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Diindolylmethane compound as well as synthesis method and application thereof

A bis-indolylmethane compound technology, applied in the field of organic compound synthesis, can solve the problems of low yield, long reaction time, strong corrosion, etc., and achieve the effect of reasonable and easy synthesis method, rapid reaction and good selectivity

Inactive Publication Date: 2016-06-01
NANJING POLYTECHNIC INSITUTE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] According to published literature (see Chem.Eur.J., 2005,11,3077; CN201280025088.1; CN201310278480.3), the synthesis of this type of compound basically adopts the conventional heating and reflux method of substituted benzaldehyde and indole esters , the catalyst used is concentrated sulfuric acid or concentrated hydrochloric acid, which has the disadvantages of long reaction time, low yield and strong corrosion

Method used

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  • Diindolylmethane compound as well as synthesis method and application thereof
  • Diindolylmethane compound as well as synthesis method and application thereof
  • Diindolylmethane compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of Methyl 3,3'-Benzylidene Bisindole-2-carboxylate

[0034] Dissolve 0.35g of methyl indole-2-carboxylate in 15mL of anhydrous acetonitrile in a 50mL one-necked flask, then add 0.11g of benzaldehyde and 0.06g of bismuth trifluoromethanesulfonate, and place the three-necked flask in a microwave reactor , reacted under 400W power for 10min, and TLC (20% ethyl acetate-petroleum ether) detected that the reaction was complete. After cooling and standing still, crystals were precipitated, filtered, washed, and recrystallized with absolute ethanol to obtain 0.40 g of a white solid, with a yield of 91.3%. m.p.239.3~240.2℃; 1 HNMR(300MHz,DMSO)δ11.79(s,2H),7.58–7.35(m,3H),7.26(d,J=6.4Hz,3H),7.14(t,J=6.9Hz,4H),6.75– 6.56(m,4H),3.78(s,6H); MSm / z:438.16,461.2(M+Na) + .

Embodiment 2

[0036] Synthesis of Methyl 3,3'-(3-Nitrobenzylidene)bisindole-2-carboxylate

[0037] Dissolve 0.35g of methyl indole-2-carboxylate in 15mL of anhydrous acetonitrile in a 50mL one-necked flask, then add 0.15g m-nitrobenzaldehyde and 0.06g bismuth trifluoromethanesulfonate, and place the three-necked flask in a microwave In the reactor, react under 300W power for 10min, and TLC (20% ethyl acetate-petroleum ether) detects that the reaction is complete. After cooling and standing still, crystals were precipitated, filtered, washed, and recrystallized from absolute ethanol to obtain 0.45 g of a yellow solid, with a yield of 93.1%. m.p.249.5~250.6℃; 1 HNMR (300MHz, DMSO) δ11.93(s, 2H), 8.14(td, J=4.7, 2.6Hz, 2H), 7.86(s, 2H), 7.58(d, J=6.0Hz, 2H), 7.48( d, J=8.3Hz, 2H), 7.16(t, J=7.6Hz, 2H), 6.72(t, J=7.6Hz, 2H), 6.60(d, J=8.3Hz, 2H), 3.78(s, 6H); MSm / z: 483.14, 506.1 (M+Na) + .

Embodiment 3

[0039] Synthesis of Methyl 3,3'-(4-Methylbenzylidene)bisindole-2-carboxylate

[0040] Dissolve 0.35g of methyl indole-2-carboxylate in 15mL of anhydrous acetonitrile in a 50mL one-necked flask, then add 0.12g of p-tolualdehyde and 0.06g of bismuth trifluoromethanesulfonate, and place the three-necked flask in a microwave In the reactor, the reaction was carried out under 500W power for 12 minutes, and TLC (20% ethyl acetate-petroleum ether) detected that the reaction was complete. After cooling and standing still, crystals were precipitated, filtered, washed, and recrystallized from anhydrous acetonitrile to obtain 0.41 g of a white solid, with a yield of 91.1%. m.p.239.6~241.3℃; 1 HNMR(300MHz,DMSO)δ11.74(s,2H),7.52–7.34(m,3H),7.20–7.09(m,2H),7.03(dd,J=23.8,7.9Hz,4H),6.76–6.59 (m,4H),3.76(s,6H),2.29(s,3H); MSm / z:452.17,475.2(M+Na) + .

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Abstract

The invention discloses a diindolylmethane compound as well as a synthesis method and application thereof, and belongs to the technical field of organic compound synthesis. The diindolylmethane compound has the structure as shown in the description. The synthesis method of the diindolylmethane compound comprises the following steps: dissolving indole-2-methyl formate and substituted benzaldehyde in a round-bottom flask by using a solvent, adding a catalyst, putting into a microwave reactor for reflux reaction, after the reaction is completed, leaving to stand to separate solid, filtering, and recrystalizing the solid, thereby obtaining a product. The diindolylmethane compound can be used as a precursor compound for synthesizing a novel magnetic resonance targeted contrast agent, is also a potential anti-tumor medicine, and has relatively high market application values.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, and specifically belongs to a class of bis-indolylmethane compounds and a synthesis method and application thereof. Background technique [0002] In nature, especially in organisms, alkaloids containing indole rings account for about 1 / 5 of the total alkaloids. These compounds have good pharmacological and biological activities, and their antibacterial and antioxidant activities are used in in antibiotic drugs. As metabolites of many terrestrial and marine organisms, bis-indolylmethane derivatives have more abundant physiological activities, and are mainly used for antibacterial, treatment of fibromyalgia, long-term fatigue, acute enteritis, promotion of estrogen metabolism in the human body, energy Effectively inhibit the growth of cancer cells, especially have good inhibitory activity on the growth of breast cells. Peng Shiqi and others announced a class of aryl-substituted...

Claims

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Application Information

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IPC IPC(8): C07D209/42A61K49/06A61P35/00
CPCC07D209/42A61K49/06
Inventor 孙宏顺李玉龙胡瑾蒋蕻潘勇许宁徐媛媛周进
Owner NANJING POLYTECHNIC INSITUTE