Hydroxy substituted tetrahydro-beta-carboline small-molecular organic compounds, as well as derivatives and medical application thereof

A technology of organic compounds and small molecules, applied in the field of medicine, can solve the problems of poor physical and chemical properties, not being widely used, and low bioavailability

Inactive Publication Date: 2018-11-02
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to their cytotoxicity, low bioavailability and poor physical and chemical properties, this type of structure has not been widely used.

Method used

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  • Hydroxy substituted tetrahydro-beta-carboline small-molecular organic compounds, as well as derivatives and medical application thereof
  • Hydroxy substituted tetrahydro-beta-carboline small-molecular organic compounds, as well as derivatives and medical application thereof
  • Hydroxy substituted tetrahydro-beta-carboline small-molecular organic compounds, as well as derivatives and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Embodiment one: the preparation of each compound

Embodiment 1-1

[0097] Example 1-1, Synthesis of 6-(2-hydroxyethylamine) carbonyl-N-phenylacetyl-1,3,4,9-tetrahydro-9H-β-carboline (IM001)

[0098]

[0099] Take 4-hydrazinobenzoic acid methyl ester hydrochloride (405mg, 2mmol) and 4-chlorobutyraldehyde dimethyl acetal (367mg, 2.4mmol) and dissolve in 18mL ethanol-water mixed solvent (V / V, 5 / 1) After about 18 hours of reaction, the solution turned reddish brown, and the solvent was distilled off under reduced pressure. After evaporating to dryness, dissolve it with methanol (25mL), heat and stir, and when the temperature is 80°C, add SOCl dropwise 2 , then continued to heat and reflux at 80° C. for 1-2 hours, evaporated to dryness, and purified by column chromatography to obtain 6-methoxycarbonyltryptamine (205 mg, yield: 47%);

[0100] Dissolve 6-methoxycarbonyltryptamine (205 mg, 0.94 mmol) in glacial acetic acid (5 mL), add formaldehyde solution (71 μL, 0.94 mmol) dropwise under nitrogen protection, react at room temperature overnight,...

Embodiment 1-1 to 1-35

[0104] The preparation method of table 1. embodiment 1-1 to 1-35 compound IM-001 to IM-035

[0105]

[0106]

[0107]

[0108]

[0109]

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PUM

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Abstract

The invention discloses hydroxy substituted tetrahydro-beta-carboline small-molecular organic compounds and derivatives, hydrates or pharmaceutically acceptable salts of the compounds, pharmaceuticalcomposition containing the compounds, an application of the compounds to preparation of drugs for preventing and / or treating various USP (ubiquitin-specific protease)15-mediated malignant tumors and tumor metastasis related diseases.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a hydroxyl-substituted tetrahydro-β-carboline small molecule organic compound and its derivatives and their medical application. Background technique [0002] With the development of the global economy, the acceleration of globalization, the deterioration of the ecological environment and the change of lifestyle, the frequency of risk factors for malignant tumors is increasing, and the incidence and mortality of malignant tumors are on the rise all over the world. It has become a serious threat to human beings. Major public health issues of life and social development. According to the World Health Organization, the number of cancer patients worldwide is increasing at an alarming rate. According to the latest statistics from CA in the United States, in 2017, there will be 1.68 million new cases of cancer in the United States, and compared with 2000, the proportion of new patients...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61K31/4545A61P35/04A61P35/00A61P35/02
CPCA61P35/00A61P35/02A61P35/04C07D471/04
Inventor 陈益华王平裴海翔陈云飞高丹刘明耀罗剑
Owner EAST CHINA NORMAL UNIV
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