2-(2-Benzylhydrazonyl)-5-(1,2,4-triazole-1-yl)thiazole and its preparation and application

A technology of nitrobenzylhydrazine and hydroxybenzylhydrazine, which is applied in the field of application in the preparation of influenza virus neuraminidase inhibitors

Inactive Publication Date: 2017-03-08
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, so there is an urgent need to study new anti-influenza A virus drugs

Method used

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  • 2-(2-Benzylhydrazonyl)-5-(1,2,4-triazole-1-yl)thiazole and its preparation and application
  • 2-(2-Benzylhydrazonyl)-5-(1,2,4-triazole-1-yl)thiazole and its preparation and application
  • 2-(2-Benzylhydrazonyl)-5-(1,2,4-triazole-1-yl)thiazole and its preparation and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-1-bromo-2-butanone

[0020]0.02mol3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone, 4.0mL glacial acetic acid, 40.0mL carbon tetrachloride, 0.022mol sodium bromide, 6.0 Add 1.2 mL of sulfuric acid, add 4.6 mL of 30% hydrogen peroxide dropwise at 65°C, and react for 2.5 hours; add 20.0 mL of aqueous sodium bicarbonate solution, stir until no bubbles emerge, separate the organic layer, extract with dichloromethane, and combine The organic layer was washed with saturated sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed to obtain a light yellow liquid of 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-1-bromo-2-butanone; the light yellow liquid was directly used in the next reaction.

Embodiment 2

[0022] Preparation of 2-[2-(4-methylbenzylhydrazono)]-4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazole and its hydrobromide

[0023] 5mmol thiosemicarbazide was dissolved in 20.0mL mixed solvent (V 乙醇 :V 水 =1:3), reflux, add 5mmol of 4-methylbenzaldehyde ethanol solution dropwise, react for 0.5h, the reaction solution is cooled to precipitate a solid, filtered, dried, and recrystallized from ethanol to obtain 4-methylbenzylhydrazonothioamide , yield 82.5%, m.p.165~167℃.

[0024] 5mmol of 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-1-bromo-2-butanone was dissolved in 20.0mL of ethanol, and 5mmol of 4-methylbenzylhydrazonosulfur was added Substituted amide, reflux, reacted for 0.5h, the reaction solution was cooled to precipitate a solid, filtered to obtain 2-[2-(4-methylbenzylhydrazono)]-4-tert-butyl-5-(1,2,4- Triazol-1-yl)thiazole hydrobromide, yield 76.6%, m.p.221~223℃. 1 H NMR (400MHz, CDCl 3 ) δ: 1.29 (s, 9H, 3 × CH 3 ), 2.41 (s, 3H, CH 3 ), 7.25 (d, J=8.0Hz, 2H, C 6 h 4 3,5-H)...

Embodiment 3

[0027] Preparation of 2-[2-(4-fluorobenzylhydrazono)]-4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazole and its hydrobromide

[0028] 5mmol thiosemicarbazide was dissolved in 20.0mL mixed solvent (V 乙醇 :V 水 =1:3), reflux, add 5mmol of 4-fluorobenzaldehyde ethanol solution dropwise, react for 1.0h, the reaction liquid is cooled to precipitate solid, filtered, dried, ethanol recrystallized to obtain 4-fluorobenzylhydrazonothioamide, yield The rate is 93.1%, m.p.195~198℃.

[0029] Dissolve 5mmol of 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-1-bromo-2-butanone in 20.0mL of ethanol, add 5mmol of 4-fluorobenzylhydrazonothio Amide, reflux, react for 0.2h, the reaction solution is cooled to precipitate a solid, filtered to obtain 2-[2-(4-fluorobenzylhydrazono)]-4-tert-butyl-5-(1,2,4-triazole -1-yl) thiazole hydrobromide, yield 86.8%, m.p.208~211℃. 1 H NMR (400MHz, CDCl 3 ) δ: 1.30 (s, 9H, 3×CH 3 ), 7.14 (t, J=8.8Hz, 2H, C 6 h 4 3,5-H), 7.69 (dd, J=8.8Hz, J=1.6Hz, 2H, C 6 h 4 2,6-H), 8.18...

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Abstract

The invention relates to 2-(2-benzylidene hydrazino)-5-(1,2,4-triazole-1-yl)thiazole represented by chemical structural formula I, or salts thereof. According to the chemical structural formula I, R is selected from hydrogen, deuterium, C1-C2 alkyl, and C3-C4 linear alkyl or branched alkyl; and X1-X5 are selected from hydrogen, deuterium, C1-C2 alkyl, hydroxyl, methoxyl, ethyoxyl, fluorine, chlorine, bromine, and nitryl. The invention also discloses applications of 2-(2-benzylidene hydrazino)-5-(1,2,4-triazole-1-yl)thiazole in preparing influenza neuraminidase inhibitors.

Description

technical field [0001] The present invention relates to the preparation and application of a class of novel compounds, specifically the preparation of 2-(2-benzylhydrazono)-5-(1,2,4-triazol-1-yl)thiazole and its use in the preparation of influenza virus Use of 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 is a mushroom cloud-shaped envelope glycoprotein, composed of 453-466 amino acids, its structure is divided into head and neck, the head contains enzymes, has antigenicity, and the neck has a hydrophobic region, making it easy to insert into the double layer in the lipid membrane. NA catalyzes the cleavage of N-acetylaminoneuraminidase at the terminus of host cell surface glycoproteins, relea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04A61P31/16
CPCC07D417/04
Inventor 胡艾希叶姣孙晓潇刘艾琳连雯雯
Owner HUNAN UNIV
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