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N-[4-phenyl-5-(1,2,4-triazole-1-yl)thiazole-2-yl]amide and preparation and application thereof

A thiazole and phenyl technology, applied to N-[4-phenyl-5-(1, can solve the problems of high price and strong irritation, and achieve good anticancer activity

Inactive Publication Date: 2016-03-02
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In this bromination reaction, NBS has high selectivity, but it has a strong irritant and is relatively expensive

Method used

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  • N-[4-phenyl-5-(1,2,4-triazole-1-yl)thiazole-2-yl]amide and preparation and application thereof
  • N-[4-phenyl-5-(1,2,4-triazole-1-yl)thiazole-2-yl]amide and preparation and application thereof
  • N-[4-phenyl-5-(1,2,4-triazole-1-yl)thiazole-2-yl]amide and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of 2-bromo-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanone

[0038] Add 0.1mol of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanone, 3mL of acetic acid, and 0.14mol of sodium bromide into the reaction flask, and stir at 70°C , add 0.3mol30% hydrogen peroxide dropwise, and react for 3.0h; Rate 85.0%. 1 HNMR (CDCl 3 , 400MHz) δ: 8.80 (s, 1H, triazole 5-H), 8.03 (s, 1H, triazole 3-H), 7.71 (s, 1H, CH), 7.66 (d, J=8.0Hz, 1H , C 6 h 3 6-H), 7.52(d, J=8.0Hz, 1H, C 6 h 3 3-H), 7.44~7.42(m, 1H, C 6 h 3 5-H).

Embodiment 2

[0040] Preparation of 2-bromo-1-(2,4-dichloro-5-fluorophenyl-2-(1,2,4-triazol-1-yl)ethanone

[0041] 0.1mol 1-(2,4-dichloro-5-fluorophenyl)-2-(1,2,4-triazol-1-yl)ethanone, 3mL acetic acid, 0.14mol sodium bromide were added to the reaction flask, 70 Stir at ℃, add 0.3mol30% hydrogen peroxide dropwise, react for 3.0h; get 2-bromo-1-(2,4-dichloro-5-fluorophenyl)-2-(1,2,4-triazole-1 -base) ethyl ketone, yield 88.0%. 1 HNMR (CDCl 3 , 400MHz) δ: 8.76 (s, 1H, triazole 5-H), 8.03 (s, 1H, triazole 3-H), 7.73 (s, 1H, CH), 7.59~7.54 (m, 2H, C6H23, 6-H).

Embodiment 3

[0043] Preparation of 4-(2,4-dichloro-5-fluorophenyl)-5-(1,2,4-triazol-1-yl)thiazol-2-amine

[0044] 1mmol 2-bromo-1-(2,4-dichloro-5-fluorophenyl)-2-(1,2,4-triazol-1-yl)ethanone, 20mL ethanol, reflux, add 1mmo l Thiourea, monitored by TLC, reacted for 10 minutes, cooled to 40°C, added dropwise dilute ammonia water to pH=7-8, and filtered with suction to obtain light yellow solid 4-(2,4-dichloro-5-fluorophenyl)-5- (1,2,4-Triazol-1-yl)thiazol-2-amine, yield 80.3%, m.p.251-253°C. 1 HNMR (CDCl 3 , 400MHz) δ: 8.02 (s, 1H, triazole 5-H), 7.94 (s, 1H, triazole 3-H), 7.49~7.47 (m, 1H, phenyl 3-H), 7.26~7.25 ( m, 1H, phenyl 6-H), 5.78 (s, 2H, NH 2 ).

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Abstract

The invention relates to N-[4-phenyl-5-(1,2,4-triazole-1-yl)thiazole-2-yl]amide shown in a chemical structural formula I (please see the formula in the specification), wherein X<1> and X<3> are selected from chlorine, bromine, fluorine and iodine, X<4> is selected from hydrogen, deuterium, methyl, ethyl, chlorine, bromine, fluorine and iodine, X<2> and X<5> are selected from hydrogen, deuterium, methyl and ethyl, R is selected from hydrogen and methyl, n is selected from 0,1,2 and 3, and Y is selected from hydrogen, C1-C2 alkyl, C3-C11 straight-chain alkyl or branch-chain alkyl, C1-C2 halogenation alkyl or dihalogenation alkyl, C3-C5 halogenation straight-chain alkyl or halogenation branch-chain alkyl and phenyl. The application of the N-[4-phenyl-5-(1,2,4-triazole-1-yl)thiazole-2-yl]amide in preparation of anti-cancer drugs or neuraminidase inhibitors for Hela cells is achieved.

Description

technical field [0001] The present invention relates to the preparation and application of novel compounds, specifically the preparation and application of N-[4-phenyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]amide. Background technique [0002] 2-Bromo-1-phenyl-2-(1,2,4-triazol-1-yl)ethanone is the preparation of 4-phenyl-5-(1,2,4-triazol-1-yl) - The key intermediate of 1,3-thiazol-2-amine and its derivatives. The preparation of 2-bromo-1-phenyl-2-(1,2,4-triazol-1-yl)ethanone and its use in the synthesis of thiazole derivatives has been described [J.Organomet.Chem. 2006, 691: 2686; Synth.Commun.2007, 37: 199; HeteroatChem 2007, 18: 55; Chemical Journal of Higher Schools, 2007, 28: 270-273; Organic Chemistry, 2012, 32: 1715-1718]. Fang Jianxin et al. describe bromination of 1-phenyl-2-(1,2,4-triazol-1-yl)ethanone with molecular bromine in acetic acid to obtain 2-bromo-1-phenyl-2-(1 , 2,4-triazol-1-yl) ethanone; The preparation reaction is as follows: [0003] [0004] In th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A61K31/427A61P35/00A61P31/16
Inventor 胡艾希张明明丁娜叶姣颜晓维向建南
Owner HUNAN UNIV
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