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N-(5-benzyl thiazole-2-yl)benzamide, and pharmaceutical applications thereof

A technology of benzylthiazole and benzamide, which is applied in pharmaceutical formulations, medical preparations containing active ingredients, organic chemistry, etc.

Inactive Publication Date: 2015-07-15
HUNAN UNIV
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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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  • N-(5-benzyl thiazole-2-yl)benzamide, and pharmaceutical applications thereof
  • N-(5-benzyl thiazole-2-yl)benzamide, and pharmaceutical applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Preparation of N-[4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-yl]-2,6-difluorobenzamide

[0014] 1.5mmol 4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-amine, 1.6mmol 2,6-difluorobenzoic acid and 40mL dichloromethane, stirred at room temperature, added 0.15mmol 4-dimethylamino Pyridine, stirred for 0.5h, added 1.6mmol N,N'-dicyclohexylcarbodiimide, and TLC monitored the reaction. After the reaction was completed, the column was passed to obtain N-[4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-yl]-2,6-difluorobenzamide with a yield of 78.1%. m.p.133~135℃. 1 H NMR (CDCl 3 , 400MHz), δ: 1.32 (s, 9H, 3×CH 3 ), 4.29 (s, 2H, CH 2 ), 7.00~7.51 (m, 6H, 2×C 6 h 3 ), 9.40 (br, 1H, NHCO).

Embodiment 2

[0016] Preparation of N-[4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-yl]-2-chlorobenzamide

[0017] 1.5mmol 4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-amine, 1.6mmol 2-chlorobenzoic acid and 40mL dichloromethane, stirred at room temperature, added 0.15mmol 4-dimethylaminopyridine, stirred 0.5h, 1.6mmol N,N'-dicyclohexylcarbodiimide was added, and the reaction was monitored by TLC. After the reaction was completed, the column was passed to obtain N-[4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-yl]-2-chlorobenzamide with a yield of 78.3%, m.p.148~ 150°C. 1 H NMR (CDCl 3 , 400MHz), δ: 1.34 (s, 9H, 3×CH 3 ), 4.30 (s, 2H, CH 2 ), 7.08 (d, J=8.4Hz, 1H, C 6h 3 6-H), 7.18 (dd, J=8.4Hz, J=2.0Hz, 1H, C 6 h 3 5-H), 7.39~7.81 (m, 5H, ClC 6 h 3 3-H,C 6 h 4 ), 9.50 (br, 1H, NHCO).

Embodiment 3

[0019] Preparation of N-[4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-yl]-4-chlorobenzamide

[0020] 1.5mmol 4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-amine, 1.6mmol 4-chlorobenzoic acid and 40mL dichloromethane, stirred at room temperature, added 0.15mmol 4-dimethylaminopyridine, stirred 0.5h, 1.6mmol N,N'-dicyclohexylcarbodiimide was added, and the reaction was monitored by TLC. After the reaction was completed, the column was passed to obtain N-[4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-yl]-4-chlorobenzamide, yield 74.5%, m.p.137~ 140°C. 1 H NMR (CDCl 3 , 400MHz), δ: 1.36 (s, 9H, 3×CH 3 ), 4.29 (s, 2H, CH 2 ), 7.06 (d, J=8.4Hz, 1H, C 6 h 3 6-H), 7.18 (dd, J=8.4Hz, J=2.4Hz, 1H, C 6 h 3 5-H), 7.41 (d, J=2.4Hz, 1H, C 6 h 3 3-H), 7.49 (d, J=8.8Hz, 2H, C 6 h 4 3,5-H), 7.89 (d,, J=8.8Hz, 2H, C 6 h 4 2,6-H), 9.57 (br,1H, NHCO).

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Abstract

The invention relates to applications of N-(5-benzyl thiazole-2-yl)benzamide represented by chemical structural formula I in preparing neuraminidase inhibitors. According to the chemical structural formula I, R is selected from C1-C2 alkyl, C3-C4 linear alkyl or branched alkyl; Y1 is selected from hydrogen, deuterium, methyl, ethyl, fluorine, chlorine, and bromine; Y2 and Y4 are selected from hydrogen, deuterium, methyl, ethyl, fluorine, chlorine, and bromine; Y3 is selected from hydrogen, deuterium, methyl, ethyl, fluorine, chlorine, and bromine; R1 and R5 are selected from hydrogen, deuterium, methyl, ethyl, methoxyl, ethyoxyl, fluorine, chlorine, bromine, nitryl, trifluoromethyl, or trifluoromethoxy; R2 and R4 are selected from hydrogen, deuterium, methyl, ethyl, hydroxyl, methoxyl, ethyoxyl, fluorine, chlorine, bromine, nitryl, trifluoromethyl, or trifluoromethoxy; R3 is selected from hydrogen, deuterium, methyl, ethyl, hydroxyl, methoxyl, ethyoxyl, fluorine, chlorine, bromine, nitryl, trifluoromethyl, or trifluoromethoxy.

Description

technical field [0001] The present invention relates to a new application of the compound, specifically the application of N-(5-benzylthiazol-2-yl)benzamide in the preparation 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, releasing mature influenza virions and preventing the accumulation of new virions. In a...

Claims

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Application Information

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IPC IPC(8): A61K31/426A61P31/16C07D277/46
Inventor 胡艾希伍智林申坤彭俊梅刘艾琳连雯雯
Owner HUNAN UNIV
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