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

1,3,4 - Trisubstituted pyrrole compound and preparation method and application thereof

A compound, three-substituted technology, applied in the field of medicine, can solve problems such as unreported

Inactive Publication Date: 2014-08-20
SHANGHAI JIAO TONG UNIV
View PDF8 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the literature has never reported the application of 1, 3, 4-substituted pyrrole compounds in antitumor

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
  • 1,3,4 - Trisubstituted pyrrole compound and preparation method and application thereof
  • 1,3,4 - Trisubstituted pyrrole compound and preparation method and application thereof
  • 1,3,4 - Trisubstituted pyrrole compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0050] Implementation case 1, 3-(4-methoxyphenyl)-4 nitropyrrole

[0051] Under the protection of nitrogen, add 4-methoxyphenylnitroethylene (0.18g, 1mmol) and p-toluenesulfonate methyl isocyanide (0.23g, 1.2mmol) to 10mLDMSO, slowly add tert-butanol Potassium (0.15g, 1.3mmol), stirred at room temperature for 3 hours, quenched the reaction by adding saturated aqueous ammonium chloride solution, extracted three times with dichloromethane, dried over anhydrous sodium sulfate, distilled off the solvent, silica gel column chromatography (petroleum Ether: ethyl acetate=3:1), a solid (0.17g) was obtained, and the reaction yield was 79%. 1 HNMR (300MHz, CDCl 3 )δ(ppm):8.551(1H,s),7.741(1H,m),7.381(2H,d,J=4.8Hz),6.935(2H,d,J=4.2Hz),6.706(1H,m) ,3.845(3H,s).

Embodiment example 2

[0052] Implementation case 2, N-bromoethyl-3-(4-fluorophenyl)-4 cyanopyrrole

[0053] Under nitrogen protection, 3-(4-fluorophenyl)-4-cyanopyrrole (0.19g, 1mmol), 1,2-dibromoethane (0.56g, 3mmol) and potassium carbonate (1.38g , 10mmol), heated at 80°C for 8 hours, after the reaction, add 20mL of water, extract three times with dichloromethane, dry over anhydrous sodium sulfate, evaporate the solvent, silica gel column chromatography (petroleum ether: ethyl acetate = 6:1 ), a solid (67 mg) was obtained, and the reaction yield was 23%. 1 HNMR (300MHz, CDCl 3 )δ(ppm):7.933(2H,d,J=8.1Hz),7.367(2H,d,J=8.1Hz),7.249(1H,s),6.896(1H,s),4.320(2H,t, d=6.3Hz),3.622(2H,t,d=6.3Hz).

Embodiment example 3

[0054] Implementation case 3, N-methyl-3-4-methoxy-4-nitropyrrole

[0055] Under the protection of nitrogen, add 3-(4-methoxy)-4-nitropyrrole (0.218g, 1mmol), iodomethane (0.42g, 3mmol) and potassium carbonate (1.38g, 10mmol) in 15mL DMF, room temperature Stir for 5 hours. After the reaction is over, add 20 mL of water, extract three times with dichloromethane, dry over anhydrous sodium sulfate, evaporate the solvent, perform silica gel column chromatography (petroleum ether: ethyl acetate = 6:1), and obtain the product, pale Yellow solid, the reaction yield is 88%. 1 HNMR (300MHz, CDCl 3 )δ(ppm):7.555(1H,s),7.342(2H,d,J=9Hz),6.903(2H,d,J=9Hz),6.496(1H,s),3.833(3H,s),3.715 (3H).

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 a 1,3,4-trisubstituted pyrrole compound and a preparation method and application thereof, The 1,3,4-trisubstituted pyrrole compound is characterized in that the compound has a structure in the following formula, and can be used as an anticancer drug. Compared with the prior art, a series of 1,3,4-trisubstituted pyrrole compound provided by the invention has stronger antitumor activity in vitro, and so can be used as a new class of anticancer drug.

Description

technical field [0001] The invention relates to the pharmaceutical industry, in particular to the antitumor application of a class of 1,3,4-trisubstituted pyrrole compounds. Background technique [0002] Pyrrole is a nitrogen-containing five-membered heterocyclic ring with weak aromaticity, which exists in a large number of natural compounds and plays an important role as the core structure. Pyrrole compounds are widely used in the field of medicine. International Patent Document No. WO8706266 (A1) discloses an excellent anti-inflammatory drug and analgesic drug Ketorolac (ketorolac), which works by inhibiting the production of prostaglandins. International Patent Document No. WO9961476 (A1) discloses a pyrrole ring-containing compound SU-5416, which is an ATP competitive inhibitor of tyrosine kinase of Flk-1 / KDR receptor, and can be used to treat malignant tumors such as melanoma and colon cancer. U.S. Patent Document No. US4089951 discloses the non-steroidal anti-inflamma...

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 Patents(China)
IPC IPC(8): C07D207/42C07D207/34C07D207/333C07D405/04A61P35/00
Inventor 毛振民兰天詹晓平
Owner SHANGHAI JIAO TONG 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