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Arteannuim derivate substituted by isoxazoline and isoxazolidine and preparation method and application thereof

An unsubstituted and substituent technology, applied in the preparation of anticancer drugs, field of artemisinin derivatives

Inactive Publication Date: 2016-11-23
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, the modified derivatives of artemisinin are still unable to be applied clinically.

Method used

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  • Arteannuim derivate substituted by isoxazoline and isoxazolidine and preparation method and application thereof
  • Arteannuim derivate substituted by isoxazoline and isoxazolidine and preparation method and application thereof
  • Arteannuim derivate substituted by isoxazoline and isoxazolidine and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0157] Embodiment 1, the synthesis of compound S0

[0158]

[0159] The reaction process is shown in scheme1:

[0160]

[0161] Scheme 1

[0162] The preparation of intermediate 1 refers to J.Med.Chem.1997,40,633-638.

[0163] The preparation of intermediate 2 refers to Bioorganic & Medicinal Chemistry Letters.2003,13,1795–1799.

[0164] Intermediate 1 (56mg, 0.2mmol) was dissolved in 2ml of dry CH2Cl2, Intermediate 2 (33mg, 0.21mmol) was added, cooled to 0°C, triethylamine (24mg, 0.22mmol) was slowly added dropwise, and reacted at room temperature for about 12 hours , until the disappearance of intermediate 1 detected by TLC, the reaction was stopped. Add 15 ml of water, extract with CH2Cl2 three times, and the organic layer is washed with water and saturated brine successively, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and separated by column chromatography to obtain 73 mg of the target compound as a white solid. ...

Embodiment 2

[0167] Embodiment 2, the synthesis of compound S1

[0168]

[0169] 1 H NMR (300MHz, Chloroform-d) δ7.58(d, J=8.0Hz, 1H), 6.87(d, J=8.1Hz, 1H), 5.97(s, 1H), 3.91(d, J=17.7Hz ,1H),3.81(s,3H),3.61(d,J=17.7Hz,1H),2.41-2.29(m,2H),2.21-2.15(m,1H),2.10–1.97(m,2H), 1.82-1.77(m,1H),1.54–1.28(m,7H),1.12–0.97(m,4H).

Embodiment 3

[0170] Embodiment 3, the synthesis of compound S2

[0171]

[0172] 1 H NMR (300MHz, Chloroform-d) δ7.70–7.66(m,2H),7.40-7.38(m,3H),6.01(s,1H),3.97(d,J=17.9Hz,1H),3.67( d,J=17.9Hz,1H),2.50–2.32(m,2H),2.26-2.20(dd,J=13.2,4.1Hz,1H),2.14–2.20(m,2H),1.86-1.80(m, 1H),1.56–1.31(m,7H),1.15–1.00(m,4H).

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Abstract

The invention provides an arteannuim derivate containing substitution by isoxazoline and isoxazolidine and a preparation method and application of the arteannuim derivate. Particularly, the invention provides a compound as shown in the following formula I, wherein definitions of all groups are as described in the specification. The compound provided by the invention has the activity of inhibiting a tumor cell from multiplying, and can be used for preparing a medicine for treating a disease relevant to the multiplication of the tumor cell.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to an artemisinin derivative containing isoxazolidine and isoxazolidine, a preparation method thereof, a pharmaceutical composition and its application in the preparation of anticancer drugs. Background technique [0002] Artemisinin is a kind of sesquiterpene lactone extracted from the Compositae plant Artemisia annua, which contains peroxo bridge group sesquiterpene lactone. Artemisinin and its derivatives such as artemether, artesunate, and dihydroartemisinin have been used clinically for many years as highly effective and low-toxic antimalarial drugs. With the in-depth study on the pharmacology of artemisinin, it is found that it also has various biological activities such as anti-schistosomiasis, anti-fungal, and anti-tumor; among them, the role of artemisinin in anti-tumor has attracted more and more attention. [0003] In 1991, Chinese scholar Deng Anding report...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/22C07D519/00A61K31/424A61K31/439A61K31/5386A61K31/5377A61K31/4748A61K31/437A61K31/496A61P35/00A61P35/02
CPCC07D498/22C07D519/00
Inventor 张翱缪泽鸿刘刚宋姗姗丁春勇
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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