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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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  • Summary
  • 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 targeted anti-tumor drugs has always been the focus and development of global pharmaceutical companies and governments.

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

Embodiment 1

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

[0038]

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

Embodiment 2

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

[0043]

[0044] 3.4 mmol of 2-amino-6-chlorobenzothiazole, 2 mmol of K 2 CO 3 Add it to a 100ml three-neck bottle as an acid-binding agent, then add 6ml of acetonitrile to dissolve it ultrasonically, absorb 1mmol of the raw material 4-methylbenzyl bromide with a pipette gun, dissolve it in 15ml of acetonitrile, and use a constant pressure burette at a rate of 1 drop / 5s. Drop it into a three-necked bottle at a high speed, heat to reflux for 6-7 hours, and monitor the reaction process by TLC. After the reaction, the reaction liquid was lowered to room temperature, and the solvent was evaporated under reduced pressure. Add 8ml of water and an equal volume of ethyl acetate to extract, repeat a small amount of extraction for 3 times, discard the aqueous layer, and use Na 2 SO 4 dry. The dried organic layer was evaporated to dryness under reduced pressure, made sand and passed through t...

Embodiment 3

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

[0048]

[0049] 3.4 mmol of 2-amino-6-chlorobenzothiazole, 2 mmol of K 2 CO 3 Add it into a 100ml three-necked bottle as an acid-binding agent, then add 6ml of acetonitrile for ultrasonic dissolution, weigh 1mmol of the raw material 4-nitrobenzyl bromide and dissolve it in 15ml of acetonitrile, and drop it into three In the flask, it was heated to reflux for 6-7 hours, and the reaction process was monitored by TLC. After the reaction was over, the reaction solution was lowered to room temperature, and the solvent was evaporated to dryness 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 for 3 times, discard the aqueous layer, and wash the organic layer with Na 2 SO 4 dry. The dried organic ...

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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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