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A sesquiterpene lactone compound and its preparation method and its application in the preparation of drugs for preventing and treating nasopharyngeal carcinoma

A technology of ester compounds and sesquiterpenes, which is applied in the field of compounds and medicines, can solve the problems of easy metastasis and recurrence, poor patient treatment compliance, and no specific anti-nasopharyngeal carcinoma, so as to inhibit the proliferation of nasopharyngeal carcinoma cells and promote Effects of Cancer Cell Apoptosis, Migration and Invasion Inhibition

Active Publication Date: 2021-07-13
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although concurrent chemoradiotherapy based on cisplatin is the standard treatment for nasopharyngeal carcinoma, more than two-thirds of nasopharyngeal carcinoma patients are already in locally advanced stage at the time of diagnosis due to the hidden location of nasopharyngeal carcinoma, which is prone to metastasis and The characteristics of relapse, and the severe side effects caused by cisplatin make the patient's treatment compliance poor
Nasopharyngeal carcinoma is a highly chemosensitive tumor. So far, there are no specific anti-nasopharyngeal carcinoma drugs in clinical practice, all of which are broad-spectrum anticancer drugs, including cisplatin, cyclophosphamide, nitrogen mustard and 5- Fluorouracil, etc., so there is an urgent need for highly effective and low-toxic anti-nasopharyngeal cancer drugs

Method used

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  • A sesquiterpene lactone compound and its preparation method and its application in the preparation of drugs for preventing and treating nasopharyngeal carcinoma
  • A sesquiterpene lactone compound and its preparation method and its application in the preparation of drugs for preventing and treating nasopharyngeal carcinoma
  • A sesquiterpene lactone compound and its preparation method and its application in the preparation of drugs for preventing and treating nasopharyngeal carcinoma

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Experimental program
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Effect test

Embodiment 1

[0050] Compounds XF-1 to XF-18 were prepared from Inula flower (Euphorbia antiquorum L.).

[0051] The dried inflorescences of Inula inula were extracted three times with 95% ethanol water at room temperature, each time for 72 hours, and the extract was concentrated under reduced pressure to obtain a crude extract. The crude extract was suspended in water, extracted with ethyl acetate, and concentrated under reduced pressure to obtain the ethyl acetate fraction, which was chromatographed on a silica gel column (100-200 mesh) and eluted with petroleum ether / ethyl acetate gradient (9:1, 8:2,2:1,1:2,0:1), after TLC detection, it was divided into 3 components (A-C). Part B (54 g) was subjected to reverse phase column chromatography, eluting with methanol / water (50%-100%) to obtain seven fractions Fr.B1-7. Fr.B2 was eluted with Sephadex LH-20 with dichloromethane / methanol (1:1) to obtain compounds XF-1 (120mg), XF-2 (2.3g), XF-3 (50mg), XF-4 (20mg). Fr.B3 was separated by HPLC t...

Embodiment 2

[0053] Preparation of Ergolide Derivatives XF2-1~XF2-30

[0054] Synthetic route a: at room temperature, the compound Ergolide (XF2, 10mg, 0.03mmol) and the catalytic equivalent of 10% Pd / C were dissolved in 2mL of methanol, in H 2 Under conditions, stir for 1h. The completion of the reaction was monitored by low-resolution mass spectrometry, the device was removed, Pd / C was removed by filtration with a microporous membrane, and concentrated under reduced pressure to obtain white solid XF2-1 (10 mg, 100%).

[0055] b: Dissolve the compound Ergolide (50mg, 0.17mmol) in tetrahydrofuran (2mL), stir in an ice bath, add 5e.q lithium hydroxide (20mg, 0.85mmol) dissolved in 1mL ethanol / water (1 / 1), TLC Monitor the reaction. After the reaction is complete, spin dry and add an appropriate amount of saturated saline, add concentrated hydrochloric acid dropwise in an ice bath, and precipitate a white solid Carpesiolin (XF-1, 37mg, 85%)

[0056] c: Put the compound Ergolide (20mg, 0.08m...

Embodiment 3

[0064] Prepare formula (I) earlier by the method of embodiment 1 and 2, add water for injection according to routine, fine filter, potting sterilization makes injection solution.

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Abstract

The invention discloses a sesquiterpene lactone compound, a preparation method thereof and an application in preparation of medicines for preventing and treating nasopharyngeal carcinoma. The structural formula of this sesquiterpene lactone compound is shown in formula (I): the sesquiterpene lactone compound provided by the present invention has higher antinasopharyngeal carcinoma activity, and the IC of most compounds 50 All below 10.0μM, especially, the IC of the anti-nasopharyngeal carcinoma activity of compound XF2‑30 50 up to 0.40 μM. The pharmacodynamic evaluation of the compound shows that it inhibits the proliferation of nasopharyngeal carcinoma cells, promotes the apoptosis of cancer cells, induces autophagy, and has obvious inhibitory effects on the migration and invasion of nasopharyngeal carcinoma cells. In the nasopharyngeal carcinoma xenograft experiment in nude mice, the inhibition rate at a dose of 7.5mg / kg reached 53%, equivalent to that of the positive control cisplatin (5mg / kg). The in vivo safety experiment also confirmed the safety of the compound, which can be applied For the preparation of drugs for the prevention and treatment of nasopharyngeal carcinoma.

Description

technical field [0001] The invention relates to the technical field of compounds and medicines, in particular to a sesquiterpene lactone compound and its preparation method and its application in the preparation of medicines for preventing and treating nasopharyngeal carcinoma. Background technique [0002] Nasopharyngeal carcinoma (NPC) is a common head and neck tumor in South China and Southeast Asia, and Guangdong has the highest incidence rate, so it is also called "Guangdong cancer". The occurrence of nasopharyngeal carcinoma is related to Epstein-Barr Virus (EBV) infection, environmental factors and genetic factors. Although concurrent chemoradiotherapy based on cisplatin is the standard treatment for nasopharyngeal carcinoma, more than two-thirds of nasopharyngeal carcinoma patients are already in locally advanced stage at the time of diagnosis due to the hidden location of nasopharyngeal carcinoma, which is prone to metastasis and The characteristics of relapse, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/93C07D405/12C07D417/12C07D409/12A61K31/365A61K31/443A61K31/4436A61K31/4709A61K31/498A61P35/00
CPCA61P35/00C07D307/93C07D405/12C07D409/12C07D417/12
Inventor 顾琼程燕芳尹智勇徐峻
Owner SUN YAT SEN UNIV
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