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Application of sphaelactone and derivative thereof to treatment of cancers

A derivative, cancer technology, applied in the field of preparation of anti-cancer or auxiliary anti-cancer drugs, can solve the problems of drug resistance, tumor stem cell insensitivity, etc., and achieve the effect of strong inhibitory activity

Active Publication Date: 2011-02-23
合肥尚德药缘生物科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional chemotherapy drugs for tumor treatment have drug resistance problems, especially cancer stem cells are less sensitive

Method used

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  • Application of sphaelactone and derivative thereof to treatment of cancers
  • Application of sphaelactone and derivative thereof to treatment of cancers
  • Application of sphaelactone and derivative thereof to treatment of cancers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 11βH, the preparation of 13-dimethylaminomildolactone (compound 1, structural formula as following formula (II))

[0040]

[0041] Michelactone (106mg, 0.40mmol), triethylamine (2.0mL), and methanol (30mL) were added to a 100mL round-bottomed flask, heated to reflux for 3 hours, concentrated under reduced pressure, and silica gel column chromatography (petroleum ether: ethyl acetate Ester: triethylamine=50:50:0.5) to obtain 107.4 mg of white solid, yield: 86%.

[0042] Molecular formula: C 17 h 27 NO 3

[0043] Molecular weight: 293

[0044] Appearance: white amorphous powder

[0045] Spectral data:

[0046] 1 H NMR (CDCl 3 , 400MHz) δ3.76(t, J=10.0Hz, 1H), 2.96(s, 1H), 2.49-2.67(m, 3H), 2.28-2.34(m, 1H), 2.30-2.34(m, 2H) , 2.18(s, 6H), 2.09(brs, 2H), 1.96(d, J=11.2, 1H), 1.67-1.73(m, 2H), 1.60(s, 3H), 1.22(brs, 3H), 1.18 (br s, 2H); 13 C NMR (CDCl 3 , 100MHz) δ177.0, 131.8, 131.3, 84.0, 80.2, 58.3, 58.1, 50.9, 46.0, 44.6, 38.4, 35.3, 30.0, 27.2, 23.7, 22...

Embodiment 2

[0048] Preparation of 4-propionyl michelolactone (compound 2, structural formula as following formula (III))

[0049]

[0050] Michelolactone (106mg, 0.40mmol), triethylamine (2.0mL), propionyl chloride (0.2mL), and 5mL dichloromethane were added to a 20mL round-bottomed flask, stirred at room temperature for 24h, concentrated under reduced pressure, and silica gel column layer Analysis (petroleum ether: ethyl acetate = 90:10) gave 87 mg of white solid, yield: 72%. Structural data of the prepared 4-propionylmiglianolide:

[0051] Molecular formula: C 18 h 24 NO 4

[0052] Molecular weight: 304

[0053] Appearance: white amorphous powder

[0054] Spectral data:

[0055] 1 H NMR (CDCl 3 , 400MHz) δ6.14(s, 1H), 5.42(s, 1H), 3.74(t, J=10.0Hz, J=10.0Hz, 1H), 1.80-2.74(m, 12H), 1.67(s, 3H ), 1.50(s, 3H), 1.07(t, J=4.0Hz, 3H); 13 C NMR (CDCl 3 , 100MHz) δ173.8, 170.1, 139.5, 131.5, 130.4, 118.6, 88.4, 83.0, 56.6, 50.1, 36.5, 34.9, 30.4, 28.7, 25.9, 24.1, 18.8, 9.1.

Embodiment 3

[0057] 1, the synthetic method of 1,10-epoxy michelolactone (compound 3, structural formula following formula (IV)):

[0058]

[0059] Michelactone (106mg, 0.40mmol), m-chloroperoxybenzoic acid (0.45mmol), and 5mL of dichloromethane were added to a 20mL round-bottomed flask, stirred at room temperature for 6h, concentrated under reduced pressure, and silica gel column chromatography (petroleum ether : ethyl acetate=80:20), to obtain 96 mg of white solid, yield: 91%. Structural data of the prepared 1,10-epoxy michelolactone:

[0060] Molecular formula: C 15 h 20 NO 4

[0061] Molecular weight: 264

[0062] Appearance: white amorphous powder

[0063] Spectral data:

[0064] 1 H NMR (CDCl 3 , 400MHz) δ6.13(d, J=3.2Hz, 1H), 5.44(d, J=2.8Hz, 1H), 3.73(t, J=10.4Hz, 1H), 1.30-2.46(m, 11H), 1.29(s, 3H), 1.28(s, 3H); 13 C NMR (CDCl 3 , 100MHz) δ168.7, 137.8, 118.6, 79.2, 77.3, 74.2, 66.7, 52.6, 48.4, 37.1, 33.8, 29.0, 24.6, 22.5, 21.3.

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Abstract

The invention relates to application of sphaelactone and a derivative thereof to the treatment of cancers, in particular to application of a medicinal composition of the sphaelactone shown as a formula (I) and the derivative thereof to the treatment of the cancers, a medicinal composition which contains a therapeutically effective amount of a compound (I) and a pharmaceutically acceptable carrier, or a composition of the medicinal composition and other anti-cancer medicaments, a preparation method of the sphaelactone derivative, and application of the sphaelactone and the derivative thereof to medicaments, particularly the preparation of the medicaments for treating the cancers.

Description

technical field [0001] The present invention belongs to the technical field of medicines, and in particular relates to the use of mimilactone and its derivatives in treating cancer or adjuvantly treating tumors, and their application in preparing anticancer or adjuvant anticancer drugs. Background technique [0002] Tumors are a great threat to human health. There are about 2 million cancer patients in my country, with 1.6 million new cases every year. This is a large group. Anti-tumor research is a very challenging and significant field in the field of life sciences today. . In the past, the treatment methods focused on the eradication and killing of cancer cells. At present, the commonly used antineoplastic drugs in clinical practice are mainly cytotoxic drugs. These anticancer drugs have disadvantages such as poor selectivity, strong toxic and side effects, and easy drug resistance. , is a typical double-edged drug, and it is difficult to eradicate cancer, and many cancer...

Claims

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Application Information

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IPC IPC(8): A61P35/00A61K31/365
Inventor 陈悦张泉卢亚欣丁亚辉翟佳黛马维维范洪霞张浩亮王淼
Owner 合肥尚德药缘生物科技有限公司
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