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Application of 2-[5-(azole-1-yl)thiazole-2-imino]-5-benzal-4-thaizolidinone as NA inhibitor

A technology of thiazolinone and imino, applied in antiviral agents, organic chemistry, etc.

Active Publication Date: 2017-01-11
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, studies have found that some virus strains are resistant to Oseltamivir

Method used

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  • Application of 2-[5-(azole-1-yl)thiazole-2-imino]-5-benzal-4-thaizolidinone as NA inhibitor
  • Application of 2-[5-(azole-1-yl)thiazole-2-imino]-5-benzal-4-thaizolidinone as NA inhibitor
  • Application of 2-[5-(azole-1-yl)thiazole-2-imino]-5-benzal-4-thaizolidinone as NA inhibitor

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of 2-{[4-tert-butyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-yl]imino}-4-thiazolinone (2)

[0020]

[0021] 11.25g (50mmol) 4-tert-butyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine, 100mL dichloromethane, stirred and dissolved, added 6.90g (50mmol) without Potassium carbonate in water, stirred at room temperature for 30 minutes, added dropwise 4.0ml (50 mmol) of chloroacetyl chloride, and reacted at room temperature for 2.5 hours. The reaction solution was poured into ice water, extracted with dichloromethane, washed with saturated aqueous sodium carbonate, combined organic phases, dried over anhydrous sodium sulfate, precipitated, and recrystallized from ethanol to obtain 13.50 g of white solid 1, yield 93%, m.p.130-133 ℃.

[0022] Dissolve 10.25g of compound 1, 4.95g of potassium thiocyanate in 100ml of ethanol, and heat to reflux for 5.0h. After cooling, a solid was precipitated, filtered with suction, and dried to obtain 9.50 g of light yellow solid 2-{[4-te...

Embodiment 2

[0024] 2-{[4-tert-butyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-yl]imino}-5-(4-cyanobenzylidene)- Preparation of 4-thiazolinone

[0025]

[0026] 30ml of acetic acid, 12.0mmol of sodium acetate, 4.0mmol of intermediate 2 and 8.0mmol of 4-cyanobenzaldehyde were heated under reflux for 10h. Cool, pour into saturated brine, filter with suction, wash with water, and recrystallize from ethanol to obtain a yellow solid 2-{[4-tert-butyl-5-(1H-1,2,4-triazol-1-yl)thiazole-2 -yl]imino}-5-(4-cyanobenzylidene)-4-thiazolinone, yield 75%, m.p.250~253°C. 1 H NMR (DMSO, 400MHz) δ: 1.19(s, 9H, 3×CH 3 ), 7.76 (d, J=8.0Hz, 2H, C 6 h 4 2,6-H), 7.99 (d, J=8.0Hz, 2H, C 6 h 4 3,5-H), 8.08(s, 1H, =CH), 8.29(s, 1H, C 2 h 2 N3 3-H), 9.03(s, 1H, C 2 h 2 N 3 5-H), 13.00 (s, 1H, NH).

Embodiment 3

[0028] 2-{[4-tert-butyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-yl]imino}-5-(2-carboxybenzylidene)-4 - Preparation of thiazolinones

[0029]

[0030] 30ml of acetic acid, 12.0mmol of sodium acetate, 4.0mmol of intermediate 2 and 8.0mmol of o-formylbenzoic acid were heated under reflux for 10h. Cool, pour into saturated brine, filter with suction, wash with water, and recrystallize from ethanol to obtain a yellow solid 2-{[4-tert-butyl-5-(1H-1,2,4-triazol-1-yl)thiazole-2 -yl]imino}-5-(2-carboxybenzylidene)-4-thiazolinone, yield 79%, m.p.258~260°C. 1 H NMR (DMSO, 400MHz) δ: 1.10(s, 9H, 3×CH 3 ), 7.57~7.61 (m, 1H, C 6 h 4 4-H), 7.71~7.72(m, 2H,C 6 h 4 5,6-H), 8.02(d, J=7.6Hz, 1H, C 6 h 4 3-H), 8.29(s, 1H, C 2 h 2 N 3 3-H), 8.34(s, 1H, =CH), 9.01(s, 1H, C 2 h 2 N 3 5-H), 12.88 (s, 1H, NH), 13.39 (s, 1H, COOH).

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Abstract

The invention relates to an application of 2-[5-(azole-1-yl)thiazole-2-imino]-5-benzal-4-thaizolidinone shown by a chemical structural formula I in preparing an influenza virus neuraminidase inhibitor, wherein R1 is selected from nitrogen, C1-C2 alkyl and C3-C4 straight-chain or branched alkyl; X and Y are CH or N; and Z is cyano, C1-C2 carbalkoxy, C3-C4 straight-chain carbalkoxy and C3-C4 branched carbalkoxy or carboxyl.

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 2-[5-(azol-1-yl)thiazole-2-imino]-5-benzylidene-4-thiazolinone Application as an inhibitor of influenza virus neuraminidase (NA). Background technique [0002] Avian influenza virus can cause respiratory or systemic infection of poultry. Highly pathogenic avian influenza virus can directly infect poultry, and can also directly or indirectly infect humans. Highly pathogenic avian influenza viruses are a potential risk factor for influenza in humans and pose a serious threat to human health. After July 2003, H 5 N 1 The unprecedented outbreak of bird flu has spread to 17 countries and regions in Asia, North America, Europe and Africa, causing hundreds of people to be infected and killed, and the direct economic loss is as high as 10 billion US dollars. In March 2003, H 7 N 7 The bird flu spread to the whole...

Claims

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Application Information

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IPC IPC(8): C07D417/14A61P31/16
CPCC07D417/14
Inventor 胡艾希肖梦武叶姣颜晓维刘艾林连雯雯
Owner HUNAN UNIV
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