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Uvaria macrophylla bisamide derivative and preparation method and application thereof

A Ziyupan, bisamide technology, applied in the separation/purification of carboxylic acid amide, drug combination, pharmaceutical formula, etc., can solve the anti-cancer activity report of the chemical synthesis and preparation method of Ziyupan bisamide derivatives, etc. question

Inactive Publication Date: 2012-01-18
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] But there is no report on the chemical synthesis preparation method and anticancer activity of Ziyupan bisamide derivatives so far

Method used

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  • Uvaria macrophylla bisamide derivative and preparation method and application thereof
  • Uvaria macrophylla bisamide derivative and preparation method and application thereof
  • Uvaria macrophylla bisamide derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1 Preparation of Ziyupan bisamide (1)

[0069] Dissolve benzoic acid (3.7 g, 30 mmol) in 5 mL of thionyl chloride, add 2 drops (0.1 mL) of N,N-dimethylformamide, stir and reflux for about 1 hour, evaporate the solvent to obtain a solid. The solid was dissolved in 50 mL of dichloromethane, and a mixture of 1.32 g (15 mmol) butanediamine and 8 mL of triethylamine was added under cooling, and a solid appeared. After addition, stir at room temperature for 4 h. After the reaction was completed, 50 mL of water was added, filtered, and the filter cake was washed with 5% NaOH and 5% HCl, respectively. The washed solid was suction filtered, and the filter cake was dried to obtain compound (1).

[0070]

[0071] Compound (1) uvariadiamide: n=3, R 1 =R 2 =R 3 =R 4 =H.

[0072] Spectral data of Ziyupan bisamide: ESI-MS m / z 297 [M+H] + , the molecular weight is determined to be 296, and the molecular formula is C 18 h 20 N 2 o 2 . 1 H-NMR (600MHz, DMSO-d...

Embodiment 2

[0073] Example 2 Preparation of Ziyu Panxinsu (2)

[0074] Dissolve p-methoxybenzoic acid (4.5 g, 30 mmol) in 5 mL of thionyl chloride, add 2 drops of N,N-dimethylformamide, stir and reflux for about 1 hour, evaporate the solvent to obtain a solid. The solid was dissolved in 50 mL of dichloromethane, and a mixture of 1.32 g (15 mmol) butanediamine and 8 mL of triethylamine was added under cooling, and a solid appeared. After addition, stir at room temperature for 4 h. After the reaction was completed, 50 mL of water was added, filtered, and the filter cake was washed with 5% NaOH and 5% HCl, respectively. The washed solid was suction filtered, and the filter cake was dried to obtain compound (2).

[0075]

[0076] Compound (2) Violet Pansin (4,4 ′ -di-p-methoxybenzoyl-1,4-butanediamine): n=3, R 2 =R 4 = H, R 1 =R 3 =OCH 3 .

[0077] Ziyu Panxinin is a new natural product, the spectral data of Ziyu Panxinin: ESI-MS m / z 355.6 [M-H] - , with a molecular weight ...

Embodiment 3

[0078] Example 3 4, 4 ′ - Preparation of two p-nitrobenzoyl-1,4-butanediamine (3)

[0079] Dissolve p-nitrobenzoic acid (5 g, 30 mmol) in 5 mL of thionyl chloride, add 2 drops of N,N-dimethylformamide, stir and reflux for about 1 h, evaporate the solvent to obtain a light yellow solid . The yellow solid was dissolved in 50 mL of dichloromethane, and a mixture of 1.32 g (15 mmol) of butanediamine and 8 mL of triethylamine was added under cooling, and a solid appeared. After the addition was complete, stir at room temperature for 4 hours. After the reaction was completed, 50 mL of water was added, filtered, and the filter cake was washed with 5% NaOH and 5% HCl, respectively. The washed solid was suction filtered, and the filter cake was dried to obtain compound (3).

[0080]

[0081] Compound (3) 4,4’-di-p-nitrobenzoyl-1,4-butanediamine: n=3, R 2 =R 4 = H, R 1 =R 3 =NO 2 .

[0082] Its structure confirmed: white powder, ESI-MS: m / z 387.4 [M+H] + , 1 H-NMR (...

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Abstract

The invention relates to an uvaria macrophylla bisamide derivative and a preparation method and application thereof. The invention has the advantages that: the uvaria macrophylla bisamide derivative is subjected to chemical synthesis and research, and a series of novel uvaria macrophylla bisamide derivatives are synthesized; a novel source is provided for the search of anti-cancer medicaments; as proved by a cytotoxin activity experimental result, the varia macrophylla bisamide derivative has a remarkable inhibiting effect on the growth of human lung adenocarcinoma cells and human colon cancer cells; and in particular, uvaria microcarpa neomycin, 4,4'-di-p-dinitrlbinzene formyl-1,4-butanediamine and 4,4'-di-p-methoxy benzoyl-1,6-hexanediamine have remarkable inhibiting effects on the growth of human lung adenocarcinoma cells, so that application to preparation of anti-cancer medicaments is available.

Description

technical field [0001] The present invention relates to a kind of compound and its preparation method and application, in particular, it is a kind of amethyst bisamide derivative, its preparation method and its application in the preparation of anticancer drugs. Background technique [0002] Purple jade plate ( Uvaria microcarpa Champ . ex Benth .), the plant of the genus Ziyupan in the Annonaceae family, is distributed in Guangxi, Guangdong and Taiwan provinces and regions in my country, and its roots are used by folks to treat rheumatism, bruises and low back pain. In recent years, due to the anti-tumor effect of purple jade plate, it has attracted widespread attention from scholars at home and abroad. It is reported in the literature that the plants of the genus Amethyst mainly contain polyoxosubstituted cyclic olefins, annona lactones, flavonoids and alkaloids. In 1982, Jolad et al. first from the genus Amethyst Uvaria accuminata A lactone uvaricin with strong anti...

Claims

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Application Information

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IPC IPC(8): C07C233/78C07C235/50C07C237/34C07C231/24A61K31/166A61P35/00
Inventor 陈海生汤建杨向楠金永生
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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