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Lactone compound of sweetsop connected through amido bond, synthetic method and application

A technology of anemone lactone and compound, which is applied in the field of synthesis of chiral anemone lactone analogues, and can solve problems such as low synthesis efficiency, poor water solubility, and limited research progress of finished medicines

Inactive Publication Date: 2007-12-26
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

In this series of compounds, the carbon skeleton of the molecule is constructed through the connection of ether bonds, which makes its synthesis efficiency not high; and the water solubility of this series of compounds is poor, which will limit the progress of its later drug research

Method used

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  • Lactone compound of sweetsop connected through amido bond, synthetic method and application
  • Lactone compound of sweetsop connected through amido bond, synthetic method and application
  • Lactone compound of sweetsop connected through amido bond, synthetic method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056]

[0057] Under cooling in an ice-water bath, 4.14 g of Dess-Martin oxidant was added to a solution of 2.00 g of compound 18 in 50 mL of dichloromethane. The reaction system was stirred at room temperature for 2 hours, quenched with saturated sodium sulfite solution, extracted with ethyl acetate, and the combined organic phase was washed with saturated sodium bicarbonate and saturated sodium chloride in sequence, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The above crude product and 9.6 mL of 2-methyl-2-butene were dissolved in 40 mL of tert-butanol, cooled to 0°C, and a 10 mL aqueous solution of 2.22 g of sodium chlorite and 3.35 g of potassium dihydrogen phosphate was slowly added dropwise. The reaction mixture was stirred overnight at room temperature, the solvent was spinned out under reduced pressure, extracted with ethyl acetate, the organic phases were combined and washed with saturated brine, dried over anhydrous ...

Embodiment 2

[0064]

[0065] Under cooling in an ice bath, a solution of 102 mg TBDPSCl in 5 mL of dichloromethane was slowly added dropwise to 100 mg of diol 20 and 50 mg of imidazole in 5 mL of dichloromethane. After the reaction mixture was stirred at room temperature for 2 hours, 0.58 mL of Li-Pr 2 After NEt was cooled to 0°C, 0.12 MLMOMCl was slowly injected. The reaction system was stirred overnight at room temperature, quenched with saturated ammonium chloride, and extracted with ethyl acetate. The combined organic phases were washed with 1N hydrochloric acid saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and column chromatography gave a colorless Liquid 175mg, yield 90%.

[0066] [α] D 25 =-15.30 (c1.70, CHCl 3 );

[0067] 1 H NMR (400MHz, CDCl 3 ): 1.05(9H, s), 1.29(20H, m), 1.62(4H, m), 2.30(2H, t, J=7.5Hz), 3.34(3H, s), 3.64(6H, m), 4.64 (1H, d, J=6.7 Hz), 4.77 (1H, d, J=6.8 Hz), 7.39 (6H, m), 7.68 (4H, m) ppm;

[0068] MS (ESI, m / z): 6...

Embodiment 3

[0071]

[0072] At -78°C, slowly add 0.34 mL (1.6 Minhexane) n-butyl lithium dropwise to 0.12 mL of diisopropylamine in 3 mL of THF, and after stirring for 30 minutes, slowly add 0.16 g of compound 21 in 5 mL of anhydrous THF dropwise to the reaction system solution, and after continuing to stir for 30 min, a freshly prepared solution of 0.087 g of aldehyde 23 in 3 mL of anhydrous THF was slowly added dropwise. After the reaction system was stirred for 2 hours, it was quenched with saturated ammonium chloride, and the system was extracted with ethyl acetate. The combined organic phases were washed with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product that was dissolved in 10 mL of THF and added with 1 mL of 10 %H 2 SO 4 , stirred at room temperature for 24 hours, quenched with saturated sodium bicarbonate and extracted with ethyl acetate, the combined organic phases were washed with saturated sodium chlori...

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Abstract

This invention relates to an acetogenin compound linked by amide bonds, its synthesis method and its application. The acetogenin compound is an optically active or racemized compound, whose structural formula is shown in this invention, wherein, Y is C6-20 alkyl; n is 0-3; m is 7-19; R1, R2, R3 and R4 are the same or not, and are H or C1-10 alkyl; when n is 0-2, R3 and R4 are H, Cl, C1-10 alkyl or combined to form fiver-, six- or seven-membered ring shape; when n is 0, R1 and R2 are C1-10 alkyl or combined to form fiver-, six- or seven-membered ring shape. The acetogenin compound has high anticancer activity, and IC50 (mu.M) is lower than 0.04 to breast cancer (MDA-MB-435S). The can be manufactured into anticancer drugs. The synthesis method is simple, and suitable for industrial production.

Description

technical field [0001] The invention relates to a lactone compound, in particular to a synthesis method and application of a chiral anemone lactone analog connected by an amide bond. 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. Lo...

Claims

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Application Information

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IPC IPC(8): C07D307/58A61K31/365A61K31/496A61P35/00
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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