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Medical application of N-{5-(1,2,4-triazole-1-yl) thiazole-2-yl} fatty acid amide

The technology of a kind of fatty amide, thiazole is applied in the application field in the preparation of influenza virus neuraminidase inhibitor

Inactive Publication Date: 2014-04-09
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, studies have found that some virus strains are resistant to Oseltamivir, so there is an urgent need to study new anti-influenza A virus drugs

Method used

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  • Medical application of N-{5-(1,2,4-triazole-1-yl) thiazole-2-yl} fatty acid amide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0007] N Preparation of -[4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]acetamide

[0008] 2 mmol 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine, 6.0 mL of acetic anhydride, reacted at 50°C for 1.5 h, after cooling, poured into ice water and stirred to obtain N -[4-tert-Butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]acetamide, the yield is 90.6%, m.p. 190~191℃. 1 H NMR (400 MHz, CDCl 3 ) δ : 1.13 (s, 9H, 3×CH 3 ), 2.29 (s, 3H, CH 3 ), 8.12 (s, 1H, C 2 N 3 H 2 3-H), 8.28 (s, 1H, C 2 N 3 H 2 5-H), 9.16 (s, 1H, NH).

Embodiment 2

[0010] N -[4-tert-Butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]propionamide

[0011] According to the method of Example 1, 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine was reacted with propionic anhydride for 0.5 h to obtain N -[4-tert-Butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]propionamide, yield 87.2%, m.p. 159~161°C. 1 H NMR (400 MHz, CDCl 3 ) δ : 1.13 (s, 9H, 3×CH 3 ), 1.28 (t, J = 7.6 Hz, 3H, CH 3 ), 2.54 (q, J = 7.6 Hz, 2H, CH 2 ), 8.15 (s, 1H, C 2 N 3 H 2 3-H), 8.31 (s, 1H, C 2 N 3 H 2 5-H), 9.49 (s, 1H, NH).

Embodiment 3

[0013] N -[4-tert-Butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]-2-butenamide

[0014] 2 mmol 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine dissolved in 20.0 mL dichloromethane, add 2.2 mmol 2-butenoic acid, 0.03 g 4 -Dimethylaminopyridine (DMAP), after 0.5 h, add 2.2 mmol N,N'-dicyclohexylcarbodiimide (DCC), stir at room temperature, react for 6.0 h, the reaction solution is neutralized with sodium bicarbonate aqueous solution, and stand still , Separate layers, dry the organic layer with anhydrous sodium sulfate, filter, rotary steam, and column chromatography to obtain N -[4-tert-Butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]-2-butenamide, yield 35.8%, m.p. 205~208℃. 1 H NMR (400 MHz, CDCl 3 ) δ : 1.15 (s, 9H, 3×CH 3 ), 1.98 (dd, J = 7.0 Hz, J = 1.6 Hz, 3H, CH 3 ), 5.99 (dd, J = 14.2 Hz, J = 1.6 Hz, 1H, 3'-H), 7.13-7.19 (m, 1H, 2'-H), 8.12 (s, 1H, C 2 N 3 H 2 3-H), 8.26 (s, 1H, C 2 N 3 H 2 5-H), 8.92 (s, 1H, NH).

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Abstract

The invention relates to application of N-{5-(1,2,4-triazole-1-yl) thiazole-2-yl} fatty acid amide in preparing an influenza virus neuraminidase inhibitor. The N-{5-(1,2,4-triazole-1-yl) thiazole-2-yl} fatty acid amide has the chemical structural formula shown as I, wherein in the formula I, R is selected from C1 to C2 alkyls, C3 to C4 straight chains or branched alkyls; R1 is selected from C1 to C2 alkyls, C3 to C11 straight chains or branched alkyls, C12 to C17 straight chains or branched alkyls, vinyls, allyls or C4 to C17 alkyls containing dual keys or three keys.

Description

Technical field [0001] The present invention relates to a preparation method of a compound, specifically N Preparation method of [5-(1,2,4-triazol-1-yl)thiazol-2-yl] fatty amide and its application in preparing influenza virus neuraminidase inhibitor. Background technique [0002] There are two glycoproteins on the surface of influenza viruses: hemagglutinin (HA) and neuraminidase (NA). Because NA is relatively conservative in the mutation process of influenza virus, it becomes a very good target for the design and synthesis of anti-influenza drugs. NA can catalyze the cleavage of N-acetylaminoneuraminidase at the end of glycoprotein on the surface of host cells, release mature influenza virions, and prevent the aggregation of new virions. In addition, NA enhances toxicity by changing the carbohydrate portion of the surface glycoprotein HA, and promotes the release of virus from infected host cells, causing or aggravating influenza symptoms. Therefore, NA inhibitors can inhibit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/427A61P31/16
Inventor 陈平孙晓潇陈洁
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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