Thiazole schiff base containing nitryl, preparation and uses thereof

A technology of thiazole schiff base and schiff base, applied in the field of new compounds and their preparation, can solve the problems of no research report on synthesis and anti-inflammatory activity

Inactive Publication Date: 2009-07-29
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There is no research report on the synthesis and anti-inflammatory activity of nitro-containing thiazole Schiff bases (I, II)

Method used

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  • Thiazole schiff base containing nitryl, preparation and uses thereof
  • Thiazole schiff base containing nitryl, preparation and uses thereof
  • Thiazole schiff base containing nitryl, preparation and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Synthesis of Example 15-(4-chlorobenzyl)-4-tert-butyl-2-(2-nitrobenzimino)thiazole (Ia)

[0015]

[0016] 1mmol 2-nitrobenzaldehyde, 20mL ethanol, slowly add 1mmol 5-(4-chlorobenzyl)-4-tert-butyl-2-aminothiazole ethanol solution dropwise under stirring at room temperature, and reflux for 2h after addition to obtain 5-( 4-Chlorobenzyl)-4-tert-butyl-2-(2-nitrobenzimino)thiazole, yield 72.6%, melting point: 105.1~106.9°C. 1 H NMR (400MHz, CDCl 3 )δ: 1.42(s, 9H, (CH 3 ) 3 ), 4.26 (s, 2H, CH 2 ), 7.14 (d, J=8.0Hz, 2H, C 6 h 4 Cl 3,5-H), 7.26 (d, J=8.0Hz, 2H, C 6 h 4 Cl2, 6-H), 7.62 (t, J=8.0Hz, 1H, C 6 h 3 5-H), 7.76(t, J=8.0Hz, 1H, C 6 h 3 4-H), 8.02(d, J=8.0Hz, 1H, C 6 h 3 6-H), 8.35(dd, J=8.0Hz, J=4.0Hz, 1H, C 6 h 3 3-H), 9.25 (s, 1H, N=CH).

Embodiment 25

[0017] Synthesis of Example 25-(4-chlorophenylbenzyl)-4-tert-butyl-2-(4-nitrobenzyl imino)thiazole (Ib)

[0018]

[0019] Add 1mmol 4-nitrobenzaldehyde and 20mL ethanol to a four-neck flask, slowly add 1mmol ethanol solution of 5-(4-chlorobenzyl)-4-tert-butyl-2-aminothiazole dropwise under stirring at room temperature, and the addition is complete. Refluxing reaction for 2 hours gave 5-(4-chlorophenylbenzyl)-4-tert-butyl-2-(4-nitrobenzimino)thiazole with a yield of 84.7% and a melting point of 127.8-128.2°C. 1 H NMR (400MHz, CDCl 3 )δ: 1.43(s, 9H, (CH 3 ) 3 ), 4.27 (s, 2H, CH 2 ), 7.14 (d, J=8.4Hz, 2H, C 6 h 4 Cl3, 5-H), 7.28 (d, J=8.4Hz, 2H, C 6 h 4 Cl 2,6-H), 8.08(d, J=8.8Hz, 2H, C 6 h 4 NO 2 3,5-H), 8.28(d, J=8.8Hz, 2H, C 6 h 4 NO 2 2,6-H), 8.89 (s, 1H, N=CH).

Embodiment 35

[0020] Synthesis of Example 35-(4-chlorobenzyl)-4-tert-butyl-2-(2-chloro-5-nitrobenzyl imino)thiazole (Ic)

[0021]

[0022] Add 1mmol 2-chloro-5--nitrobenzaldehyde and 20mL ethanol to a four-neck flask, slowly add 1mmol 5-(4-chlorobenzyl)-4-tert-butyl-2-aminothiazole dropwise under stirring at room temperature Ethanol solution, after adding, reflux reaction for 2 hours to get 5-(4-chlorobenzyl)-4-tert-butyl-2-(2-chloro-5-nitrobenzimino)thiazole, yield 42.5%, melting point : 99.2~102.3°C. 1 HNMR (400MHz, CDCl 3 )δ: 1.44(s, 9H, (CH 3 ) 3 ), 4.28 (s, 2H, CH 2 ), 7.14 (d, J=8.4Hz, 2H, C 6 h 4 3,5-H), 7.28 (d, J=8.4Hz, 2H, C 6 h 4 2,6-H), 7.58 (d, J=8.4Hz, 1H, C 6 h 3 3-H), 8.22(dd, J=8.4Hz, J=2.8Hz, 1H, C 6 h 3 4-H), 9.11(d, J=2.8Hz, 1H, C 6 h 3 6-H), 9.24 (s, 1H, N=CH).

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Abstract

The invention discloses thiazole Schiff base (I, II) containing nitryl with a chemical structural formula on the right. A method for preparing the thiazole Schiff base containing the nitryl comprises the steps as follows: nitrobenzene formaldehyde takes reflux reaction with 5-(4-chlorobenzyl)-4-tert-butyl-2-amido thiazole in ethanol to prepare and obtain the thiazole Schiff base [I with chemical name of 5-(4-chlorobenzyl)-4-tert-butyl-2-(nitrobenzyl imino) thiazole] containing the nitryl; or salicylaldehyde takes reflux reaction with 4-(nitrophenyl)-2-amido thiazole in the ethanol to prepare and obtain the thiazole Schiff base [II with chemical name of 4-( nitrophenyl)-2-(2-hydroxy benzyl imino) thiazole] containing the nitryl. The thiazole Schiff base containing the nitryl can be used for preparing anti-inflammatory analgesics.

Description

technical field [0001] The invention relates to a class of novel compounds and their preparation methods and applications, in particular to nitro-containing thiazole Schiff bases and their preparation methods and applications. Background technique [0002] Thiazole compounds have anticonvulsant, antiviral, antibacterial and insecticidal effects. Shao Ling et al. designed and synthesized 4-aryl-5-triazolylthiazole-2-imine compounds, and the results of biological activity assays showed that some compounds had bactericidal activity against P. Michael et al. studied 2-aminothiazole breast cancer drugs; Jiang Fengchao et al. designed and synthesized 4-arylthiazole-2-imine derivatives with inhibitory activity on cell apoptosis. Lin et al. reported that Schiff bases have selective inhibitory effect on COX-2. He Daohang and others studied the synthesis and bactericidal activity of 4-aryl-2-(2-hydroxybenzimino)thiazole; Hu Aixi et al. reported the synthesis and Cyclooxygenase-2 ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/42A61K31/426A61P29/00
Inventor 胡艾希徐江平林焕冰叶姣
Owner HUNAN UNIV
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