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Sphaelactone derivatives, their pharmaceutical compositions, preparation method thereof and application thereof

A technology of derivatives and lactones, applied in the preparation of anti-cancer or auxiliary anti-cancer drugs, the field of pharmaceutical compositions for the treatment of cancer or adjuvant treatment of tumors, can solve the problems of drug resistance, insensitivity of tumor stem cells, etc., and achieve strong Inhibitory effect

Active Publication Date: 2011-11-09
ACCENDATECH +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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  • Sphaelactone derivatives, their pharmaceutical compositions, preparation method thereof and application thereof
  • Sphaelactone derivatives, their pharmaceutical compositions, preparation method thereof and application thereof
  • Sphaelactone derivatives, their pharmaceutical compositions, preparation method thereof and application thereof

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); 13C NMR (CDCl3, 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 present invention relates to sphaelactone derivatives, their pharmaceutical compositions, a preparation method thereof and application thereof, and especially relates to a sphaelactone derivative pharmaceutical compound which is represented by a formula (I) and is used for treating cancer diseases, pharmaceutical compositions containing an effective amount of the sphaelactone derivative pharmaceutical compound represented by the formula (I) and pharmaceutically acceptable carrier or pharmaceutical compositions with other anti-cancer medicine, a preparation method of a sphaelactone derivative, and application of the sphaelactone derivative in medicine, especially application in preparation of medicines for treating cancer diseases.

Description

technical field [0001] The present invention belongs to the technical field of medicines, in particular, it relates to mincolactone derivatives, a pharmaceutical composition for treating cancer or adjuvant treatment of tumors using it as an active ingredient, a preparation method thereof, and the preparation of the pharmaceutical compound and the composition for anticancer Or the application of adjuvant anticancer drugs. Background technique [0002] Tumors are a huge threat to human health. There are about 2 million cancer patients in my country, and 1.6 million new cases are diagnosed 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...

Claims

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Application Information

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IPC IPC(8): C07D307/93C07D493/10A61K31/365A61P35/00A61P35/02
Inventor 陈悦张泉翟佳黛马维维范洪霞张福武
Owner ACCENDATECH
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