3-[[2-(2-benzylamino) thiazole-5-yl]-methyl] quinolone-2(1H)-ketone as well as preparation and application thereof

A technology of benzimino and chlorobenzimino, applied in organic chemistry, antiviral agents, etc., can solve problems such as oseltamivir resistance

Inactive Publication Date: 2014-04-30
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, AIV is prone to resistance to oseltamivir, and it has been reported in the literature that its drug resistance is related to mutations in the neuraminidase protein

Method used

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  • 3-[[2-(2-benzylamino) thiazole-5-yl]-methyl] quinolone-2(1H)-ketone as well as preparation and application thereof
  • 3-[[2-(2-benzylamino) thiazole-5-yl]-methyl] quinolone-2(1H)-ketone as well as preparation and application thereof
  • 3-[[2-(2-benzylamino) thiazole-5-yl]-methyl] quinolone-2(1H)-ketone as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (E) Preparation of 3-[[4-tert-butyl-2-(2-hydroxybenzimino)thiazol-5-yl]methyl]quinolin-2(1H)-one

[0026] (1) Preparation of 3-(4,4-dimethyl-3-oxopent-1-en-1-yl)quinolin-2(1H)-one

[0027]15ml ethanol, 0.5g NaOH, 2.4g (0.024mol) pinacolone, reflux, add 3.46g (0.02mol) 3-formyl-2(1H)-quinolinone, monitor the reaction by TLC, react for 2h. Part of the solvent was distilled under reduced pressure, and a yellow solid was precipitated, filtered with suction, washed with 95% ethanol, and dried to obtain 3-(4,4-dimethyl-3-oxopent-1-en-1-yl)quinoline-2(1H )-ketone, yield 87.17%, melting point 209~211℃.

[0028] (2) Preparation of 3-(4,4-dimethyl-3-oxopentyl)quinolin-2(1H)-one

[0029] 3-(4,4-dimethyl-3-oxopent-1-en-1-yl) quinoline-2(1H)-one, 120ml absolute ethanol, reactant quality 5% Raney Ni, hydrogen flow in Reaction at 80°C for 8h. After the reaction is completed, filter while it is hot, let it stand, and precipitate a large amount of slightly grass-green needle-shaped ...

Embodiment 2

[0037] (E) Preparation of 3-[[4-tert-butyl-2-(2-hydroxy-3-nitrobenzimino)thiazol-5-yl]methyl]quinolin-2(1H)-one

[0038] 1mmol3-((2-amino-4-tert-butylthiazol-5-yl)methyl)quinolin-2(1H)-ketone was completely dissolved in 15ml of absolute ethanol, and after reflux, 1mmol3-nitrosalicylaldehyde and 3 drops of triethylamine were refluxed, and the reaction was monitored by TLC. React for 2 hours, cool the reaction solution to precipitate a solid, filter, wash the solid with absolute ethanol, and dry to obtain (E)-3-[[4-tert-butyl-2-(2-hydroxy-3-nitrobenzimino)thiazole -5-yl]methyl]quinolin-2(1H)-one, yield 36.8%, melting point 203~206°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.97(s, 1H, NH), 9.19(s, 1H, N=CH), 8.74(d, J=2.9Hz, 1H), 8.24(dd, J=9.2, 2.9Hz, 1H), 7.72 (t, J=8.0Hz, 2H), 7.49(t, J=7.2Hz, 1H), 7.33(d, J=8.1Hz, 1H), 7.17(t, J=7.7Hz, 1H), 7.06(d , J=9.3Hz, 1H), 4.19(s, 2H, CH 2 ), 1.41(s, 9H, 3×CH 3 ).

Embodiment 3

[0040] (E) Preparation of 3-[[4-tert-butyl-2-(2-hydroxy-5-nitrobenzimino)thiazol-5-yl]methyl]quinolin-2(1H)-one

[0041] 1mmol 3-((2-amino-4-tert-butylthiazol-5-yl)methyl)quinolin-2(1H)-ketone was completely dissolved in 15ml of absolute ethanol, and 1mmol of 5-nitrosalicylaldehyde and 3 drops of triethylamine were refluxed, and the reaction was monitored by TLC. React for 1.5h, cool the reaction solution to precipitate a solid, filter, wash the solid with absolute ethanol, and dry to obtain (E)-3-[[4-tert-butyl-2-(2-hydroxy-5-nitrobenzimino) Thiazol-5-yl]methyl]quinolin-2(1H)-one, yield 35.9%, melting point 275~278℃. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.97 (s, 1H, NH), 9.20 (s, 1H, N=CH), 8.75 (d, J=2.9Hz, 1H), 8.26 (dd, J=9.2, 3.0Hz, 1H), 7.72 (s, 1H), 7.49(t, J=7.7Hz, 1H), 7.66(d, J=7.8Hz, 1H), 7.33(d, J=8.2Hz, 1H), 7.17(t, J=7.1Hz , 1H), 7.11(d, J=9.2Hz, 1H), 4.19(s, 2H, CH 2 ), 1.41(s, 9H, 3×CH 3 ).

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Abstract

The invention relates to 3-[[2-(benzylamino) thiazole-5-yl]-methyl] quinolone-2(1H)-ketone as shown in chemical structural formulas I and II or a salt thereof. In the chemical structural formulas, R, X<1> and X<2> are selected from hydrogen, deuterium, C1-C2 alkyl, C3-C4 linear-chain alkyl or branched-chain alkyl; X<3> is selected from hydroxyl, methoxyl and ethyoxyl; is selected from hydrogen, deuterium, C1-C2 alkyl, fluorine, fluorine or bromine; X4 and X6 are selected from hydrogen, deuterium, C1-C2 alkyl, fluorine, fluorine, bromine or nitryl; X5 and X7 are selected from hydrogen, deuterium and C1-C2 alkyl. The invention also provides an application of the 3-[[2-(benzylamino) thiazole-5-yl]-methyl] quinolone-2(1H)-ketone in preparation of an influenza virus neuraminidase inhibitor.

Description

technical field [0001] The present invention relates to the preparation and application of a class of novel compounds; specifically, the preparation and application of 3-[[2-(2-benzimino)thiazol-5-yl]methyl]quinolin-2(1H)-one as an influenza Use of viral neuraminidase inhibitors. Background technique [0002] Avian influenza (AI) is a disease caused by influenza A virus, mainly invading the respiratory system. It not only affects the development of animal husbandry, but also poses a serious threat to public health and seriously affects the development of the national economy. Since it was first reported by Perroneito in Italy in 1878, AI has appeared all over the world. Avian influenza virus (AIV) belongs to type A influenza virus. According to the pathogenicity of avian influenza virus to chickens and turkeys, it is divided into three levels: high, medium, low / non-pathogenic, and can be further divided into 16 H (H 1 ~H 16 ) subtypes and 9 N (N 1 ~N 9 ) subtype, among...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06A61P31/16
CPCC07D417/06
Inventor 胡艾希方毅林林定陈爱羽刘艾林连雯雯
Owner HUNAN UNIV
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