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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
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  • Summary
  • Abstract
  • Description
  • Claims
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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-indolylmethane compounds, based on bis-indolylmethane The important use of indole methane compounds, the development and synthesis of asymmetric indole-substituted bis-indole methane compounds has important significance

Method used

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  • Method for preparing unsymmetrical bis(indolyl)methane compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 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] + ; Measured value...

Embodiment 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

Embodiment 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

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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

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Application Information

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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
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