6-chloro-2-aminobenzothiazole derivative as well as preparation method and application thereof

An aminobenzene and thiazole technology, which is applied in the field of 6-chloro-2-aminobenzothiazole derivatives, can solve problems such as high toxicity, and achieve the effects of simple preparation method, cheap raw materials and good inhibitory activity

Active Publication Date: 2017-05-31
WENZHOU MEDICAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the shortcomings of existing anti-tumor drugs such as high toxicity and easy drug resistance, the development of

Method used

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  • 6-chloro-2-aminobenzothiazole derivative as well as preparation method and application thereof
  • 6-chloro-2-aminobenzothiazole derivative as well as preparation method and application thereof
  • 6-chloro-2-aminobenzothiazole derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0037] Example 1 Preparation of 6-chloro-N-(3-fluorobenzyl)benzo[d]thiazol-2-amine (K1):

[0038]

[0039] 3.4mmol of 2-amino-6-chlorobenzothiazole, 2mmol of K 2 CO 3 Add it as an acid binding agent to a 100ml three-necked flask, and then add 6ml of acetonitrile to dissolve it ultrasonically, use a pipette to suck up the raw material 1mmol 3-fluorobenzyl bromide, dissolve it in 15ml of acetonitrile, and use a constant pressure burette to drip at a rate of 1 drop / 5s Put it into a three-necked flask and heat to reflux for 6-7 hours. The reaction process is monitored by TLC. After the reaction, the reaction solution was reduced to room temperature, and the solvent was evaporated under reduced pressure. Add 8ml of water and an equal volume of ethyl acetate for extraction, repeat the extraction for 3 times in small quantities, discard the water layer, and use Na for the organic layer 2 SO 4 dry. The dried organic layer is evaporated to dryness under reduced pressure, and sand is made...

Example Embodiment

[0042] Example 2 Preparation of 6-chloro-N-(4-methylbenzyl)benzo[d]thiazol-2-amine (K2)

[0043]

[0044] 3.4mmol of 2-amino-6-chlorobenzothiazole, 2mmol of K 2 CO 3 Add it as an acid binding agent to a 100ml three-necked flask, and then add 6ml of acetonitrile to ultrasonically dissolve it. Use a pipette to draw 1mmol of raw material 4-methylbenzyl bromide and dissolve it in 15ml of acetonitrile. Use a constant pressure burette to take 1 drop / 5s Drop into a three-necked flask at a rate and heat to reflux for 6-7 hours. The reaction process is monitored by TLC. After the reaction, the reaction solution was reduced to room temperature, and the solvent was evaporated under reduced pressure. Add 8ml of water and an equal volume of ethyl acetate for extraction, repeat the extraction for 3 times in small quantities, discard the water layer, and use Na for the organic layer 2 SO 4 dry. The dried organic layer is evaporated to dryness under reduced pressure, and sand is made to pass th...

Example Embodiment

[0047] Example 3 Preparation of 6-chloro-N-(4-nitrobenzyl)benzo[d]thiazol-2-amine (K3)

[0048]

[0049] 3.4mmol of 2-amino-6-chlorobenzothiazole, 2mmol of K 2 CO 3 Add it as an acid binding agent to a 100ml three-necked flask, and then add 6ml of acetonitrile to dissolve ultrasonically, weigh out 1mmol of raw material 4-nitrobenzyl bromide and dissolve it in 15ml of acetonitrile, and use a constant pressure burette to drip into three at a rate of 1 drop / 5s In a neck flask, heat to reflux for 6-7h, and the reaction process was monitored by TLC. After the reaction is over, the reaction solution is reduced to room temperature, and the solvent is evaporated under reduced pressure. Add 8ml of water and an equal volume of ethyl acetate for extraction. Insoluble matter appears. Filter with suction. Discard the solid. Wash the solid with a small amount of water and ethyl acetate. Repeat the extraction 3 times. Discard the water layer and use Na for the organic layer. 2 SO 4 dry. The dr...

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Abstract

The invention discloses a 6-chloro-2-aminobenzothiazole derivative as well as a preparation method and application thereof. The structure of the 6-chloro-2-aminobenzothiazole derivative is shown in a formula (I), wherein R is selected from substituted or unsubstituted benzyl, C2-C5 alkyl, substituted or unsubstituted benzolyl or C1-C6 alkyl acyl; and the benzyl or a substituent group on the benzyl is independently selected from C1-C4 alkyl, C1-C4 alkoxy, nitryl or halogen. The 6-chloro-2-aminobenzothiazole derivative has better inhibitory activity on tumor cells highly expressed by EGFRWT, provides a new strategy and a new thought for tumor treatment and provides a new direction and a new thought for research and development of anti-tumor drugs. (The formula (I) is described in the specification).

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular, the invention relates to a compound with good anti-EGFR WT 6-chloro-2-aminobenzothiazole derivatives with high expression of tumor cell activity. In addition, the present invention also relates to the preparation method of this type of compound and its anti-EGFR WT The activity of highly expressed tumor cells A549 and A431. Background technique [0002] Malignant tumor is a common and frequently-occurring disease that seriously threatens human health. It is characterized by abnormal proliferation of cells or mutant cells. At present, the death caused by malignant tumors accounts for the second place in the death rate of all diseases, second only to cardiovascular and cerebrovascular diseases. Due to the shortcomings of existing anti-tumor drugs such as high toxicity and easy drug resistance, the development of targeted anti-tumor drugs has always been an area of ​​focus and de...

Claims

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Application Information

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IPC IPC(8): C07D277/82A61K31/428A61P35/00
CPCC07D277/82
Inventor 叶发青郭平张再葵罗露潘雅倩谢自新林丹张园王学宝张金三郭强
Owner WENZHOU MEDICAL UNIV
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