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Chirality anona squamosa L. lactone compound with conformation limitation structure and synthesizing method and use thereof

A kind of annua lactone, a technology of limiting structure, applied in the field of chiral annua lactone analogs and their synthesis, and can solve the problems such as not obtaining chiral products and the like

Inactive Publication Date: 2008-01-23
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of compound is synthesized from a chiral hydroxy acid raw material to an epoxy intermediate containing substituted or rearranged γ-butyrolactone, and the polyethylene glycol compound and the epoxy intermediate are coupled, catalytically hydrogenated, and eliminated. The product anemone lactone analog was obtained but the chiral product was not obtained by this method

Method used

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  • Chirality anona squamosa L. lactone compound with conformation limitation structure and synthesizing method and use thereof
  • Chirality anona squamosa L. lactone compound with conformation limitation structure and synthesizing method and use thereof
  • Chirality anona squamosa L. lactone compound with conformation limitation structure and synthesizing method and use thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056]

[0057] Dissolve 4.76mmol of 60% sodium hydride in 10mL of DMF, cool to 0°C and slowly drop into 15mL of the raw material 4.76mmol of diol in DMF, stir at this temperature for 30 minutes, then slowly drop into 15mL of the raw material 2.38mmol of 14 DMF solution, the temperature of the reaction solution was slowly raised to 80° C. after dropping, and reacted for 15 hours. Cool to room temperature, quench with saturated ammonium chloride, dilute the system with 150mL ethyl acetate, separate the organic phase, wash with water, saturated ammonium chloride and saturated sodium chloride successively, dry over anhydrous sodium sulfate, filter, concentrate, and obtain by column chromatography Pale yellow liquid 16 (0.53 g, 82%).

[0058] [α] D 25 =+3.6(c 3.1, CHCl 3 );

[0059] 1 H NMR (400MHz, CDCl 3 )δ: 0.88 (3H, t, J=7.0Hz), 1.23 (16H, m), 1.52 (2H, m), 3.37 (3H, s), 3.38 (3H, s), 3.39 (3H, s), 3.53-3.78 (8H, m), 3.87 (1H, dd, J = 5.5, 10.0Hz), 4.64 (5H, m), 4.75...

Embodiment 2

[0063]

[0064] Add 0.21 g of tetrabutylammonium bisulfate as a phase transfer catalyst to the 40 mL cyclohexane solution of raw materials 4.8 mmol 16 and 9.6 mmol epichlorohydrin, stir evenly and cool to 0 ° C, slowly add 10 mL of 50% NaOH aqueous solution dropwise, at room temperature After stirring at low temperature for 10 hours, the system was diluted with 100 mL ether, the organic phase was separated, washed with water and saturated sodium chloride successively, dried over anhydrous sodium sulfate, concentrated, and column chromatography gave colorless liquid 17 (1.42 g, 60%).

[0065] [α] D 25 =-15.5(c 2.1, CHCl 3 );

[0066] 1 H NMR (500MHz, CDCl 3 )δ: 0.88 (3H, t, J = 7.0Hz), 1.26 (16H, m), 1.55 (2H, m), 2.60 (1H, m), 2.77 (1H, dd, J = 4.2, 5.0Hz), 3.15(1H,m), 3.36(6H,m), 3.37(3H,s), 3.54-3.76(10H,m), 3.84(1H,m), 4.63(5H,m), 4.77(1H,d, J = 6.7Hz) ppm;

[0067] 13 C NMR (100MHz, CDCl 3 )δ: 96.7, 96.6, 95.9, 79.38, 79.32, 76.4, 73.8, 72.2, 72.0, 67.1, 66.8, ...

Embodiment 3

[0071]

[0072] -78°C and under the protection of nitrogen, slowly drop 4.38mmol n-BuLi (1.6M in hexane) into 4.38mmol trimethylsilylacetylene in 5mL anhydrous tetrahydrofuran, stir for 30 minutes, then add 4.38mmol BF 3 ·Et 2 O, after continuing to stir for 30 minutes, slowly drop into 15mL of anhydrous tetrahydrofuran solution of compound 1.46mmol 17, after 2 hours of reaction, quench with saturated ammonium chloride, dilute the system with 50mL of ether, separate the organic phase with saturated sodium bicarbonate and Wash with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate to obtain the intermediate, dissolve in 10 mL of anhydrous dichloromethane, add 21.9 mmol of diisopropylethylamine at room temperature, cool to 0 ° C, slowly inject 14.6 mmol of MOMCl, React at room temperature for 5 hours, quenched with saturated sodium bicarbonate, dilute the system with 50 mL of dichloromethane, separate the organic phase, wash with 1N HCI, saturated sodi...

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Abstract

The invention relates to the chemical compound of the chiral annonaceous acetogenins of the comformational restriction structure, the synthetic method and the purpose. The compound has the optical activity compound as the above formula: (R or S configuration) (R or S configuration). The compound of the invention has high anti-cancer activity and selectivity and has the IC50 (MuM) of the human breast duct cancer reaching less than 0.04, and the suppressive activity on the cancer cell is about 100 times that of the normal cell and has better selectivity. The compound of the invention can also be used as the anti-cancer drug and has simple preparation method, which is a method suitable for the industrial production.

Description

technical field [0001] The present invention relates to a lactone compound, in particular to a chiral anemone lactone analogue and its synthesis method and application. Background technique [0002] Currently, cancer has become the greatest threat to human health, and its incidence is increasing year by year. Cancer is responsible for more than 20% of all deaths each year, a figure that exceeds the combined number of deaths from AIDS, tuberculosis and malaria. Traditional cancer treatment methods, such as surgical resection, radiotherapy and chemotherapy, have certain defects, either incomplete treatment or severe side effects. With the development of modern organic separation identification and synthesis technology, many chemists are committed to the separation and identification of natural compounds with high anti-tumor activity and selectivity from natural products, and obtain this natural compound with relatively high content through organic synthesis. Low compounds, a...

Claims

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Application Information

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IPC IPC(8): C07D307/58C07D307/60C07D409/12A61K31/365A61K31/381A61P35/00
CPCY02P20/55
Inventor 姚祝军刘海侠张焕明
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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