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3-[[2-(2-Benzylhydrazono)thiazol-5-yl]methyl]quinolin-2(1h)-one and its preparation and application

A quinoline and methyl technology, applied in the field of preparation and application of new compounds, can solve problems such as oseltamivir resistance

Inactive Publication Date: 2015-10-07
HUNAN UNIV
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  • Summary
  • 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-Benzylhydrazono)thiazol-5-yl]methyl]quinolin-2(1h)-one and its preparation and application
  • 3-[[2-(2-Benzylhydrazono)thiazol-5-yl]methyl]quinolin-2(1h)-one and its preparation and application
  • 3-[[2-(2-Benzylhydrazono)thiazol-5-yl]methyl]quinolin-2(1h)-one and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of 3-[[4-tert-butyl-2-(2-hydroxybenzylhydrazono)thiazol-5-yl]methyl]quinolin-2(1H)-one

[0027] (1) Preparation of 3-(4,4-dimethyl-3-oxopent-1-en-1-yl)quinolin-2(1H)-one

[0028] 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℃.

[0029] (2) Preparation of 3-(4,4-dimethyl-3-oxopentyl)quinolin-2(1H)-one

[0030] 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-shap...

Embodiment 2

[0036] Preparation of 3-[[4-tert-butyl-2-(2-hydroxy-5-chlorobenzylhydrazono)thiazol-5-yl]methyl]quinolin-2(1H)-one

[0037] 1mmol 3-(2-bromo-4,4-dimethyl-3-oxopentyl)quinolin-2(1H)-one, 1mmol2-(2-hydroxy-5-chlorobenzylhydrazono)thio Amide and 15ml of ethanol were refluxed, and the reaction was monitored by TLC. React for 3h, cool the reaction liquid, precipitate solid, filter, recrystallize the crude product with absolute ethanol, and dry to obtain 3-[[4-tert-butyl-2-(2-hydroxy-5-chlorobenzylhydrazono)thiazole-5 -yl]methyl]quinolin-2(1H)-one, yield 58.7%, melting point 251~254°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.93(s, 1H, NH), 10.41(br, 1H, OH), 8.21(s, 1H, N=CH), 7.67(d, J=7.2Hz, 1H), 7.57(s, 1H) , 7.52(s, 1H), 7.47(t, J=7.2Hz, 1H), 7.31(d, J=8.4Hz, 1H), 7.21(dd, J=2.8Hz, J=2.4Hz, 1H), 7.15 (t, J=7.2Hz, 1H), 6.88(d, J=8.8Hz, 1H), 3.99(s, 2H, CH 2 ), 1.32(s, 9H, 3×CH 3 ).

Embodiment 3

[0039] Preparation of 3-[[4-tert-butyl-2-(2-hydroxy-5-bromobenzylhydrazono)thiazol-5-yl]methyl]quinolin-2(1H)-one

[0040] 1mmol 3-(2-bromo-4,4-dimethyl-3-oxopentyl)quinolin-2(1H)-one, 1mmol2-(2-hydroxy-5-bromobenzylhydrazono)thio Amide and 15ml of ethanol were refluxed, and the reaction was monitored by TLC. React for 2 hours, distill part of the solvent under reduced pressure, cool the reaction solution, precipitate solid, filter, wash with 95% ethanol, and dry to obtain 3-[[4-tert-butyl-2-(2-hydroxy-5-bromobenzylhydrazono) Thiazol-5-yl]methyl]quinolin-2(1H)-one, yield 78.4%, melting point 259~261℃. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.91(s, 1H, NH), 10.42(br, 1H, OH), 8.19(s, 1H, N=CH), 7.67(d, J=10.8Hz, 2H), 7.56(s, 1H) , 7.56(t, J=7.6Hz, 1H), 7.33-7.30(m, 2H), 7.15(t, J=7.2Hz, 1H), 6.83(d, J=8.4Hz, 1H), 3.99(s, 2H, CH 2 ), 1.31(s, 9H, 3×CH 3 ).

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Abstract

The invention relates to a 3-[[2-(2-benzyl hydrazono) thiazole-5-base] methyl] quinoline-2 (1H)-ketone shown in a chemical structural formula I or a salt therefore as shown in description, wherein R, X1 and X2 are selected from hydrogen, deuterium, C1-C2 alkyls, and C3-C4 linear alkyls or branched alkyls; X3 is selected from hydrogen, deuterium, C1-C2 alkyls, hydroxyl, methoxyl and oxethyl; X4 is selected from hydrogen, deuterium, C1-C2 alkyls, fluorine, chlorine or bromine; X5 and X6 are selected from hydrogen, deuterium, C1-C2 alkyls, fluorine, chlorine, bromine or nitrocellulose; X7 is selected from hydrogen, deuterium, and C1-C2 alkyls; the invention also discloses application of the 3-[[2-(2-benzyl hydrazono) thiazole-5-base] methyl] quinoline-2 (1H)-ketone in preparing an influenza virus neuraminidase inhibitor.

Description

technical field [0001] The present invention relates to the preparation and application of a class of new compounds; specifically, the preparation and application of 3-[[2-(2-benzylhydrazono)thiazol-5-yl]methyl]quinolin-2(1H)-one Use of Influenza Virus 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 t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06A61K31/4709A61P31/16
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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