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Preparation method and use of 3,3'-methylenebis(1H-Indole)

A technology based on bisindole and indole, which is applied in the directions of medical preparations containing active ingredients, pharmaceutical formulations, organic active ingredients, etc. The effect of cheap and simplified operation steps

Active Publication Date: 2014-09-03
SOURCING BIZ GUILIN INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the catalyst production process is cumbersome and relatively expensive

Method used

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  • Preparation method and use of 3,3'-methylenebis(1H-Indole)
  • Preparation method and use of 3,3'-methylenebis(1H-Indole)
  • Preparation method and use of 3,3'-methylenebis(1H-Indole)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] The room temperature synthesis of the methylenyl bisindole that embodiment 1 p-toluenesulfonic acid and a certain proportion of water and technical ethanol participate in

[0101] The synthetic reaction equation is as follows:

[0102]

[0103] The synthesis process is as follows:

[0104] After adding 29.5 grams of indole and 0.45 grams of p-toluenesulfonic acid into the four-necked flask, add 150 mL of industrial alcohol with a mass fraction of 95% and 100 mL of water to completely dissolve the reaction substrate indole, and drop it under nitrogen protection and mechanical stirring. Add 10 mL of 40% formaldehyde aqueous solution, and react at room temperature (25-30° C.) for 24 hours after the dropwise addition, and a solid product will be precipitated during the reaction.

[0105] Identification of the product:

[0106] The remaining reaction solution and sampled raw material solution in the above reaction process were taken for thin-layer chromatography (TLC) m...

Embodiment 2

[0108] The purification of embodiment 2 methylene bisindole

[0109] The reaction system carried out in Example 1 was filtered to separate the solid product, which was the crude product; the separated reaction liquid was distilled under reduced pressure to recover the ethanol therein.

[0110] Experiments have found that the solid product is directly recrystallized, and the water in it will greatly affect the yield and purity of recrystallization purification, so rinsing is required. Take 31.7 g of the wet solid product isolated in Example 1 (that is, it does not need to be dried and does not affect the crystallization efficiency), and the crude product is rinsed with 120 mL of methanol under vacuum filtration.

[0111] The washed solid product was mixed with 60 mL of ethyl acetate, heated to 70-78°C with stirring to dissolve, then naturally cooled to room temperature, and the solid was precipitated by filtration. Then, add 50 mL of ethyl acetate to the solid, heat to 70-78 °...

Embodiment 3

[0112] The drug application test of embodiment 3 methylenyl bisindole

[0113] All cell lines used in this assay can be purchased from the American Type Culture Collection (ATCC).

[0114] 1. In vitro killing experiment of Colon38 cells

[0115] Source: Colon38 cells are mouse colon cancer cells, which are adherent cells.

[0116] Medium: 164090% (culture solution) + NCS (newborn calf serum) 10% + 1ml penicillin streptomycin mixed solution

[0117] Culture conditions: in 5% CO 2 cultured in a 37°C incubator. Subculture once every 3 days, and start the experiment when the cells enter the logarithmic growth phase after 2-3 passages.

[0118] Experimental steps: (1) Take the cultured cells in the logarithmic growth phase, blow them out evenly, and prepare a single cell suspension;

[0119] (2) Adjust the cell concentration to 2×10 with RPMI1640 culture medium containing 10% FBS 5 / mL, seeded in 96-well cell culture plate, 100 μL per well, placed at 37°C, 5% CO 2 Cultivate ...

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Abstract

The invention provides a preparation method of 3,3'-methylenebis(1H-Indole). The preparation method comprises the following steps that 1, indole and p-toluenesulfonic acid are dissolved in a solvent comprising water and 95wt% of ethanol and a formaldehyde aqueous solution is added into the mixed solution in a nitrogen protective atmosphere; 2, the mixture obtained by the step 1 undergoes a reaction at a room temperature in dark for 20 to 30 hours, preferably, for 24 hours; 3, reaction products are filtered so that solids precipitated by the step 2 are obtained; and 4, the solids obtained by the step 3 are subjected to recrystallization purification. In addition, the invention also provides a use of the prepared 3,3'-methylenebis(1H-Indole) which is a high purity compound in preparation of drugs.

Description

field of invention [0001] The invention belongs to the field of medicine, in particular, the invention relates to a production method and drug application of 3,3'-methenyl bisindole. Background technique [0002] 3,3'-Methylene bis indole (3,3'-methylenebis (1H-Indole)) (CAS registration number: 1968-05-4) structure is shown below, in nature for terrestrial or marine organisms Metabolites with certain medicinal value: [0003] [0004] Several methods have been developed to synthesize 3,3'-methenylbisindole and its analogues. For example, B.P.Bandgar et al. (Bandgar, B.P.; Shaikh, K.A.Tetrahedron Lett.2003,44,1959-1961.) have reported a method (reaction formula is as follows ). But the fly in the ointment is that a large amount of Na must be used for post-reaction treatment 2 S 2 o 3 , has certain pollution to the environment, and poisonous acetonitrile is used as a solvent in the reaction and does not conform to the concept of green environmental protection. [00...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08A61K31/404A61P35/00
Inventor 詹姆斯·周陈东刘尚钟
Owner SOURCING BIZ GUILIN INC
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