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A class of 6-arylbenzo[4,5]imidazo[1,2-a]quinolone derivatives and their preparation methods and applications

An imidazo and derivative technology is applied in the application field of preparing anti-influenza virus drugs, and achieves the effects of simple process, reliable and stable source, and great potential for popularization and application.

Active Publication Date: 2017-12-29
SOUTH CHINA SEA INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But in some cases of severe infection, chemical drugs have to be used to treat such viruses

Method used

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  • A class of 6-arylbenzo[4,5]imidazo[1,2-a]quinolone derivatives and their preparation methods and applications
  • A class of 6-arylbenzo[4,5]imidazo[1,2-a]quinolone derivatives and their preparation methods and applications
  • A class of 6-arylbenzo[4,5]imidazo[1,2-a]quinolone derivatives and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the synthesis of compound 1

[0020]

[0021] 50mg (0.2mmol, 1.0eq.) of 2-benzimidazolyl-benzaldehyde, 96μL (0.8mmol, 4.0eq.) of benzyl bromide, and Cs 2 CO 3 216mg (0.8mmol, 4.0eq) was reacted in DMF at 130°C for 6h, cooled to room temperature after completion, DMF was evaporated by rotary evaporation, and 100mL water was added, extracted with 30mL ethyl acetate each time, three times in total, ethyl acetate extraction The phases (organic layer) were combined and dried. After removing ethyl acetate, the residue was subjected to silica gel column chromatography to obtain 45 mg of the target compound (compound 1, whose structural formula is shown in formula 1), with a yield of 52%.

[0022] The NMR data of compound 1 are as follows:

[0023] 1 H NMR (500MHz, CDCl 3 )δ8.66(dd, J=8.0,1.5Hz,1H),8.47(d,J=8.5Hz,1H),8.03(s,1H),7.80(ddd,J=8.6,7.2,1.6Hz,1H ),7.52(t,J=7.5Hz,1H),7.26–7.22(m,1H),7.21–7.14(m,7H),6.87(s,1H),6.70(d,J=6.5Hz,2H) ,4.84(s,2H),2.46(...

Embodiment 2

[0024] Embodiment 2: the synthesis of compound 2

[0025]

[0026] 4-fluorobenzyl bromide was replaced by benzyl bromide, and the synthesis method was the same as in Example 2 to obtain the target compound (compound 2, whose structural formula is shown in formula 2), with a yield of 22%.

[0027] The NMR data of compound 2 are as follows:

[0028] 1 H NMR (500MHz, CDCl 3 )δ8.62(d, J=7.9Hz, 1H), 8.45(d, J=8.5Hz, 1H), 8.02(s, 1H), 7.78(t, J=7.7Hz, 1H), 7.50(t, J=7.5Hz, 1H), 7.14(dd, J=8.0, 5.7Hz, 2H), 6.88(dd, J=14.8, 7.2Hz, 5H), 6.72–6.61(m, 2H), 4.84(s, 2H ),2.46(s,3H),2.31(s,3H). 13 C NMR (125MHz, CDCl 3 )δ174.00,163.15,163.10,161.19,161.14,146.11,135.52,133.71,133.64,133.03,131.61,131.12,130.89,129.70,129.68,127.97,127.24,127.12,127.06,125.47,124.53,115.64,115.47,115.36,115.13 ,114.96,114.44,110.43,101.34,47.38,20.57,20.24.HRMS-ESI(m / z):Calcd for C 30 h 2 f 2 N 2 O[M+H] + 465.1773, found 465.1783.

Embodiment 3

[0029] Embodiment 3: the synthesis of compound 3

[0030]

[0031] 50 mg (0.2 mmol, 1.0 eq.) of 2-benzimidazolyl-benzaldehyde, 87 μL (0.6 mmol, 3.0 eq.) of 3,4-dichlorobenzyl bromide, and K 2 CO 3 83mg (0.6mmol, 3.0eq) was reacted in DMF at 130°C for 4h, cooled to room temperature after completion, DMF was removed by rotary evaporation, and 100mL water was added, extracted with 30mL ethyl acetate each time, three times in total, the organic layers were combined and dried , after removing ethyl acetate, the residue was subjected to silica gel column chromatography to obtain 50 mg of the target compound (compound 3, whose structural formula is shown in formula 3), yield: 44%.

[0032] The NMR data of compound 3 are as follows:

[0033] 1 H NMR (u500MHz, CDCl 3)δ8.59(d, J=7.9Hz, 1H), 8.45(d, J=8.5Hz, 1H), 8.05(s, 1H), 7.81(t, J=7.8Hz, 1H), 7.53(t, J=7.5Hz, 1H), 7.35–7.27(m, 2H), 7.16(s, 1H), 7.10(d, J=8.2Hz, 1H), 6.88(s, 1H), 6.81(s, 1H), 6.55(d,J=8.2Hz,1H),4.85(d,J=2.9...

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Abstract

The invention discloses a 6-arylbenzo[4,5]imidazo[1,2-a]quinolone derivative, a preparation method therefor and an application of the 6-arylbenzo[4,5]imidazo[1,2-a]quinolone derivative. The 6-aryl substituted benzo[4,5]imidazo[1,2-a]quinolone derivative is characterized by having a structural formula represented by a formula (I) shown in the description, wherein R is H, mono- or multi-substituted methyl, a chlorine atom, a fluorine atom or trifluoromethyl. The 6-arylbenzo[4,5]imidazo[1,2-a]quinolone derivative disclosed by the invention has influenza virus inhibition activity. Furthermore, the invention discloses a preparation method for the 6-arylbenzo[4,5]imidazo[1,2-a]quinolone derivative. The preparation method is simple in process and low in cost and is suitable for large-scale production, and the source is reliable and stable. The 6-arylbenzo[4,5]imidazo[1,2-a]quinolone derivative disclosed by the invention has influenza virus inhibition activity, so that the derivative can be used for preparing influenza virus drugs and applied to the aspect of influenza virus research, and the potential of popularization and application is great.

Description

Technical field: [0001] The invention belongs to the field of chemical and pharmaceutical preparations, in particular to a class of novel 6-arylbenzo[4,5]imidazo[1,2-a]quinolone derivatives and their preparation methods and their application in the preparation of anti-influenza virus drugs . Background technique: [0002] As we all know, influenza virus is a dangerous species that spreads widely, mutates rapidly, and causes great damage. In general, people can strengthen physical exercise to improve their ability to resist virus invasion by improving their own immunity. But in some cases of severe infection, chemical drugs have to be used to treat such viruses. At present, the chemical drugs for the treatment of influenza virus are mainly divided into two categories, one is ion channel (M2) inhibitors such as amantadine; the other is the inhibitor developed for virus ceramidase. Although the influenza virus family has been raging around the world for a century, there are ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61K31/437A61P31/16
CPCC07D471/04
Inventor 廖升荣刘永宏
Owner SOUTH CHINA SEA INST OF OCEANOLOGY - CHINESE ACAD OF SCI