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6-phenylimidazol[2, 1-b]thiazole-3-amide derivative, its preparation method and application

A fluorophenyl and methyl technology, which is applied to 6-phenylimidazo[2,1-b]thiazole-3-amide derivatives and their preparation and application fields, can solve side effects, generate drug resistance, etc. problem, to achieve the effect of simple reaction, correct structure, and easy availability of raw materials

Active Publication Date: 2014-12-17
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Tumor is a common and frequently-occurring disease. Cancer has seriously threatened human health and life. The combination of traditional surgery, chemotherapy and radiotherapy has successfully improved the cure rate of malignant tumors, but it will bring side effects and drug resistance.

Method used

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  • 6-phenylimidazol[2, 1-b]thiazole-3-amide derivative, its preparation method and application
  • 6-phenylimidazol[2, 1-b]thiazole-3-amide derivative, its preparation method and application
  • 6-phenylimidazol[2, 1-b]thiazole-3-amide derivative, its preparation method and application

Examples

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Effect test

Embodiment 1

[0036] Example 1. Preparation of N-(2-morpholinylpyridin-5-yl)-2-(6-phenylimidazo[2,1-b]thiazol-3-yl)acetamide (R in formula I 1 =H, R 2 =morpholinyl, compound with n=0)

[0037] Step 1): Add 4.7 g (0.025 mol) of 2-aminothiazole-4-ethyl acetate, 5.0 g (0.025 mol) of α-bromoacetophenone, and 50 ml of acetone into a 100 ml three-necked flask, and reflux for 8 hours. After the reaction is complete, add ammonia water (mass concentration 30%) to make the solution alkaline, add dichloromethane to dissolve, separate the liquids to obtain a dichloromethane layer, wash with dilute hydrochloric acid to make the solution acidic, concentrate the dichloromethane, A white powder precipitated, filtered, and dried to obtain the desired compound 6-phenylimidazo[2,1-b]thiazole-3-ethyl acetate.

[0038] Step 2): Put the above ethyl 6-phenylimidazo[2,1-b]thiazole-3-ethyl acetate into a 250ml round bottom flask, add ethanol-water-sodium hydroxide solution (7:3, v / v; 1.5mol / L) 50ml, refluxed for 0.5 h...

Embodiment 2

[0073] Example 2. Screening of cell proliferation inhibitory activity by MTT method

[0074] Take the human liver cancer cell HepG-2 and breast cancer cell MDA-MB-231 in the logarithmic growth phase (the above cells were purchased from the Cell Bank of the Type Culture Collection Committee of the Chinese Academy of Sciences, and the Cell Resource Center of the Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences), 2×10 5 Inoculated into a 96-well plate at a density of pieces / mL, 99μL / well, at 37℃, 5% CO 2 After culturing in the incubator for 4 hours, add the compound prepared in the embodiment of the present invention to each well to make the final concentration 100μmol / L, 50μmol / L, 25μmol / L, 10μmol / L, 5μmol / L, 2.5μmol / L, 10 concentration gradients of 1μmol / L, 0.5μmol / L, 0.25μmol / L, 0.1μmol / L. There are three multiple wells for each compound, and negative and positive controls are set at the same time. The negative control is a 1% DMSO solution by volume. Aft...

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Abstract

The invention discloses a 6-phenylimidazol[2, 1-b]thiazole-3-amide derivative, its preparation method and application. The structural formula of the compound is shown as formula I, wherein R1 is H, or one or more of the following mono-substituted or multi-substituted groups on a benzene ring: fluorine, chlorine, bromine, methyl, methoxyl, hydroxyl, nitro, amino, trifluoromethyl and cyano; R2 is hydrogen, fluorine, chlorine, bromine, methyl, methoxyl, hydroxyl, mercapto, amino, methylamino, ethylamino, morpholine, piperazine, methyl piperazine, ethyl piperazine, benzyl piperazine, p-methoxylbenzyl piperazine or p-chlorobenzyl piperazine; and n is 0 or 1 or 2. The raw materials for preparation of the derivative are easily available, the reaction is simple, and the synthesis steps are simple and are easy to operate. The compound provided in the invention has good anti-tumor activity, and has important practical value and application prospects in the field of antitumor medicine preparation. (Formula I).

Description

Technical field [0001] The invention relates to a 6-phenylimidazo[2,1-b]thiazole-3-amide derivative and a preparation method and application thereof. Background technique [0002] Tumor is a common and frequently-occurring disease. Cancer has seriously threatened human health and life. The combination of traditional surgery, chemotherapy and radiotherapy has successfully increased the cure rate of malignant tumors, but it will bring side effects and drug resistance. . Now with the deepening of research on cell signal transduction pathways, people are getting more and more in-depth understanding of the role of oncogenes and anti-oncogenes in tumor cells, so that new tumor-specific molecular targets can be designed with fewer side effects. , Anti-tumor drugs with low drug resistance become possible. [0003] Protein tyrosine kinases (PTK) is an extremely important substance in the process of cell signal transduction. Its overexpression will activate its downstream signal pathways, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61P35/00A61K31/496C07D513/04A61P1/16A61P29/00A61P9/00A61P31/12A61K31/5377A61P39/06A61P15/14A61P37/02A61K31/454
Inventor 蒋宇扬丁怀伟张存龙谭春燕
Owner SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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