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5-bromo oxoisoaporphine, and synthesis method and application thereof

A technique for synthesizing 5-bromooxyisoaporphine, which is applied in the field of medicine, can solve problems such as the synthesis method and application of 5-bromooxyisoaporphine, and achieve significant in vitro antitumor activity and good medicinal value.

Inactive Publication Date: 2013-04-17
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no related report about 5-bromooxyisoaporphine and its synthetic method and application in the prior art

Method used

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  • 5-bromo oxoisoaporphine, and synthesis method and application thereof
  • 5-bromo oxoisoaporphine, and synthesis method and application thereof
  • 5-bromo oxoisoaporphine, and synthesis method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035] 1) Synthesis of intermediate 1 (4-bromophenethylamine):

[0036] Dissolve 0.2mol of lithium aluminum hydride in 200mL of anhydrous ether, and dissolve 0.2mol of 4-bromophenylacetonitrile in 50mL of anhydrous ether. Slowly add the anhydrous ether solution of 4-bromophenylacetonitrile dropwise. After the addition is complete, stir and react at room temperature for 6 hours, neutralize with saturated sodium sulfate solution until no bubbles are generated, filter the reaction solution with suction, wash the filter residue with chloroform, and depressurize The solvent was distilled off to obtain intermediate 1 (colorless and slightly viscous 4-bromophenethylamine liquid), with a yield of 40%;

[0037] 2) Synthesis of Intermediate 2:

[0038] Mix and dissolve 0.1 mol of phthalic anhydride and 0.1 mol of intermediate 1 in 200 mL of ethanol, reflux at 90°C for 8 hours, cool the reaction solution to room temperature, and precipitate colorless crystals, filter them with suction, ...

Embodiment 2

[0050] 1) Synthesis of intermediate 1 (4-bromophenethylamine):

[0051] Dissolve 0.1 mol of lithium aluminum hydride in 100 mL of anhydrous ether, and dissolve 0.2 mol of 4-bromophenylacetonitrile in 50 mL of anhydrous ether. Slowly add the anhydrous ether solution of 4-bromophenylacetonitrile dropwise. After the addition is complete, stir and react at room temperature for 8 hours, neutralize with saturated sodium sulfate solution until no bubbles are generated, filter the reaction solution with suction, wash the filtrate with chloroform, and depressurize The solvent was distilled off to obtain intermediate 1 (colorless and slightly viscous 4-bromophenethylamine liquid), with a yield of 20%;

[0052] 2) Synthesis of Intermediate 2:

[0053] Take 0.1mol of phthalic anhydride and 0.1mol of intermediate 1, mix and dissolve in 50mL of ethanol, reflux at 95°C for 2 hours, suction filter while it is hot, cool the filtrate to room temperature, and precipitate colorless crystals, suc...

Embodiment 3

[0059] 1) Synthesis of intermediate 1 (4-bromophenethylamine):

[0060] Dissolve 0.4mol of lithium aluminum hydride in 300mL of anhydrous ether, and dissolve 0.2mol of 4-bromophenylacetonitrile in 50mL of anhydrous ether. Slowly add the anhydrous ether solution of 4-bromophenylacetonitrile dropwise. After the addition is complete, stir the reaction at room temperature for 2 hours, neutralize with saturated sodium sulfate solution until no bubbles are generated, filter the reaction solution with suction, wash the filtrate with chloroform, and depressurize The solvent was distilled off to obtain intermediate 1 (colorless and slightly viscous 4-bromophenethylamine liquid), with a yield of 30%;

[0061] 2) Synthesis of Intermediate 2:

[0062] Take 0.12mol of phthalic anhydride and 0.1mol of intermediate 1, mix and dissolve in 50mL of ethanol, reflux at 100°C for 12 hours, suction filter while it is hot, cool the filtrate to room temperature, and precipitate colorless crystals, s...

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Abstract

The invention discloses a 5-bromo oxoisoaporphine, and a synthesis method and application thereof. The synthesis route of the 5-bromo oxoisoaporphine comprises the following steps: reducing 4-bromobenzylcyanide used as an initial raw material to obtain 4-bromobenzylethylamine, reacting the 4-bromobenzylethylamine with phthalic anhydride, and performing Friedel-Crafts acylation cyclization reaction twice, thus obtaining the 5-bromo oxoisoaporphine through synthesis. The applicant surveys the proliferation inhibition activity of the 5-bromo oxoisoaporphine on multiple human tumor cell strains, and results show that the 5-bromo oxoisoaporphine has remarkable in-vitro antitumor activity, has good potential pharmaceutical values and is hopefully used for the preparation of various antitumor medicaments. The chemical structural formula of the 5-bromo oxoisoaporphine is shown as below in the specification.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to 5-bromooxyisoaporphine and its synthesis method and application. Background technique [0002] In 1982, Kunitomo et al. isolated and identified the first oxidized isoaporphine alkaloid, menisporphine, from the plant Pueraria chinensis in the family Pueraria chinensis. Later, researchers isolated four alkaloids of the same type from this plant. So far, more than a dozen oxidized isoapomorphine-type alkaloids have been isolated, mainly including: gyrothine, gyroline, gyrophenamine, gyrophenorine, etc. [0003] In terms of organic synthesis, as early as 1953, King synthesized the mother nucleus of the oxidized isoaporphine alkaloid, that is, 1-azabenzanthrone; but at that time it was only used as a dye, and its pharmacological activity was not investigated. Research. In 1984, Iwashima et al. carried out organic total synthesis of 1-azabenzanthrone through a simpler and faster syn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18A61K31/473A61P35/00
Inventor 陈振锋梁宏刘延成唐煌张传辉覃其品
Owner GUANGXI NORMAL UNIV
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