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Synthetic method of oxidized nantenine and application of oxidized nantenine

A technology of nandinaphylline and its synthesis method, which is applied in the field of medicine and can solve problems such as the organic synthesis method of oxidized nandinaphylline that has not yet been seen

Inactive Publication Date: 2015-03-04
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Oxidized nantianaine can be obtained by separation and extraction from plants such as Lauraceae, Fangjiaceae, and Annonaceae (Si Duanyun, Hopphenidoid alkaloid components in the aerial parts of Fangji, Journal of Jining Medical College, Vol. 14, No. 2, June 1991), but up to now there is no relevant report on the organic synthesis method and application of oxidized nandinaphylline

Method used

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  • Synthetic method of oxidized nantenine and application of oxidized nantenine
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  • Synthetic method of oxidized nantenine and application of oxidized nantenine

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Embodiment 1

[0049] Embodiment 1: Preparation of oxidized nandinaphylline

[0050] 1) Synthesis of intermediate 1:

[0051] Weigh 0.2 mol of pepper acetic acid, dissolve it in 200 mL of glacial acetic acid with stirring, and slowly add 0.2 mol of bromine water dropwise. After the dropwise addition, react at 10° C. for 1 h, then pour the reaction solution into ice water, let stand, and filter with suction to obtain a white powder of Intermediate 1 with a yield of 60%.

[0052] 2) Synthesis of Intermediate 2:

[0053] Weigh 0.2 mol of intermediate 1, dissolve it in 200 mL of chloroform, slowly add 0.3 mol of thionyl chloride, and react under reflux at 60° C. for 4 h. After cooling, the solvent was evaporated to dryness to obtain a brown oil, which was dissolved in 400 mL of chloroform to obtain solution A. Dissolve 0.2 mol of 3,4-dimethoxyphenethylamine in 400 mL of chloroform, then add 400 mL of ammonia solution, and stir to obtain solution B (at this time, the pH of solution B=8.5). Un...

Embodiment 2

[0073] 1) Synthesis of intermediate 1:

[0074] Weigh 0.2 mol of pepper acetic acid, dissolve it in 500 mL of glacial acetic acid with stirring, and slowly add 0.6 mol of bromine water dropwise. After the dropwise addition, the reaction was continued at 35° C. for 6 h, and then the reaction solution was poured into ice water, left to stand, and suction filtered to obtain a white powder of Intermediate 1 with a yield of 90%.

[0075] 2) Synthesis of Intermediate 2:

[0076] Weigh 0.2 mol of intermediate 1, dissolve it in a total of 600 mL of a solvent obtained by mixing dichloromethane and ethyl acetate at a ratio of 3:1, slowly add 0.8 mol of thionyl chloride, and react under reflux at 120°C for 12 hours. After cooling, the solvent was evaporated to dryness to obtain a brown oil, which was dissolved in 600 mL of dichloromethane to obtain solution A. Dissolve 0.2mol of 3,4-dimethoxyphenethylamine in 600mL of dichloromethane, then add 600mL of saturated aqueous sodium bicarbon...

Embodiment 3

[0088] 1) Synthesis of Intermediate 1:

[0089] Weigh 0.2 mol of pepper acetic acid, dissolve it in 300 mL of glacial acetic acid with stirring, and slowly add 0.4 mol of bromine water dropwise. After the dropwise addition, the reaction was continued at 25° C. for 4 h, and then the reaction solution was poured into ice water, left to stand, and suction filtered to obtain a white powder of Intermediate 1 with a yield of 85%.

[0090] 2) Synthesis of Intermediate 2:

[0091] Weigh 0.2 mol of intermediate 1, dissolve it in 400 mL of ethyl acetate, slowly add 0.3-0.8 mol of thionyl chloride, and react under reflux at 100°C for 8 hours. After cooling, the solvent was evaporated to dryness to obtain a brown oil, which was dissolved in 500 mL of ethyl acetate to obtain solution A. Dissolve 0.2 mol of 3,4-dimethoxyphenethylamine in 500 mL of ethyl acetate, then add 500 mL of aqueous sodium hydroxide solution, and stir evenly to obtain solution B (at this time, the pH of solution B=1...

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Abstract

The invention discloses a synthetic method of oxidized nantenine and application of the oxidized nantenine. The synthetic method of the oxidized nantenine comprises the following steps: taking 2-(benzo[d][1,3]dioxol-5-yl)acetic acid and 3,4-dimethoxy phenethylamine as starting materials, and conducting seven-step reaction to synthesize the oxidized nantenine. Compared with the prior art, the organic complete synthetic method of the oxidized nantenine is provided by the invention; experiments indicate that the oxidized nantenine has a proliferation inhibitory activity against a plurality of human tumor cell strains, shows up a good antitumor activity in vitro, is excellent in potential medicinal value, and can be applied to preparation of various anti-tumor drugs.

Description

technical field [0001] The invention relates to a synthesis method and application of oxidized nandinaphylline, belonging to the technical field of medicine. Background technique [0002] Oxidized aporphina alkaloids belong to natural isoquinoline alkaloids, which are widely found in plants such as Magnoliaceae, Lianthaceae, Rutaceae, Anemoneaceae, and Fangheceae. At present, there are more than 30 kinds of oxidized aporphilkaloids that have been extracted and isolated from natural products, most of which have significant pharmacological activity. For example, the half maximal inhibitory concentration (IC 50 values) were less than 8 μM; the oxidized aporphiline derivatives extracted from Yushan Tangsongcao had good proliferation inhibitory effect on malignant tumor cell lines such as KB, A549, HCT-8, P-388 and L-1210, and its IC 50 The values ​​are all less than 10 μM. Two oxidized aporphyllines, oxidized anurine and oxidized sea papaverine, were isolated from the ethano...

Claims

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Application Information

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IPC IPC(8): C07D491/06A61K31/4741A61P35/00
CPCC07D491/06
Inventor 陈振锋梁宏刘延成曹东张业黄克斌
Owner GUANGXI NORMAL UNIV
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