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

N-substituted benzenesulfonyl-3-propionyl indole derivative, preparation method and application

A kind of technology of propionyl indole and benzenesulfonyl, which is applied in the preparation of N-substituted benzenesulfonyl-3-propionyl indole derivatives, N-substituted benzenesulfonyl-3-propionyl indole derivatives In the field of materials, to achieve the effect of easy operation and simple process

Inactive Publication Date: 2015-11-18
HENAN UNIV OF SCI & TECH
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of N-substituted benzenesulfonyl-3-propionyl indole derivatives and the research on antibacterial activity have not been reported yet.

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
  • N-substituted benzenesulfonyl-3-propionyl indole derivative, preparation method and application
  • N-substituted benzenesulfonyl-3-propionyl indole derivative, preparation method and application
  • N-substituted benzenesulfonyl-3-propionyl indole derivative, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Compound 16:

[0044]

[0045] Its preparation method is:

[0046] Weigh 6-methylindole (1mmol), p-toluenesulfonyl chloride (1.2mmol), sodium hydroxide (1.8mmol) and TEBA (0.1mmol) in a 50mL flask, add dichloromethane (5mL), room temperature React for 1.5h, TLC tracking detection until the reaction is complete, add water (10mL) to stop the reaction, extract with (20mL×3 times) dichloromethane, combine the organic phase, wash the organic phase with saturated sodium chloride solution (10mL), anhydrous sulfuric acid It was dried over sodium and concentrated under reduced pressure to obtain compound 16, which was directly used to prepare compound 1 without isolation.

[0047] The reaction formula for preparing compound 1 from compound 16 is:

[0048]

[0049] Its preparation method is:

[0050] 3mmol of AlCl 3Add to a 50mL flask and add 5mL of dichloromethane, then add 1.5mmol of propionyl chloride at room temperature, after 15 minutes of reaction (that is, after ...

Embodiment 2

[0057] Compound 17:

[0058]

[0059] Its preparation method is:

[0060] Weigh 5-cyanindole (1mmol), p-toluenesulfonyl chloride (1.2mmol), sodium hydroxide (1.8mmol) and TEBA (0.1mmol) in a 50mL flask, add dichloromethane (5mL), room temperature React for 2 hours, TLC tracking detection until the reaction is complete, add water (10mL) to terminate the reaction, extract with (20mL×3 times) dichloromethane, combine the organic phase, wash the organic phase with saturated sodium chloride solution (10mL), anhydrous sodium sulfate Drying and concentration under reduced pressure gave compound 17, which was directly used to prepare compound 2 without isolation.

[0061] The reaction formula for preparing compound 2 from compound 17 is:

[0062]

[0063] Its preparation method is:

[0064] 3mmol of AlCl 3 Add to a 50mL flask and add 5mL of dichloromethane, then add 1.5mmol of propionyl chloride at room temperature, after 15min of reaction (that is, after the reaction soluti...

Embodiment 3

[0075] Compound 18:

[0076]

[0077] Its preparation method is:

[0078] Weigh 6-methylindole (1mmol), p-ethylbenzenesulfonyl chloride (1.2mmol), sodium hydroxide (1.8mmol) and TEBA (0.1mmol) in a 50mL flask, add dichloromethane (5mL), room temperature React for 1.5h, TLC tracking detection until the reaction is complete, add water (10mL) to stop the reaction, extract with (20mL×3 times) dichloromethane, combine the organic phase, wash the organic phase with saturated sodium chloride solution (10mL), anhydrous sulfuric acid It was dried over sodium and concentrated under reduced pressure to obtain compound 18, which was directly used to prepare compound 3 without isolation.

[0079] The reaction formula for preparing compound 3 from compound 18 is:

[0080]

[0081] Its preparation method is:

[0082] 3mmol of AlCl 3 Add it to a 50mL flask and add 5mL of dichloromethane, then add 1.5mmol of propionyl chloride at room temperature, and after 15min of reaction (that is...

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 an N-substituted benzenesulfonyl-3-propionyl indole derivative, a preparation method and application and belongs to the technical field of organic synthesis. The structural formula of the N-substituted benzenesulfonyl-3-propionyl indole derivative is shown in a formula II which is shown in the description. In the formula II, R1 is selected from H, 6-Me or 5-CN; R2 is selected from p-Me, p-Et, m-NO2, p-Cl or p-OMe. The compound is prepared by sulfonylation in nitrogen site and propionylation in C-3 site by taking substituted indole as a raw material. The derivative shows good bacteriostatic activity to 15 plant pathogenic fungi and can be used for preparing a plant pathogenic fungi bacteriostatic agent.

Description

technical field [0001] The invention relates to a kind of N-substituted benzenesulfonyl-3-propionyl indole derivatives, and also relates to the preparation method and application of N-substituted benzenesulfonyl-3-propionyl indole derivatives, belonging to organic synthesis technology field. Background technique [0002] Indole compounds have various biological activities such as anti-inflammation, anti-tumor, anti-bacteria, anti-virus, anti-HIV, etc. In recent years, they have achieved satisfactory clinical effects, and have attracted more and more attention from chemical researchers all over the world. In-depth synthesis of a series of biologically active compounds. For example, Fan et al. reported the research on the anti-HIV-1 activity of N-benzenesulfonyl indole derivatives (Ling-lingFan, Wu-qingLiu, HuiXu, et al. Antihumanimmunodeficiencyvirus-1 (HIV-1) agents 3: Synthesis and invitroanti-HIV -1 activity of some N-arylsulfonylindoles. Chemical & Pharmaceutical Bullet...

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): C07D209/12A01P3/00
CPCA01N43/38C07D209/12
Inventor 陈根强车志平田月娥胡梅王宇
Owner HENAN UNIV OF SCI & TECH
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