Method for preparing unsymmetrical bis(indolyl)methane compound

A technology for diindolylmethane and compounds is applied in the field of preparing asymmetric diindolylmethane compounds, and achieves the effects of simple reaction system, high atom economy, and good anti-senile dementia effect.

Inactive Publication Date: 2009-11-25
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
View PDF0 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the reported methods for the synthesis of bis-indolylmethane derivatives, most of them focus on symmetrical bis-indolylmethane compounds, while there are fewer synthetic methods for asymmetric bis-indol

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
  • Method for preparing unsymmetrical bis(indolyl)methane compound
  • Method for preparing unsymmetrical bis(indolyl)methane compound

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0016] Example 1

[0017] Synthesis of 3a

[0018] Add 0.5 to 500 mL of water to a dry 1 to 1000 milliliter (ml) reaction flask, and add 0.01 to 10 mmol of InX 3 , 0.2-200mmol substrate 1a and 0.3-300mmol substrate 2a, stir and react at a certain temperature for 5 hours, extract the aqueous phase with ethyl acetate, dry the organic phase with anhydrous sodium sulfate, concentrate, and purify by fast silica gel column chromatography to obtain product 3a .

[0019] White solid 1 H NMR (400MHz, Acetone-d 6 ): δ9.90(s, 1H), 9.79(s, 1H), 7.91(d, J=8.4Hz, 1H), 7.32-7.40(m, 4H), 7.22-7.28(m, 2H), 7.19( s, 1H), 7.16 (s, 1H), 7.05 (t, J=7.2Hz, 7.2Hz, 1H), 6.89 (t, J=7.2Hz, 7.2Hz, 2H), 6.67 (s, 1H), 6.62 (s, 1H), 2.25 (s, 3H); 13 C NMR(125MHz, Acetone-d 6 ): δ169.8, 146.7, 140.0, 136.5, 136.3, 131.9, 131.6, 131.0, 130.9, 128.5, 128.2, 128.0, 126.6, 125.0, 124.8, 124.7, 123.8, 122.1, 120.4, 120.0, 119.4, 112.1, 111.8, 35.9, 21.7; EI-HRMS m / z calculated value C 25 H 20 N 2 O 2 : 380.1525[M]...

Example Embodiment

[0020] Example 2

[0021] Synthesis of 3b

[0022] The operation is the same as in Example 1.

[0023] White solid 1 H NMR (400MHz, Acetone-d 6 ): δ 11.23 (s, 1H), 9.93 (s, 1H), 9.79 (s, 1H), 7.87-7.91 (m, 1H), 7.42-7.53 (m, 1H), 7.35-7.38 (m, 2H) ), 7.19-7.29 (m, 3H), 7.11 (s, 1H), 7.06 (t, J=8.4 Hz, 7.2 Hz, 1H), 6.85-6.91 (m, 2H), 6.69-6.74 (m, 3H) , 3.60(s, 3H); 13 C NMR(100MHz, Acetone-d 6 ): δ169.2, 153.6, 145.8, 137.3, 132.4, 131.1, 130.8, 130.1, 129.9, 127.8, 127.4, 125.8, 124.7, 124.0, 121.3, 119.7, 118.9, 118.8, 118.7, 118.5, 111.9, 111.3, 101.6, 54.3, 35.1

Example Embodiment

[0024] Example 3

[0025] Synthesis of 3c

[0026] The operation is the same as in Example 1.

[0027] White solid 1 H NMR (400MHz, Acetone-d 6 ): δ11.22(s, 1H), 9.93(s, 1H), 9.81(s, 1H), 7.90(d, J=7.2Hz, 1H), 7.36-7.43(m, 6H), 7.24-7.31( m, 6H), 7.11 (s, 1H), 7.01-7.05 (m, 2H), 6.89 (t, J = 8.0 Hz, 7.2 Hz, 1H), 6.80 (d, J = 8.8 Hz, 1H), 6.72 ( s, 1H), 4.91 (s, 2H); 13 C NMR(100MHz, Acetone-d 6 ): δ169.5, 152.7, 145.8, 138.2, 137.3, 132.5, 131.1, 130.7, 130.1, 128.3, 127.7, 127.5, 127.4, 127.3, 125.8, 124.7, 124.0, 121.3, 119.6, 119.5, 118.9, 118.8, 118.5, 112.0, 111.9, 111.3, 103.2, 70.2, 35.2

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 method for preparing unsymmetrical bis-indolyl substituted methane compound. The method is realized by using Friedel-Crafts reaction catalyzed by InX. The method has the advantages of moderate reaction condition, easy and simple operation, good substrate adaptability with water as dissolvant, friendly environment, convenient separation and purification, application prospect for synthesizing unsymmetrical bis(indolyl)methane compound in a large scale.

Description

Technical field [0001] The invention relates to a method for preparing asymmetric bisindole methane compounds. Background technique [0002] Indole compounds are widespread in nature, and many indole derivatives have certain physiological and pharmacological activities. Among them, diindolylmethane and its derivatives, as metabolites of terrestrial and marine organisms, have a wide range of important physiological activities such as anti-tumor, anti-viral, anti-bacterial, and anti-inflammatory, and have always been organic chemists and pharmaceutical research hotspots. [0003] Bisindole methane compounds are usually synthesized from aldehydes or ketones and indole in the presence of catalysts. The currently reported catalysts include montmorillonite K-10 and LiClO 4 , In(OTf) 3 , I 2 And Michler’s acid, etc. The use of these catalysts can synthesize bis-indole methane derivatives with better yields. However, most of the methods for synthesizing bis-indole methane derivatives tha...

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): C07D209/18C07D405/14A61K31/405A61P25/28
Inventor 林国强孙兴文林华沈少春臧杨
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap