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

Preparation of novel fluoro thiazole hydrazone compounds and application thereof to anti-tumor medicine

A technology of fluorothiazole hydrazone and substituted thiazole hydrazone, which is applied in the fields of antineoplastic drugs, drug combinations, organic chemistry, etc., can solve the problem of no fluorothiazole hydrazone compounds, etc., and achieve strong inhibitory activity, good application prospects, and good anti-tumor effect. The effect of tumor activity

Inactive Publication Date: 2017-05-31
INST OF OCEANOLOGY - CHINESE ACAD OF SCI
View PDF1 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention couples active groups of thiazole and hydrazone compounds to design and synthesize fluorothiazole hydrazone compounds. In the prior art, there is no report on the fluorothiazole hydrazone compounds provided by the present invention and the pharmaceutical composition thereof as active ingredients. There is no report on the application of such derivatives or their pharmaceutical compositions in the preparation or treatment of drugs for diseases such as tumors caused by various factors

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
  • Preparation of novel fluoro thiazole hydrazone compounds and application thereof to anti-tumor medicine
  • Preparation of novel fluoro thiazole hydrazone compounds and application thereof to anti-tumor medicine
  • Preparation of novel fluoro thiazole hydrazone compounds and application thereof to anti-tumor medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: 4-(3-bromophenyl)-2-(2-(3,4-difluorobenzylidene)hydrazino)thiazole (4-(3-bromophenyl)-2-(2-( 3,4-difluorobenzylidene) hydrazinyl) thiazole, compound I) preparation

[0027] (1) Weigh 10mmol 3,4-difluorobenzaldehyde (3.07g) and 11mmol thiosemicarbazide (2.165g) into a 500mL reaction flask, add 30mL ethanol (95%) and stir evenly, then add 1mL glacial acetic acid dropwise , then reflux and stir at 65-70°C for about 10 hours, evaporate most of the ethanol under reduced pressure, add 20 ml of ice water, filter to obtain a precipitate, wash the precipitate with ice water (30 mL for three times), and recrystallize from ethanol to obtain the intermediate 3,4-difluoro Benzylidenethiosemicarbazide (compound a).

[0028] (2) Weigh 1mmol of intermediate 3,4-difluorobenzylidene thiosemicarbazide (215mg) and 4mmol of anhydrous sodium acetate into a 250mL reaction bottle, add 20mL of absolute ethanol, and then add 1mmol of 2,3' -Dibromoacetophenone (278mg), then heated to...

Embodiment 2

[0029]Example 2: 2-(2-(3,4-difluorobenzylidene)hydrazino)-4-(3,4-difluorophenyl)thiazole (2-(2-(3,4-difluorobenzylidene )hydrazinyl)-4-(3,4-difluorophenyl)thiazole, compound II)

[0030] The preparation method of Compound II is similar to that of Compound I, except that the raw material 2,3'-dibromoacetophenone is replaced by 3',4'-difluoro-2-bromoacetophenone from Example 1 Ketone, compound II was prepared, gray solid, yield 82%, 1 H-NMR (500MHz, DMSO- d6 )δ:12.26(1H,s),7.95(1H,s),7.78(1H,m),7.58-7.65(2H,overlap),7.38-7.45(4H,overlap); 13 C-NMR (125MHz, DMSO- d6 )δ: 168.6, 151.1, 150.2, 149.2, 148.8, 148.3, 139.5, 138.7, 132.7, 132.6, 123.7, 122.6, 118.4, 118.1, 114.8, 114.6, 105.4; ESIMS: m / z352[M+H] + HRESIMS: calc for C16H9N3F4S[M+H] + 352.0526,found 352.0452.

Embodiment 3

[0031] Example 3: 2-(2-(3,4-difluorobenzylidene)hydrazino)-4-(4-(trifluoromethyl)phenyl)thiazole (2-(2-(3,4 -difluorobenzylidene)hydrazinyl)-4-(4-(trifluoromethyl)phenyl)thiazole, compound III)

[0032] The preparation method of compound III is similar to the preparation method of compound I, and its difference from Example 1 is that the raw material 2,3'-dibromoacetophenone is replaced by 4'-trifluoromethyl-2-bromoacetophenone , prepared compound III, gray solid, yield 78%, 1 H-NMR (500MHz, DMSO- d6 )δ:12.31(1H,s),8.01(2H,d,J=8.0Hz),7.96(1H,s),7.69(2H,d,J=8.0Hz),7.61(1H,dd,J=9.5 ,9.5Hz),7.50(1H,s),7.38-7.45(2H,overlap); 13 C-NMR (125MHz, DMSO- d6 )δ: 168.8, 151.2, 149.5, 149.3, 139.5, 138.7, 132.6, 128.0, 127.9, 126.4, 125.9, 123.7, 118.3, 114.9, 107.0; ESIMS: m / z 384 [M+H] + HRESIMS:calc forC17H10N3F5S[M+H] + 384.0588,found 384.0535.

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 relates to preparation of novel fluoro thiazole hydrazone compounds I to IV, combination of the compounds and application thereof to anti-tumor and / or anti-cancer medicine. The invention also relates to a preparation method of the compound. The general chemical formula of the compound is shown as the accompanying drawing, wherein R1, R2 and R3 in the general chemical formula are respectively one kind of materials from H, Br, F and CF3; R1 in the first compound I is Br, and the R2 and the R3 are H; the R1 in the compound II is H, and the R2 and the R3 are F; the R2 in the compound III is CF3; the R1 and the R3 are H; the R2 in the compound IV is H, and the R1 and the R3 are CF3. The invention also relates to a salt containing at least one compound and a physically acceptable inorganic acid or organic acid; if proper, a pharmaceutically acceptable excipient and / or a diluting agent or an excipient can be used. The invention also relates to a formula-shown compound medication preparation containing at least one kind of the compound shown by the structure formula and the salt thereof. The preparation type is tablets, capsules, infusion solutions, suppositories, patches, powder, supensoid agents.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a class of fluorothiazole hydrazone compounds I-IV and their pharmacological activity and pharmaceutical use. The compound and its derivatives can be used to prevent and / or treat diseases such as tumors or cancers caused by various factors. Background technique [0002] Malignant tumors seriously affect people's health and have become the second leading cause of human death, second only to cardiovascular and cerebrovascular diseases. According to the statistics of the World Health Organization, more than 10 million cancer patients are newly diagnosed every year in the world, and the total number of cancer deaths worldwide reaches 7 million people every year. With the aggravation of environmental pollution, the incidence of cancer is increasing year by year, showing a trend of multiple occurrences. The WHO 2014 report predicts that global cancer cases will show a rapid growth t...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/50A61K31/426A61P35/00
CPCC07D277/50
Inventor 史大永王立军郭传龙江波赵越
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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