4-tertiary butyl-2-(nitrobenzyl imino) thiazole derivative as well as preparation method and application thereof

A nitrobenzylimino, tert-butyl technology, applied in the field of new compounds and their preparation, can solve the problems of the preparation of thiazole derivatives and the lack of research reports on antitumor activity and the like

Inactive Publication Date: 2010-07-21
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no research report on the preparation and antitumor act

Method used

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  • 4-tertiary butyl-2-(nitrobenzyl imino) thiazole derivative as well as preparation method and application thereof
  • 4-tertiary butyl-2-(nitrobenzyl imino) thiazole derivative as well as preparation method and application thereof
  • 4-tertiary butyl-2-(nitrobenzyl imino) thiazole derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1 Preparation of 5-(2-chlorobenzyl)-4-tert-butyl-2-(3-nitrobenzimino)thiazole

[0015]

[0016] Dissolve 1.0mmol 5-(2-chlorobenzyl)-4-tert-butyl-2-aminothiazole in 10mL toluene, stir at room temperature, add dropwise 1.0mmol 3-nitrobenzaldehyde in toluene, add 0.2mL piperidine , Refluxed water separation reaction 2.0h. Cool, filter with suction, and recrystallize to obtain 5-(2-chlorobenzyl)-4-tert-butyl-2-(3-nitrobenzimino)thiazole, m.p.167~170°C, yield 62.4%, 1 H NMR (400MHz, CDCl 3 )δ: 1.47(s, 9H, 3×CH 3 ), 4.40 (s, 2H, CH 2 ), 7.18~7.42 (m, 4H, 2-ClC 6 h 4 ), 7.66(t, J=8.0Hz, J=8.0Hz, 1H, 3-O 2 NC 6 h 4 5-H), 8.29(d, J=8.0Hz, 1H, 3-O 2 NC 6 h 4 4-H), 8.34(ddd, J=8.0Hz, J=2.4Hz, J=2.0Hz, 1H, 3-O 2 N C 6 h 4 6-H), 8.77(t, J=2.0Hz, J=1.6Hz, 1H, 3-O 2 NC 6 h 4 2-H), 8.89 (s, 1H, N=CH).

Embodiment 2

[0017] Example 2 Preparation of 5-(4-chlorobenzyl)-4-tert-butyl-2-(3-nitrobenzylimino)thiazole

[0018]

[0019] Dissolve 1.0mmol 5-(4-chlorobenzyl)-4-tert-butyl 2-aminothiazole in 5mL benzene, add dropwise 1.0mmol 3-nitrobenzaldehyde in benzene solution, 0.2mL piperidine catalyzed, reflux for 2.5h . Cool, filter with suction, and recrystallize to obtain 5-(4-chlorobenzyl)-4-tert-butyl-2-(3-nitrobenzimino)thiazole, mp126~128°C, yield 76.3%, 1 H NMR (400MHz, CDCl 3 )δ: 1.46(s, 9H, 3×CH 3 ), 4.30 (s, 2H, CH 2 ), 7.16 (d, J=8.4Hz, 2H, 4-ClC 6 h 4 2,6-H), 7.31 (d, J = 8.4Hz, 2H, 4-ClC 6 h 4 3,5-H), 7.66 (t, J=8.0Hz, 1H, 3-O 2 NC 6 h 4 5-H), 8.29(d, J=7.6Hz, 1H, 3-O 2 NC 6 h 4 4-H), 8.35(dd, J=8.0Hz, J=1.2Hz, 1H, 3-O 2 NC 6 h 4 6-H), 8.78(d, J=1.6Hz, 1H, 3-O 2 NC 6 h 4 2-H), 8.90 (s, 1H, N=CH).

Embodiment 3

[0020] Example 3 Preparation of 5-(2,4-dichlorobenzyl)-4-tert-butyl-2-(3-nitrobenzimino)thiazole

[0021]

[0022] Dissolve 1.0mmol 5-(2,4-dichlorobenzyl)-4-tert-butyl-2-aminothiazole in 10mL toluene, stir at room temperature, add dropwise the toluene solution of 1.0mmol 3-nitrobenzaldehyde, add 0.2 mL piperidine, reflux and divide water for 2.5h. Cool, filter with suction, and recrystallize to obtain 5-(2,4-dichlorobenzyl)-4-tert-butyl-2-(3-nitrobenzimino)thiazole, m.p.171~174°C, yield 78.8% , 1 HNMR (400MHz, CDCl 3 )δ: 1.45(s, 9H, 3×CH 3 ), 4.37 (s, 2H, CH 2 ), 7.10 (d, J=8.4Hz, 1H, C 6 h 3 6-H), 7.23 (dd, J=8.4Hz, J=2.0Hz, 1H, C 6 h 3 5-H), 7.44(d, J=2.0Hz, 1H, C 6 h 3 3-H), 7.66(t, J=8.0Hz, J=8.0Hz, 1H, 3-O 2 NC 6 h 4 5-H), 8.29(d, J=8.0Hz, 1H, 3-O 2 NC 6 h 4 4-H), 8.33~8.38(m, 1H, 3-O 2 NC 6 h 4 6-H), 8.78(t, J=1.6Hz, J=1.6Hz, 1H, 3-O 2 NC 6 h 4 2-H), 8.92 (s, 1H, N=CH).

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Abstract

The invention discloses a 4-tertiary butyl-2-(nitrobenzyl imino) thiazole derivative (I) which has the following chemical structural formula, in the formula I, Xi is selected from hydrogen, methoxy group, trifluoro-methyl, ethyoxyl or chlorine; X2 is selected from hydrogen, methoxy group, trifluoro-methyl, ethyoxyl or chlorine; X3 is selected from hydrogen, methoxy group, trifluoro-methyl, ethyoxyl or chlorine; X4 is selected from hydrogen, methoxy group, trifluoro-methyl, ethyoxyl or chlorine; and NO2 is selected from 2-nitryl, 3-nitryl, 4-nitryl or 2,4-dinitryl. The 4-tertiary butyl-2-(nitrobenzyl imino) thiazole derivative (I) has favorable inhibition activity on human cervical cancer cells, human liver cancer cells, human nasopharyngeal carcinoma cells and the like and can be used for preparing medicaments for resisting tumors.

Description

technical field [0001] The present invention relates to novel compounds and their preparation methods and applications, in particular to 4-tert-butyl-2-(nitrobenzimino)thiazole derivatives and their preparation methods and applications. Background technique [0002] Among China's 1.3 billion people, one million people die of cancer every year, about 2 million need treatment, and about 1.3 million die. Cancer has become a major killer of human beings. Thiazole compounds have anticonvulsant, antiviral, antibacterial and insecticidal effects. There is no research report on the preparation and antitumor activity of 4-tert-butyl-2-(nitrobenzimino)thiazole derivatives (I). Contents of the invention [0003] The object of the present invention is to provide a class of 4-tert-butyl-2-(nitrobenzimino)thiazole derivatives represented by the chemical structural formula (I). [0004] [0005] Among them, X in the I formula 1 selected from: hydrogen, methoxy, trifluoromethyl, et...

Claims

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Application Information

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IPC IPC(8): C07D277/42A61K31/426A61P35/00
Inventor 胡艾希玄文静叶姣覃智夏曙向建南李珺姊
Owner HUNAN UNIV
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