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

Synthesis method and anti-tumor application of bisindole-pyridine derivatives

A technology of indolopyridines and derivatives is applied in the directions of antitumor drugs, drug combinations, organic chemistry, etc., and achieves the effects of simple operation process, low cost and strong inhibitory effect.

Active Publication Date: 2019-01-08
CHONGQING UNIV OF ARTS & SCI
View PDF3 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are not many reports on multi-component reactions of similar structural compounds, and more attention and research are urgently needed

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
  • Synthesis method and anti-tumor application of bisindole-pyridine derivatives
  • Synthesis method and anti-tumor application of bisindole-pyridine derivatives
  • Synthesis method and anti-tumor application of bisindole-pyridine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] where R 1 is phenyl, R 2 is a hydrogen atom, R3 is a hydrogen atom, that is, the synthesis of 6-phenyl-7,12-dihydropyrido[3,2-b:5,4-b']diindole, the specific steps are as follows:

[0052] In a 5 mL microwave reaction tube, dissolve 0.5 mmol of benzaldehyde and 0.5 mmol of Boc-protected indoleamine in 2 mL of methanol, stir at room temperature for 5 minutes, then add 0.05 mmol of perchloric acid and 0.5 mmol of benzyl isocyanide, respectively . and placed in a microwave reactor for 100 o C for 10 minutes. After the completion of the reaction, cool to room temperature, pour the reaction solution into 15 mL ethyl acetate, wash with saturated sodium bicarbonate and brine, dry the organic phase with anhydrous sodium sulfate, concentrate, and use ethyl acetate / n-hexane (20-80%) gradient The target compound 6-phenyl-7,12-dihydropyrido[3,2-b:5,4-b']diindole was obtained by elution and separation with a yield of 76%.

[0053] 1 H NMR (400 MHz, DMSO- d 6 ) δ 12.95 (s, 1H...

Embodiment 2

[0055] where R 1 is an alkyl group, R 2 is a hydrogen atom, R 3 is a hydrogen atom, that is, the synthesis of 6-cyclohexyl-7,12-dihydropyrido[3,2-b:5,4-b']diindole, the specific steps are as follows:

[0056] In a 5 mL microwave reaction tube, dissolve 0.5 mmol of cyclohexylaldehyde and 0.5 mmol of Boc-protected indoleamine in 2 mL of methanol, stir at room temperature for 5 minutes, and then add 0.05 mmol of perchloric acid and 0.5 mmol of benzyl isonitrile . and placed in a microwave reactor for 100 o C for 10 minutes. After the completion of the reaction, cool to room temperature, pour the reaction solution into 15 mL ethyl acetate, wash with saturated sodium bicarbonate and brine, dry the organic phase with anhydrous sodium sulfate, concentrate, and use ethyl acetate / n-hexane (20-80%) gradient The target compound 6-cyclohexyl-7,12-dihydropyrido[3,2-b:5,4-b']diindole was obtained by elution and separation with a yield of 72%.

[0057] 1 H NMR (400 MHz, CDCl 3 ) δ 8....

Embodiment 3

[0059] where R 1 is aryl, R 2 is a hydrogen atom, R 3 is a hydrogen atom, that is, the synthesis of 6-(4-bromophenyl)-7,12-dihydropyrido[3,2-b:5,4-b']diindole, the specific steps are as follows:

[0060] In a 5 mL microwave reaction tube, dissolve 0.5 mmol of 4-bromophenylaldehyde and 0.5 mmol of Boc-protected indoleamine in 2 mL of methanol, stir at room temperature for 5 minutes, and then add 0.05 mmol of perchloric acid and 0.5 mmol of benzyl isonitrile. and placed in a microwave reactor for 100 o C for 10 minutes. After the completion of the reaction, cool to room temperature, pour the reaction solution into 15 mL ethyl acetate, wash with saturated sodium bicarbonate and brine, dry the organic phase with anhydrous sodium sulfate, concentrate, and use ethyl acetate / n-hexane (20-80%) gradient The target compound 6-(4-bromophenyl)-7,12-dihydropyrido[3,2-b:5,4-b']diindole was obtained by elution and separation with a yield of 83%.

[0061] 1 H NMR (400 MHz, DMSO- d 6 ...

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 simple preparation method and application of bisindole-pyridine derivatives. The simple preparation method and application of the bisindole-pyridine derivatives provided bythe invention has the advantages that on the basis of three-component reaction, methanol is used as a solvent under acid conditions for synthesis of the bisindole-pyridine derivatives through microwave-assisted reaction ring closing; and the bisindole-pyridine derivatives are antitumor-active, and particularly achieve strong inhabiting effects on HCT116 colon cancer cells.

Description

technical field [0001] The application relates to the field of drug synthesis, especially a rapid preparation method of bisindolopyridine derivatives and its application in antitumor drugs. Background technique [0002] Indolopyridine derivatives are a class of very broad biological and pharmaceutical activities, good therapeutic properties, and can be used to prepare new compounds that inhibit protein kinase activity; treat diabetes, hypertension, hyperlipidemia, hypercholesterolemia and cardiovascular disease Drugs for complications; compounds that can also be used as kinase inhibitors; drugs that improve cellular immunity, antiviral, antibacterial, antimicrobial activity, and treat tumors or psychosis. [0003] Common pyridine compounds include imidazopyridine, benzopyridine, pyridopyridine, thienopyridine, pyrazolopyridine, furopyridine and indolopyridine, especially indolopyridine compounds, which can be used directly It is used in the preparation of angiotensin-inhibi...

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): C07D401/14A61P35/00
CPCA61P35/00C07D401/14
Inventor 徐志刚陈中祝张亚军
Owner CHONGQING UNIV OF ARTS & 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