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Annonaceous acetogenin compound and synthesis method and application thereof

A technology of annua lactone and a compound, which is applied in the simplified field of annua lactone compound and its synthesis, can solve the problems of not obtaining a compound, restricting research on finished drugs, etc., and achieves high anticancer activity and selectivity, and low-cost and easy-to-use raw materials. The effect of obtaining and preparation method is simple

Inactive Publication Date: 2013-08-28
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in these compounds, the left side chains are all flexible alkyl chains, and no rigid structural left side chain modifiers and compounds with symmetrical dilactone five-membered ring structures have been obtained, which will limit the development of later stages. drug research

Method used

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  • Annonaceous acetogenin compound and synthesis method and application thereof
  • Annonaceous acetogenin compound and synthesis method and application thereof
  • Annonaceous acetogenin compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]

[0045] Take 0.07moL of compound 20 in a single-necked bottle, add 1.6g of benzyltriethylammonium chloride, 0.084moL of compound 21, stir at room temperature for 3min, slowly add 55mL of 50% sodium hydroxide solution, and stir vigorously at room temperature for 3.5h , add 40mL water to quench the reaction, the reaction solution is extracted with 40mL×3 ether, the organic phases are combined and washed with saturated ammonium chloride and sodium chloride solution successively, dried over anhydrous sodium sulfate, concentrated and column chromatography to obtain a colorless liquid 22 (11.7 g, 80%).

[0046] [α] 25 D : 6.1 (c 2.6, CHCl 3 ).

[0047] 1 H NMR (400MHz, CDCl 3 ): δ7.35-7.27(m, 5H), 4.58(s, 2H), 3.80(dd, J=11.6, 3.0Hz, 1H), 3.75-3.63(m, 4H), 3.45(dd, J=11.6 , 5.8Hz, 1H), 3.18-3.16(m, 1H), 2.80-2.78(m, 1H), 2.62(dd, J=5.0, 2.7Hz, 1H) ppm; HRMS (ESI): C 12 h 16 o 3 calculated[M+H] + 209.1172, found 209.1175, [M+Na] + 231.0992, found 231.0988.

Embodiment 2

[0049]

[0050] At -78°C under the protection of argon, slowly add 13 mmol of n-BuLi (2.5M in hexane) dropwise to 13 mmol of compound 23 in 20 mL of anhydrous tetrahydrofuran, react for 45 minutes, and slowly add 13 mmol of BF 3 ·Et 2 O, after reacting for 30 minutes, slowly add 6.5 mmol of compound 22 in 5 mL of anhydrous tetrahydrofuran solution, continue to stir for 3 h, quench the reaction with 5 mL of saturated ammonium chloride solution, spin off tetrahydrofuran under reduced pressure, and extract with 15 mL×3 diethyl ether, The organic phases were combined and washed successively with saturated sodium bicarbonate and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and the intermediate obtained by concentration was dissolved in 20 mL of anhydrous dichloromethane, and 52 mmol of diisopropyl Ethylamine, after cooling to 0°C, slowly add 32.5mmol of MOMCl, stir the reaction at room temperature for 20h, quench the reaction with 5mL of saturated amm...

Embodiment 3

[0055]

[0056] Dissolve 4.26mmol of intermediate 24 in 20ml of absolute ethanol, add 0.302g (20%m) of 10% Pd / C, 2.0mL of glacial acetic acid, react for 16h under the action of hydrogen balloon, and filter with diatomaceous earth , washed with ethanol, concentrated to obtain the intermediate, added 5.11mmol of 21 at room temperature, 0.18g of benzyltriethylammonium chloride, slowly added 3.5mL of 50% NaOH aqueous solution, stirred at room temperature for 22h, diluted with 3mL of water, 15 mL×3 of diethyl ether was extracted, the organic phases were combined and washed successively with saturated ammonium chloride and sodium chloride, dried over anhydrous sodium sulfate, concentrated and column chromatographed to obtain light yellow liquid compound 25 (0.99 g, 72%).

[0057] [α] 25 D =-1.8 (C=1.11, CHCl 3 );

[0058] 1 H NMR (400MHz, CDCl 3 ): δ7.28-7.15(m, 5H), 4.76(d, J=6.8Hz, 1H), 4.64(d, J=6.8Hz, 1H), 3.77(dd, J=11.7, 2.8Hz, 1H) , 3.74-3.38(m, 8H), 3.36(s, 3H), 3.1...

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Abstract

The invention discloses an R or S-shaped or racemic annonaceous acetogenin compound with a structure of a formula 1. In the formula, R1 is alkane of C2 to C10, five to seven-element naphthenic hydrocarbon or five-element alpha or beta unsaturated lactonic ring, or substituted benzene ring or naphthalene ring compound; R2 is H or OH; x is 0 to 5, y is 1 to 6, n is 3 to 5, and m is 7 to 19; and when x is 0, y is 1 and n is 3, R1 is alkane of C2 to C10, five to seven-element naphthenic hydrocarbon or substituted benzene ring or naphthalene ring, and R2 is H or OH; or when x is 1 to 5 and y is 6,the R1 is five-element alpha or beta unsaturated lactonic ring, and R2 is hydroxy. The preparation raw materials for the compound are cheap and easily obtained; the preparation method is simple and suitable for industrialized production; and the compound has high anti-tumor activity, and can be used for preparing anti-tumor medicaments. Formula 1.

Description

technical field [0001] The present invention relates to a lactone compound, in particular to a simplified anemone lactone compound and its synthesis method and application. Background technique [0002] Currently, cancer has become one of the greatest threats to human health. According to the statistics of the World Health Organization (WHO), in recent years, the number of patients who die of cancer in the world is as high as 7 million every year, which is very close to the number of people who die of acute cardiovascular and cerebrovascular diseases. Cancer is about to replace cardiovascular and cerebrovascular diseases as the number one killer of human health. The current methods for treating cancer, such as surgical resection, radiotherapy, chemotherapy and gene therapy, all have certain defects, such as large toxic and side effects or incomplete treatment. With the development of modern organic separation and identification and chemical synthesis technology, many scien...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/58A61K31/365A61P35/00
CPCY02P20/55
Inventor 蒋晟姚祝军周光飚肖奇才刘永强
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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