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Artemisinin derivatives containing isothiocyanate group and application thereof

A technology of artemisinin derivatives and isothiocyanic acid, which is applied in the field of medicine, can solve problems such as difficult radical cures, and achieve high cytotoxicity and good curative effect

Active Publication Date: 2018-09-28
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although surgical treatment has significantly improved the survival period of patients with glioma, drug therapy is still one of the important means of treating glioma due to the difficulty of radical cure. Research and development of new chemotherapeutic drugs is an important way to control the progression of the disease

Method used

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  • Artemisinin derivatives containing isothiocyanate group and application thereof
  • Artemisinin derivatives containing isothiocyanate group and application thereof
  • Artemisinin derivatives containing isothiocyanate group and application thereof

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preparation example Construction

[0031] The present invention also provides a preparation method of the above-mentioned compound of formula I.

[0032] The embodiments of the present invention specifically describe three embodiments of the compound of formula I above: X is methylene, and n=0, n=1 or n=4.

[0033] Please see the following synthetic routes:

[0034]

Embodiment 1

[0036] Example 1 provides the preparation method of 5a in the above synthetic route, where X in formula I is methylene, and n=0.

[0037] details as follows:

[0038] Artemisinin (ART) was purchased from Aladdin Reagent Company.

[0039] Dihydroartemisinin (DHA) synthesis: Artemisinin (5.0 g, 18 mmol) was dissolved in anhydrous methanol (120 mL), placed in an ice-water bath, and NaBH was added in batches under stirring 4 (1.0g, 27mmol), the addition was completed within 20min. After the reaction was completed for about 2 hours, adjust the pH to 6-7 with glacial acetic acid, evaporate most of the methanol, add water and stir for 15 minutes, filter, collect the precipitate, wash with water three times, and dry to obtain a white solid (3.0 g, 59%). 1 H NMR (400MHz, CDCl 3 )δ5.59(s,1H),5.36(s,1H),5.29(s,1H),4.72(t,J=8.8Hz,1H),3.45(d,J=8.6Hz,1H),3.19( s,1H),2.57(d,J=3.4Hz,1H),2.41-2.23(m,3H),2.06-1.96(m,2H),1.40(s,3H),1.39(s,3H),0.93 (s,6H),0.92(s,3H),0.91(s,3H); 13 CNMR (100...

Embodiment 2

[0049] Example 2 provides the preparation method of 5b in the above synthetic route, X in formula I is methylene, and n=1.

[0050] In this example, the synthesis of dihydroartemisinin (DHA) is the same as that in Example 1, and will not be repeated in this example.

[0051] Synthesis of compound (1b): Dihydroartemisinin (840mg, 3.0mmol) and 3-bromo-1-propanol (0.42mL, 4.6mmol) were dissolved in CH at below 0°C 2 Cl 2 (20mL), add BF dropwise 3 ·Et 2 O (0.63mL, 5.0mmol), continued to stir at the same temperature for 5min after the dropwise addition was completed, then transferred to an ice-water bath, and continued to stir for about 50min. After the reaction was completed, the saturated NaHCO 3 Solution, water and saturated brine were washed, the organic layer was collected, dried over anhydrous sodium sulfate, and concentrated to obtain a light yellow oily crude product. The crude product was separated by silica gel chromatography (ethyl acetate:petroleum ether=3:97) to o...

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Abstract

The invention relates to the field of medicine, in particular to artemisinin derivatives containing isothiocyanate group and application thereof, namely artemisinin-isothiocyanate derivatives that mayrelease hydrogen sulfide messenger molecules in a body. Two types of derivatives are provided according to an embodiment; artemisinin and NCS (isothiocyanate) group are linked via an ether(ester) bridge chain, the multi-target glioma treatment action is given to play, and accordingly, small-molecular drugs effective to treat gliomas are acquired. The artemisinin derivatives are suitable for the preparation of anti-glioma drugs and have higher cytotoxicity for malignant gliomas U87 and U251 than dihydroartemisinin.

Description

technical field [0001] The invention relates to the field of medicine, in particular to an artemisinin derivative containing an isothiocyanate group and an application thereof. Background technique [0002] Malignant glioma is the most common intracranial malignant tumor, which is characterized by rapid growth, strong invasiveness, easy recurrence after surgery, and high mortality. After years of hard work, the death rate and disability rate are still high. Although surgical treatment has significantly improved the survival of glioma patients, drug therapy is still one of the important means of treating glioma due to the difficulty of radical cure. Research and development of new chemotherapeutic drugs is an important way to control the progression of the disease. Contents of the invention [0003] The object of the present invention is to provide an isothiocyanate group-containing artemisinin derivative and its application, which aims to provide a new composition, which ...

Claims

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Application Information

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IPC IPC(8): C07D493/20A61P35/00
Inventor 何细新皮荣标黎明涛钟晓琳罗慧娟王佳敏
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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