Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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

A technology of methylation and drugs, applied in the field of 6-phenylimidazo[2,1-b]thiazole-3-amide derivatives and their preparation and application, can solve the problems of drug resistance and side effects, Achieve the effect of correct structure, simple reaction and easy access to raw materials

Active Publication Date: 2013-07-17
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1. Preparation of N-(2-morpholinopyridin-5-yl)-2-(6-phenylimidazo[2,1-b]thiazol-3-yl)acetamide (R in formula I 1 =H,R 2 =morpholinyl, compounds 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 completed, add ammonia water (30% by mass) to make the solution alkaline, add dichloromethane to dissolve, and separate the layers to obtain a dichloromethane layer, which is washed with dilute hydrochloric acid to make the solution acidic, and the dichloromethane is concentrated. A white powder was precipitated, filtered and dried to obtain the desired compound, ethyl 6-phenylimidazo[2,1-b]thiazole-3-acetate.

[0038] Step 2): put the above 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, re...

Embodiment 2

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

[0074] Human hepatoma cell HepG-2 and breast cancer cell MDA-MB-231 in logarithmic growth phase were taken (the above cells were purchased from the Cell Bank of the Type Culture Collection, Chinese Academy of Sciences, and the Cell Resource Center of Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences), Take 2×10 5 The density of cells / mL was seeded in 96-well plates, 99 μL / well, at 37°C, 5% CO 2 After culturing in the incubator for 4 hours, the compounds prepared in the example of the present invention were added to each well, so that the final concentrations were 100 μmol / L, 50 μmol / L, 25 μmol / L, 10 μmol / L, 5 μmol / L, 2.5 μmol / L, respectively. 10 concentration gradients of 1 μmol / L, 0.5 μmol / L, 0.25 μmol / L, 0.1 μmol / L. Three duplicate wells were set up for each compound, and negative and positive controls were set at the same time, wherein the negative control was 1% D...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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 improved the cure rate of malignant tumors, but it will bring side effects and drug resistance. . Now with the deepening of the research on cell signaling pathways, people have a deeper understanding of the role of oncogenes and anti-cancer genes in tumor cells, which enables the design of new tumor-specific molecular targets with less side effects. , Anti-tumor drugs with low drug resistance become possible. [0003] Protein tyrosine kinases (PTKs) are extremely important substances in the process of cell signal transduction, and its overexpression will activate its downstream signaling pathways, resultin...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D513/04A61K31/5377A61K31/454A61K31/496A61P35/00A61P39/06A61P29/00A61P31/12A61P9/00A61P37/02A61P15/14A61P1/16
Inventor 蒋宇扬丁怀伟张存龙谭春燕
Owner SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com