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The medical use of 5-(1,2,4-triazol-1-yl)-2-phenylacetamidothiazole

A technology of phenylacetamidothiazole and tert-butyl, applied in the field of compound preparation

Inactive Publication Date: 2016-08-17
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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  • The medical use of 5-(1,2,4-triazol-1-yl)-2-phenylacetamidothiazole
  • The medical use of 5-(1,2,4-triazol-1-yl)-2-phenylacetamidothiazole
  • The medical use of 5-(1,2,4-triazol-1-yl)-2-phenylacetamidothiazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Preparation of 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-phenylacetylaminothiazole:

[0016] 2.0 mmol 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine was dissolved in 20.0 mL dichloromethane, 2.2 mmol phenylacetic acid, 0.03 g 4-dimethyl Aminopyridine (DMAP), 2.2 mmol N, N'-dicyclohexylcarbodiimide (DCC) was added after 0.5 h, stirred at room temperature, reacted for 6.0 h, the reaction solution was neutralized with aqueous sodium bicarbonate solution, stood still, and separated , the organic layer was dried with anhydrous sodium sulfate, filtered, rotary evaporated, and column chromatographed to obtain 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-phenylacetylaminothiazole. The rate is 58.1%, m.p. 177~180℃. 1 H NMR (400 MHz, CDCl 3 ) δ: 1.09 (s, 9H, 3×CH 3 ), 3.85 (s, 2H, CH 2 ), 7.33 (d, J = 7.2 Hz, 2H, C 6 h 5 2,6-H), 7.38-7.45 (m, 3H, C 6 h 5 3,4,5-H), 8.11 (s, 1H, C 2 N 3 h 2 3-H), 8.25 (s, 1H, C 2 N 3 h 2 5-H), 9.03 (s, 1H, NH).

Embodiment 2

[0018] Preparation of 5-(1,2,4-triazol-1-yl)-2-phenylacetamidothiazole (I):

[0019]

[0020] In the formula, R is selected from: C 1 ~C 2 Alkyl, C 3 ~C 4 Straight chain or branched chain alkyl; X 1 、X 2 、X 3 、X 4 、X 5 Respectively selected from: hydrogen, deuterium, C 1 ~C 2 Alkyl, C 3 ~C 4 Straight chain or branched chain alkyl

[0021] According to the method of Example 1, 5-(1,2,4-triazol-1-yl)-2-phenylacetamidothiazole represented by chemical structure I was prepared.

Embodiment 3

[0023] Anti-influenza virus neuraminidase activity of 5-(1,2,4-triazol-1-yl)-2-phenylacetylaminothiazole

[0024] 1. Experimental principle

[0025] The compound MUNANA is a specific substrate of neuraminidase. The metabolites produced under the action of neuraminidase can produce 450 nm fluorescence under the excitation of 360 nm irradiation, and the change of fluorescence intensity can sensitively reflect the activity of neuraminidase . Enzymes are all from A / PR / 8 / 34 (H1N1) virus strain

[0026] 2. Experimental method

[0027] In the enzyme reaction system, a certain concentration of samples and influenza virus neuraminidase NA are suspended in the reaction buffer (pH 6.5), the fluorescent substrate MUNANA is added to start the reaction system, and after incubation at 37°C for 40 minutes, the reaction termination solution is added to terminate the reaction. reaction. Fluorescence intensity values ​​were measured under the parameter conditions of excitation wavelength 360...

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Abstract

The invention relates to an application of 5-(1, 2, 4-triazole-1-yl)-2-phenylacetyl aminothiazole shown as a chemical structural formula I (img file='597988dest_path_image001. TIF' wi='279' he='152' / ) in preparing an influenza virus neuraminidase inhibitor, wherein R is selected from C1-C2 alkyl, C3-C4 straight chain or branch chain alkyl, and X1-X5 are selected from hydrogen, deuterium, C1-C2 alkyl and C3-C4 straight chain or branch chain alkyl.

Description

technical field [0001] The present invention relates to a preparation method of a compound, specifically a preparation method of 5-(1,2,4-triazol-1-yl)-2-phenylacetamidothiazole and its use in the preparation of influenza virus neuraminidase inhibitors application. 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 inhibitors c...

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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