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Simple method for preparing ellipticine or substituted ellipticine

A technology for ellipticine and a preparation process, which is applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of low total yield, harsh reaction conditions, and difficulty in obtaining raw materials, and achieves simple and convenient process operation and high total yield. Effect

Active Publication Date: 2020-05-05
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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Problems solved by technology

[0008] Literature (Backvall JE, Plobeck NA. New synthesis of the 6H-pyrido[4,3-b]carbazoles ellipticine and olivacine via cycloloaddition of 2-phenylsulfonyl 1,3-dienes to indoles[J]. J Org Chem, 1990,55 : 4528-4531) reported a new synthesis process of ellipticine, the process reaction conditions are harsh, raw materials are difficult to obtain, and the total yield is low

Method used

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  • Simple method for preparing ellipticine or substituted ellipticine
  • Simple method for preparing ellipticine or substituted ellipticine
  • Simple method for preparing ellipticine or substituted ellipticine

Examples

Experimental program
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Embodiment 1

[0039] The preparation of embodiment 1 ellipticine

[0040] Preparation of Intermediate 2

[0041] Add 11.7g (0.1mol) indole and 11.4g (0.1mol) 2,5-hexanedione in a round-bottomed flask, mix and stir until dissolved, add 0.03 equivalents of montmorillonite powder loaded with p-toluenesulfonic acid in advance, in React in a microwave reactor for 10 min. The reaction solution was cooled to room temperature, diluted with ethyl acetate, and the montmorillonite catalyst was filtered off. The solid was washed with ethyl acetate, and the organic phase was washed with saturated sodium carbonate solution, purified water, and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. overnight. Concentrate to obtain 17.5 g of white solid, yield 90.0%. m.p.92-93℃. 1 H NMR (500MHz, CDCl 3 )δ8.16(d, J=7.8Hz, 1H), 7.45-7.36(m, 2H), 7.23(s, 1H), 7.11(d, J=7.2Hz, 1H), 6.92(d, J=7.2 Hz,1H),2.83(s,3H),2.48(s,3H)( figure 1 ).

[0042] Preparation of Intermediate 3

[0...

Embodiment 2

[0050] The preparation of embodiment 2 9-methoxy ellipticine

[0051]

[0052] Preparation of Intermediate 8

[0053] Add 14.7g (0.1mol) of 5-methoxyindole and 13.5g (0.1mol) of 2,5-hexanedione into a round-bottomed flask, mix and stir until dissolved, add 0.03 equivalents of Mongolian pre-loaded with p-toluenesulfonic acid Destoned powder, react in microwave reactor for 10min. The reaction solution was cooled to room temperature, diluted with ethyl acetate, and the montmorillonite catalyst was filtered off. The solid was washed with ethyl acetate, and the organic phase was washed with saturated sodium carbonate solution, purified water, and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. overnight. Concentration gave 8 as a white solid (19.7 g, 87.6% yield, melting point 135-137°C).

[0054] Preparation of Intermediate 9

[0055] Add 3.85g (28.5mmol) of N-methyl-N-phenylformamide into the three-necked flask, slowly add 4.62g (29.5mmol) of p...

Embodiment 3

[0061] Embodiment 3 ellipticine chromatographic analysis method

[0062] Ellipticine purity adopts HPLC method to measure, with ODS-3C18 chromatographic column, packing particle size 5μm, size 250×4.6mm, gradient elution with water (0.01% TFA)-methanol (0.01% TFA) as mobile phase (5%-95% methanol), flow rate 1.8ml / min, the column temperature is 45°C, the detection wavelength is 299nm, the elution time is 60min, and the purity of ellipticine calculated by area normalization is 95.75% ( Figure 7 and table below).

[0063] peak# keep time area high peak start peak end area% 1 27.52 7985137 545938 27.147 30.453 95.74627 2 43.187 126005 9103 42.901 43.616 1.456051 3 44.152 54325 2600 43.616 44.587 0.627764 4 45.241 173047 12995 45.003 48.32 1.999545 5 46.283 14746 1184 46.059 46.581 0.170368

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Abstract

The invention relates to a synthesis process for preparing ellipticine. Ellipticine is obtained through six steps of reaction and three steps of crystallization separation, the target product total yield is high, column chromatography separation is not needed for an intermediate product and the target product, and the method is particularly suitable for large-scale preparation.

Description

technical field [0001] The invention relates to a preparation process of ellipticine. The biggest feature of the process is that the products in each step do not need to be separated by column chromatography, the total yield is high and the process is simplified, and it is especially suitable for large-scale preparation. Background technique [0002] Ellipticine (also known as elliptic ellipticine) naturally exists in the leaves of Ochrosia elliptica Labill., the bark and leaves of O. balansae, Mohs rose tree ( O.moorei) and other plants, can be obtained by chemical synthesis. It belongs to cytotoxic alkaloids, has anti-tumor effect, and can inhibit the activity of topoisomerase IIα (Topo IIα). French scientists have shown that ellipticine derivatives can effectively inhibit the spread of tumors, and at the same time, they have strong anti-metastasis activity and produce relatively small side effects. This research result will open up a new way for cancer treatment. [000...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04Y02P20/55
Inventor 潘显道林菁菁沈珑瑛杜国华
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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