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Sparganiaceae lactone B derivative as well as preparation method and use thereof

A technology of black triangular lactone and derivatives, which is applied in the fields of chemical and pharmaceutical invention, can solve the problems of difficulty in extraction and separation, source limitation, low natural content of black triangular lactone B, etc., and achieves simple preparation method, easy operation, The effect of high tumor cell growth inhibitory activity

Inactive Publication Date: 2015-06-24
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The natural content of black trilendolide B is low, the extraction and separation are difficult, and its source is greatly restricted

Method used

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  • Sparganiaceae lactone B derivative as well as preparation method and use thereof
  • Sparganiaceae lactone B derivative as well as preparation method and use thereof
  • Sparganiaceae lactone B derivative as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Add 50 mg of black trigonalide B to methanol solution of ammonia gas (self-made, about 10 mol / L, 2 mL), reflux for 8 h, evaporate the solvent to dryness under reduced pressure, and separate by column chromatography (eluent is petroleum ether / ethyl acetate Ester = 3 / 1) to obtain 141 mg of the compound as a yellow solid, with a yield of 82%. 1 H NMR(400MHz,DMSO)δ12.32(s,1H),11.72(s,1H),9.37(s,1H),7.40(s,1H),7.21(d,J=8.7Hz,1H),7.11 (s,1H),6.91(d,J=8.7Hz,1H),6.81(d,J=8.2Hz,1H),6.71(d,J=8.6Hz,1H); 13 C NMR (400MHz, DMSO) δ163.3, 157.1, 152.7, 143.4, 141.2, 126.8, 123.9, 122.2, 119.7, 118.9, 118.3, 116.3, 108.8, 108.3, 106.6; HRMS: C 15 h 9 o 4 N[M+Na] + The theoretical value of m / z is 290.0424, and the measured value is 290.0431.

Embodiment 2

[0025]

[0026] Add 50 mg of black trigonalide B to an ethanol solution of methylamine (31-35%, 2 mL), and follow the method of Example 1 to obtain 245 mg of compound, a yellow solid, with a yield of 86%. 1 H NMR(400MHz,DMSO)δ12.29(s,1H),9.42(s,1H),7.74(s,1H),7.17(d,J=8.7Hz,1H),7.08(d,J=2.2Hz ,1H),6.91(d,J=8.8Hz,1H),6.80(d,J=8.7Hz,1H),6.72(dd,J=8.8,2.2Hz,1H),3.52(s,3H); 13 C NMR (400MHz, DMSO) δ171.5, 159.6, 147.7, 145.6, 143.7, 135.7, 128.4, 125.1, 121.2, 119.2, 119.4, 117.0, 113.8, 108.6, 105.6, 36.9; HRMS: C 16 h 11 o 4 N[M+Na] + The theoretical value of m / z is 304.0580, and the measured value is 304.0589.

Embodiment 3

[0028]

[0029] Add n-butylamine (21 mg) to the isopropanol solution of black trilendolide B (50 mg), and follow the method of Example 1 to obtain 347 mg of the compound as a light yellow solid with a yield of 78%. 1 H NMR(400MHz,DMSO)δ12.36(s,1H),9.38(s,1H),7.78(s,1H),7.21(d,J=8.7Hz,1H),7.16(d,J=2.4Hz ,1H),6.92(d,J=8.8Hz,1H),6.82(d,J=8.8Hz,1H),6.73(dd,J=8.8,2.6Hz,1H),3.97(t,J=7.3Hz ,2H),1.77–1.67(m,2H),1.35(dd,J=14.7,7.7Hz,2H),0.94(t,J=7.4Hz,3H); 13 C NMR (400MHz, DMSO) δ170.1, 158.9, 150.6, 144.2, 140.1, 127.8, 126.4, 123.3, 119.8, 118.0, 117.5, 117.0, 111.5, 110.3, 106.2, 45.4, 30.2, 20.7, 14.2; HRMS: C 19 h 17 NO 4 [M+Na] + The theoretical value of m / z is 346.1050, and the measured value is 346.1055.

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Abstract

The invention relates to a natural product sparganiaceae lactone B derivative as well as a preparation method and use for preparing anti-tumor drugs. The structural formula of the derivative is show in the description, wherein R is hydrogen, C1-6 alkyl, C3-6 cycloalkyl, C5-10 aryl, pyridyl, CnH2nX, OR1 or NR2R3; n is 1-6, X is vinyl, acetenyl, C5-10 aryl, azo-aryl containing 1-4 nitrogen atoms and 1-5 carbon atoms, hydroxyl, C1-4 alkoxyl, amino, N, N-biC1-4 alkyl amino, carboxyl, acylamino, sulphonylamino, C1-4 alkoxycarbonyl, cyano or nitryl; R1 is hydrogen, C1-4 alkyl, benzyl or methoxyl benzyl; and R2 and R3 are respectively hydrogen, C1-4 alkyl, benzyl, methoxyl benzyl or R2 and R3 jointly form a 4-7 membered ring with N atoms. The sparganiaceae lactone B derivative provided by the invention is used for anti-tumor drugs, and the compound provided by the invention is novel in structure, has relatively good druggability and relatively high activity of inhibiting tumor cell growth, and is simple and convenient in preparation method and easy to operate and amplify.

Description

technical field [0001] The invention belongs to the technical field of chemical and pharmaceutical inventions, and in particular relates to black trilendolide B derivatives and their preparation methods and uses. Background technique [0002] The tuber of Sparganium stoloniferum Buch-Ham, which is a plant of the family Black Sparganaceae, is the peeled and dried tuber of Sparganium stoloniferum Buch-Ham, a traditional Chinese medicine. Gas elimination and other effects. Liang Qiaoli and others discovered a new type of black xanthene-like sparstolonin B (Sparstolonin B) in Sanleng, and it has anti-atherosclerotic effect (Chinese patent, CN101899054A), in-depth molecular biology Scientific studies have shown that black trilendolide B is a TLR 2 and TLR 4 Selective antagonists (Qiao li Liang et al., Journal of biological chemistry, 286(30), 26470-26479), have strong anti-inflammatory and immunostimulatory inhibitory effects, and can be used to alleviate ischemia-reperfusion,...

Claims

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Application Information

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IPC IPC(8): C07D491/06A61P35/00
CPCC07D491/06
Inventor 孙健王超
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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