Hepta(6-(isoquinoline-3-amido)-6-deoxy)-β-cyclodextrin and its preparation method and application

A kind of technology of cyclodextrin and isoquinoline, which is applied in the field of biomedicine and can solve the problems such as antitumor activity of uninstructed compounds

Inactive Publication Date: 2018-07-27
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the prior art does not teach that this compound has antitumor activity

Method used

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  • Hepta(6-(isoquinoline-3-amido)-6-deoxy)-β-cyclodextrin and its preparation method and application
  • Hepta(6-(isoquinoline-3-amido)-6-deoxy)-β-cyclodextrin and its preparation method and application
  • Hepta(6-(isoquinoline-3-amido)-6-deoxy)-β-cyclodextrin and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Preparation of (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (1)

[0018] Put HCl (320ml) and HCHO (160ml) in a 500ml eggplant bottle, add L-Phe (30.10g, 182.45mmol) after mixing, react in an oil bath at 95°C for 24h, stop the reaction, and cool to room temperature. The pH was adjusted to 6-7 with saturated NaOH in an ice bath, and a large amount of white solids precipitated out. Filtration gave a white solid (21.80 g, 67.54%). ESI-MS(m / z): 178.1[M+H] + .

Embodiment 2

[0019] Example 2 Preparation of (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester (2)

[0020] Add methanol (100ml) to a 250ml eggplant bottle, add thionyl chloride (15ml) drop by drop in an ice-salt bath, stir for 30min, then slowly add (3S)-1,2,3,4-tetrahydroisoquinoline -3-Carboxylic acid (1) (10.00g, 56.50mmol), reacted for 9-10h, and the reaction solution was drained to obtain a white solid (8.46g, 78.40%). ESI-MS(m / z): 192.0[M+H] + .

Embodiment 3

[0021] Example 3 Preparation of methyl isoquinoline-3-carboxylate (3)

[0022] Add (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester (2) (4.23g, 22.15mmol) in a 250ml eggplant bottle, add N,N- Dissolve it in dimethylformamide (50ml), add 2.97g (18.79mmol) of potassium permanganate, react for 6h, add ethanol (50ml) and stir for 30min, remove the solvent, add methanol (30ml) to redissolve. Separation and purification by column chromatography gave a colorless solid (858mg, 24.56%). ESI-MS(m / z): 188.0[M+H] + .

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Abstract

The present invention relates to a compound seven (6-(isoquinoline-3-amido)-6-deoxy)-β-cyclodextrin with anti-tumor activity and a preparation method thereof. Application in tumor medicine. The compound of the present invention has cytotoxicity in vitro and anti-tumor activity in vivo, and relates to the inhibitory effect on the cytotoxic activity of five tumor cell proliferations of A549, HCT-8, HeLa, SW480, and S180. The compound of the present invention has good anti-tumor activity and can It is used in the preparation of antitumor drugs, and the invention belongs to the field of biomedicine.

Description

technical field [0001] The invention belongs to the field of biomedicine. Specifically, the present invention relates to a seven (6-(isoquinoline-3-amido)-6-deoxy)-β-cyclodextrin and its preparation method, and further relates to the use of the compound in the preparation of antitumor drugs application. Background technique [0002] Malignant tumor is a multiple disease, which has caused serious harm to human health. The development of clinical chemotherapy drugs for malignant tumors has always been one of the hot spots in tumor research. As we all know, the research on isoquinoline alkaloids has become one of the hot spots in the research and development of anticancer drugs, especially in the discovery of new drugs and their lead compounds. Among them, isoquinoline-3-carboxylic acid exhibits certain antitumor activity, but due to poor solubility and low bioavailability, it cannot exert antitumor function well. The existing technology, such as the Chinese patent applicat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16A61K31/724A61P35/00
Inventor 李莉赵明彭师奇马秋冉
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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