Emodin quaternary phosphonium salt derivative with antitumor activity, synthesis method therefor and application of emodin quaternary phosphonium salt derivative

A technology for antitumor activity and synthesis method, which is applied in the field of emodin quaternary phosphonium salt derivatives and synthesis thereof, and achieves the effects of mild conditions, simple synthesis method and convenient operation

Active Publication Date: 2017-08-18
FUJIAN MEDICAL UNIV
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  • Application Information

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Problems solved by technology

However, whether quaternary phosphonium salts, especially lipophilic quaternary phosphonium salts

Method used

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  • Emodin quaternary phosphonium salt derivative with antitumor activity, synthesis method therefor and application of emodin quaternary phosphonium salt derivative
  • Emodin quaternary phosphonium salt derivative with antitumor activity, synthesis method therefor and application of emodin quaternary phosphonium salt derivative
  • Emodin quaternary phosphonium salt derivative with antitumor activity, synthesis method therefor and application of emodin quaternary phosphonium salt derivative

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Experimental program
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Effect test

Embodiment 1

[0026] Synthesis of intermediate 2 (3-bromodecyloxyemodin)——(a)

[0027] Take 1.6g (5.8mmol) of emodin 1 and dissolve it in 120ml of acetone, add 800mg (5.8mmol) of anhydrous potassium carbonate, heat to reflux, and slowly add 1.30ml (5.8mmol) of 1,10 -Dibromodecane, reflux for 5h. Cool to room temperature, remove acetone by rotary evaporation, add 100ml of water and stir for 25min, filter with suction to obtain a yellow powder crude product, the yellow powder crude product is in the condition of dichloromethane:petroleum ether (v / v)=1:2 as eluent Then, silica gel column chromatography was carried out to obtain a bright yellow solid, that is, 926 mg of 3-bromodecyloxyemodin, with a yield of 32.7%. The characterization data of intermediate product 2 (3-bromodecyloxyemodin) are as follows:

[0028] 1H NMR (400MHz, CDCl3): 12.35(s, 1H, Ar-OH), 12.17(s, 1H, Ar-OH), 7.64(d, J=1.6Hz, 1H, Ar-H), 7.38(d, J=2.4Hz, 1H, Ar-H), 7.11(d, J=1.6Hz, 1H, Ar-H), 6.69(d, J=2.4Hz, 1H, Ar-H), 4....

Embodiment 2

[0030] Synthesis of intermediate product 2 (3-bromodecyloxyemodin)—(b)

[0031] Take 3.2g (11.6mmol) of emodin 1 and dissolve it in 240ml of ethylene glycol monomethyl ether, add 1600mg (11.6mmol) of anhydrous potassium carbonate, heat to reflux, and slowly add 2.60ml (11.6mmol) of ) of 1,10-dibromodecane, refluxing for 3.5h. Cool to room temperature, remove ethylene glycol monomethyl ether by rotary evaporation, add 200ml of water and stir for 35 minutes, filter with suction to obtain a yellow powder crude product, which is prepared in dichloromethane:petroleum ether (v / v)=1:1.5 Under the condition of eluent, silica gel column chromatography was carried out to obtain a bright yellow solid, that is, 1860 mg of 3-bromodecyloxyemodin, with a yield of 32.8%. The characterization data of intermediate product 2 (3-bromodecyloxyemodin) are as follows:

[0032] 1H NMR (400MHz, CDCl3): 12.35(s, 1H, Ar-OH), 12.17(s, 1H, Ar-OH), 7.64(d, J=1.6Hz, 1H, Ar-H), 7.38(d, J=2.4Hz, 1H, Ar-H),...

Embodiment 3

[0034] Synthesis of intermediate product 2 (3-bromodecyloxyemodin)——(c)

[0035]Take 2.4g (8.7mmol) of emodin 1 and dissolve it in 180ml of acetone, add 1200mg (8.7mmol) of anhydrous potassium carbonate, heat to reflux, and slowly add 1.95ml (8.7mmol) of 1,10 -Dibromodecane, reflux 4h. Cool to room temperature, remove acetone by rotary evaporation, add 150ml of water and stir for 30min, filter with suction to obtain a yellow powder crude product, the yellow powder crude product is in the condition of dichloromethane:petroleum ether (v / v)=1:1 as eluent Next, silica gel column chromatography was carried out to obtain a bright yellow solid, namely 1400 mg of 3-bromodecyloxyemodin, with a yield of 32.9%. The characterization data of intermediate product 2 (3-bromodecyloxyemodin) are as follows:

[0036] 1H NMR (400MHz, CDCl3): 12.35(s, 1H, Ar-OH), 12.17(s, 1H, Ar-OH), 7.64(d, J=1.6Hz, 1H, Ar-H), 7.38(d, J=2.4Hz, 1H, Ar-H), 7.11(d, J=1.6Hz, 1H, Ar-H), 6.69(d, J=2.4Hz, 1H, Ar-H),...

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Abstract

The invention relates to an emodin quaternary phosphonium salt derivative with antitumor activity, a synthesis method therefor and an application of the emodin quaternary phosphonium salt derivative. The emodin quaternary phosphonium salt derivative is {10-[(4,5-dihydroxyl-7-methyl-9,10-anthraquinon-2-yl)oxo]decyl}phosphonium triphenylbromide. Proven by experiments, the emodin quaternary phosphonium salt derivative plays a certain role in inhibiting leukemia cells and solid tumor cells and can be used for preparing antitumor drugs. The emodin quaternary phosphonium salt derivative with antitumor activity, the synthesis method therefor and the application of the emodin quaternary phosphonium salt derivative have the following advantages that the synthesis method for the emodin quaternary phosphonium salt derivative, disclosed by the invention, is simple and is moderate in conditions; shown by the experiments, the emodin quaternary phosphonium salt derivative plays a certain role in inhibiting tumor cells, particularly HL-60 cells, Molt-4 cells, human chronic medullary system leukemia cell line K-562 cells, PANC-1 cells, Bax-PC3 cells, human liver cancer cells HepG2 and human lung cancer cells A549; and lipophilic emodin quaternary phosphonium salts have an application prospect in becoming anticancer drugs.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to an emodin quaternary phosphonium salt derivative with antitumor activity and its synthesis method and application. Background technique [0002] Emodin is an effective active ingredient of traditional Chinese medicine rhubarb, knotweed, etc. It has broad-spectrum anticancer activity due to its planar structure and quinone structure. It has inhibitory effects on dozens of cancer cells such as leukemia, gastric cancer, liver cancer, and pancreatic cancer. It can be called a natural anti-cancer star. However, the inhibitory activity of emodin on most cancer cells is not enough to make medicine directly (IC50 is about 30-80μM), so it is inevitable to chemically modify emodin. In the early days, someone chemically modified the 6-position of emodin and introduced a long carbon chain quaternary ammonium salt. It was found that the modification can greatly improve the anti-cancer activ...

Claims

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Application Information

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IPC IPC(8): C07F9/54A61P35/00A61P35/02
CPCC07F9/5442A61K31/66A61P35/00A61P1/18Y02A50/30
Inventor 谢捷明王文峰游秀华吴水发邓翠敏王哲
Owner FUJIAN MEDICAL UNIV
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