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

A kind of technology of fatty amide and thiazole, which is applied in the application field of preparing influenza virus neuraminidase inhibitor

Inactive Publication Date: 2015-07-08
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
  • 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 acetic anhydride, reacted at 50°C for 1.5 h, cooled, poured into ice water and stirred to obtain N -[4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]acetamide, yield 90.6%, m.p. 190~191℃. 1 H NMR (400 MHz, CDCl 3 ) δ : 1.13 (s, 9H, 3 x 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 Preparation of -[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 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℃. 1 H NMR (400 MHz, CDCl 3 ) δ : 1.13 (s, 9H, 3 x 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 - Preparation of [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 was dissolved in 20.0 mL dichloromethane, 2.2 mmol 2-butenoic acid, 0.03 g 4 - Dimethylaminopyridine (DMAP), add 2.2 mmol N, N'-dicyclohexylcarbodiimide (DCC) after 0.5 h, stir at room temperature, react for 6.0 h, the reaction solution is neutralized with aqueous sodium bicarbonate solution, and allowed to stand , layered, the organic layer was dried with anhydrous sodium sulfate, filtered, rotary evaporated, and column chromatography was obtained 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 x 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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PUM

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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 the preparation method of compound, specifically N The preparation method of -[5-(1,2,4-triazol-1-yl)thiazol-2-yl] fatty acid amide and its application in the preparation of influenza virus neuraminidase inhibitors. Background technique [0002] There are two glycoproteins on the surface of influenza virus: hemagglutinin (HA) and neuraminidase (NA). Because NA is relatively conservative in the mutation process of influenza virus, it becomes a very good target for designing and synthesizing anti-influenza drugs. NA catalyzes the cleavage of N-acetylaminoneuraminidase at the terminus of host cell surface glycoproteins, releasing mature influenza virions and preventing the accumulation of new virions. In addition, NA enhances virulence and facilitates virus release from infected host cells by altering the carbohydrate portion of the surface glycoprotein HA, causing or aggravating influenza symptoms. Therefore, NA inhibi...

Claims

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Application Information

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Patent Type & Authority Patents(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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