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Derivate of sweetsop lactone as well as preparation method and usage

A technology of anemone lactone and derivatives, which is applied in the field of new anemone lactone derivatives, and can solve problems such as difficult chemical synthesis, many chiral centers, and complex structures

Inactive Publication Date: 2005-07-06
SOUTH CHINA PLANT INST CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the structural patterns of these patented compounds, there are tetrahydrofuran rings, many chiral centers, and complex structures, which are difficult to chemically synthesize. Therefore, people have carried out a lot of researches based on the structure-activity relationship of the annona lactone compound. Simplify Synthetic Research
In China, Wu Yulin and others removed the carbon bridge of the tetrahydrofuran ring and retained the ether oxygen group, and successively synthesized two kinds of non-THF annulus lactone derivatives with anticancer activity, but the structure is relatively complicated (CN 97106368.0; CN 99125750.2)

Method used

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  • Derivate of sweetsop lactone as well as preparation method and usage
  • Derivate of sweetsop lactone as well as preparation method and usage
  • Derivate of sweetsop lactone as well as preparation method and usage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment one: the extraction and the separation of anemone diesterin

[0025] The dry powder of custard apple seeds (1 kg) is soaked in 95% ethanol three times, each time for 2 days, and the ethanol extract is concentrated to dryness under reduced pressure to obtain a syrupy ethanol extract. Dissolve the ethanol extract in 300mL 80% dilute ethanol, extract three times with petroleum ether, 100mL each time, wash the petroleum ether extract three times with 80% ethanol, 100mL each time, and merge the washing liquid into the dilute ethanol solution after petroleum ether extraction middle. After the dilute ethanol solution was evaporated to remove ethanol under reduced pressure, water was added to 200 mL to form an aqueous suspension. The aqueous suspension was extracted three times with 100 mL of chloroform. The chloroform extract was dried over anhydrous sodium sulfate and then concentrated to dryness to obtain a brown oil (brown solid at room temperature), which was ...

Embodiment 2

[0027] Embodiment two: structural identification

[0028] Annona diacetin: white needle-like crystals, melting point: 94-96°C; [α] D 24 -3.3° (c0.122, acetone). EI-MSm / z(%): 381[M+H] + (9), 362 [M-H 2 O] + (70), 344(13), 334(8), 295(98), 277(12), 251(18), 112(65), 111(51), 95(78), 85(100), major The interpretation of the fragment ion peaks is given in Formula III. 1 H NMR (CDCl 3 , 400Mz): See Table 1. 13 C NMR (CDCl 3 , 100Mz): See Table 1.

[0029]

[0030] No. δ H (J in Hz) δ C

Embodiment 3

[0031] Example Three: Cytotoxicity to Human Cancer Cells

[0032] Human cancer cell lines: human liver cancer cell line (Bel-7402) and human nasopharyngeal carcinoma cell line (CNE2).

[0033] Main reagents and instruments: RPMI~1640 culture medium, thiazole blue powder (MTT), cisplatin (DDP), enzyme-linked detector

[0034] Test method: use thiazolium blue reduction method (MTT method). The specific method is: under sterile conditions, take the above-mentioned human cancer cells, and adjust them into 1 ≅ 105 / ml The cell suspension was distributed in 96-well cell culture plate, 0.2ml per hole, no drug control group, DMSO solvent control group, known anticancer drug DDP group and 5~6 test substance groups with different concentrations were set up. Set up 4 parallel wells in each group, add drugs to act for 48 hours, measure the OD value of each well on the enzyme-linked analyzer, and calculate according to the fo...

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Abstract

The present invention provides a novel annonaceous acetogenin derivative, whose structural formula (II) is: ∴ It is extracted and separated from the Annonaceae plant. Its use is as a drug to treat cancer.

Description

technical field [0001] The present invention relates to a novel annona lactone derivative, further relates to its preparation method, and further relates to its use in preparing anticancer drugs. Background technique [0002] Annonaceous acetogenins are a kind of long-chain fatty acid γ-lactone derivatives unique to some plants of Annonaceae. The structural characteristics of this kind of substance are: there is a methyl-substituted α, β-unsaturated γ-lactone ring at one end of a long fatty chain, 1-3 tetrahydrofuran rings and other oxygen-containing substituents on the fatty chain , such as hydroxyl, acetoxy, ketone, epoxy, etc., and carbon-carbon double bonds. In recent years, some tetrahydropyran ring and tetrahydrofuran ring-free annona lactone derivatives have also been discovered. Annonaceolide compounds have been paid attention to because of their strong biological activity. In 1988 and 1989, Mikolajczak et al. obtained two invention patents for pest control (US Pa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N43/08A61K31/34A61K47/22A61P35/00C07D307/58
Inventor 魏孝义谢海辉徐志防杨仁洲
Owner SOUTH CHINA PLANT INST CHINESE ACAD OF SCI
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