2-bromo-4,5-dimethoxy-N-methyl-Benzenemethanamine (14): Dissolve compound 13 (260 mg, 1 mmol) in THF (10 mL), then add DMF (0.1 mL) and thionyl chloride (0.5mL, 4mmol), the reaction solution was stirred at 50°C for 2 hours, then the excess THF was evaporated under reduced pressure, and the residue was added dropwise t...

Embodiment 3

[0106] Anti-hepatitis C virus (HCV) activity of the compounds of the present invention:

[0107] (1) Experimental method

[0108] (1) Toxicity test of compounds on Huh7.5 cells:

[0109] 1×10 5 / mL Huh7.5 cells were seeded in 100 μL in a 96-well plate, at 37 °C, 5 % CO 2 After culturing in an incubator under saturated humidity conditions for 24 hrs, different concentrations of the compound solution of the present invention and positive control drug (VX-950) were added, and after continuing to culture for 72 hrs, 10 μL of 5 mg / mL was added to each well MTT, continue to culture for 4 hrs, after lysing with DMSO, measure OD on a microplate reader 570-630 mm Compared with the OD value of the cell control group, the toxicity inhibition rate of each concentration to the cells was calculated, and the half toxic concentration of the drug to the cells was calculated by the Reed-Muench method.

[0110] (2) Anti-HCV activity of the compound in cell culture:

[0111] 1×10 5 / mL Huh7...

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Abstract

The invention provides a phenanthridine compound with an effect of resisting hepatitis B and hepatitis C, a medicinal composition taking the same as an active medicine component, a preparation method and applications of the phenanthridine compound in preparing a medicine for resisting hepatitis C viruses, and preparing an anti-virus medicine. According to the invention, the activity of benzylphenethylamine alkaloid in resisting various viruses is discovered in a process of studying a plant anti-virus natural product, and an obvious effect in resisting viruses of hepatitis B and hepatitis C of a phenanthridine derivative is discovered through structure modification, structure-function relationship and structure optimization.

Description

Technical field: [0001] The invention belongs to the field of medicines, and in particular relates to phenanthridine compounds, their pharmaceutical compositions as active ingredients of medicines, their preparation methods, and their application in the preparation of anti-hepatitis C and hepatitis B virus medicines. Background technique: [0002] The World Health Organization estimates that there are approximately 2 billion hepatitis B virus (hepatitis B virus, HBV) infected persons in the world, of which 350-400 million are HBV chronically infected persons, and the number of deaths due to acute and chronic HBV infection reaches 113.13 million each year, and Upward trend. my country is a big country with hepatitis B, accounting for 1 / 3 of them, with 120 million HBV carriers. It is known from the data that hepatitis B virus infection has become an important disease that endangers human health. Therefore, effective anti-HBV treatment for HBV-infected patients is particularly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/12C07F7/18A61K31/473A61K31/695A61P1/16A61P31/20A61P31/14
Inventor 郝小江陈铎之尹俊林彭宗根何红平蒋建东邸迎彤张于李顺林
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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