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Caffeic acid p-nitrophenyl ethyl ester as well as preparation method and application of caffeic acid p-nitrophenyl ethyl ester

A technology of nitrophenethyl ester and caffeic acid, applied in the fields of chemistry and pharmacy, can solve the problems of uncertain curative effect, obvious side effects, high price and the like, and achieve the effects of increasing the number of peripheral blood white blood cells, good curative effect and low cost

Inactive Publication Date: 2013-06-12
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly has the following problems: the curative effect of the existing leukocyte-increasing drugs is not sure; while component blood transfusion and hematopoietic stimulating factors are effective, but the action time is short, easy to repeat, side effects are obvious, and the price is expensive, and the financial burden on patients is relatively large
Caffeic acid phenethyl ester (CAPE) is a main active component in propolis, which has anti-tumor, anti-oxidation, anti-inflammation, immune regulation and other pharmacological effects, but whether it can increase white blood cells has not been published at home and abroad to report

Method used

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  • Caffeic acid p-nitrophenyl ethyl ester as well as preparation method and application of caffeic acid p-nitrophenyl ethyl ester
  • Caffeic acid p-nitrophenyl ethyl ester as well as preparation method and application of caffeic acid p-nitrophenyl ethyl ester

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1, the preparation of p-nitrophenethyl caffeic acid (with 1,4-dioxane as solvent)

[0016] Put caffeic acid (1.02g, 5.6mmol) in a 50ml three-necked flask, add 25ml of 1,4-dioxane to dissolve, then add thionyl chloride (0.6ml, 8.2mmol), heat to 100°C for reflux reaction, Then 10 ml of a 1,4-dioxane solution of p-nitrophenylethanol (1.40 g, 8.4 mmol) was added dropwise, and the reflux reaction was continued, and the reaction progress was monitored by thin-layer chromatography. After the reaction was completed, the reaction liquid was naturally cooled, diluted with water, extracted 3 to 4 times with ethyl acetate, combined with the ethyl acetate extracts, dried overnight with anhydrous magnesium sulfate, filtered with suction, and the filtrate was distilled off under reduced pressure to obtain yellow Brown liquid, separated and purified by column chromatography (silica gel 200~300 mesh), using ethyl acetate-petroleum ether (volume ratio 1:2) mixed solvent as t...

Embodiment 2

[0017] Embodiment 2, the preparation of p-nitrophenethyl caffeic acid (with acetonitrile as solvent)

[0018] Put caffeic acid (1.02g, 5.6mmol) in a 50ml three-neck flask, add 25ml of acetonitrile to dissolve, then add thionyl chloride (0.6ml, 8.2mmol), heat to 80°C for reflux reaction, then add p-nitrobenzene dropwise Ethanol (1.40g, 8.4mmol) in acetonitrile solution 10ml, continue to reflux reaction, monitor the progress of the reaction with thin layer chromatography. After the reaction was completed, the reaction liquid was naturally cooled, diluted with water, extracted 3 to 4 times with ethyl acetate, combined with the ethyl acetate extracts, dried overnight with anhydrous magnesium sulfate, filtered with suction, and the filtrate was distilled off under reduced pressure to obtain yellow Brown liquid, separated and purified by column chromatography (silica gel 200~300 mesh), using ethyl acetate-petroleum ether (volume ratio 1:2) mixed solvent as the eluent, collecting t...

Embodiment 3

[0019] Embodiment 3, the preparation of p-nitrophenethyl caffeic acid (using chloroform as solvent)

[0020] Put caffeic acid (1.02g, 5.6mmol) in a 50ml three-necked flask, add 25ml of chloroform to dissolve, then add thionyl chloride (0.6ml, 8.2mmol), heat to 65°C for reflux reaction, then add p-nitrogen dropwise Trichloromethane solution 10ml of phenylethyl alcohol (1.40g, 8.4mmol), continue to reflux reaction, monitor reaction process with thin-layer chromatography. After the reaction was completed, the reaction liquid was naturally cooled, diluted with water, extracted 3 to 4 times with ethyl acetate, combined with the ethyl acetate extracts, dried overnight with anhydrous magnesium sulfate, filtered with suction, and the filtrate was distilled off under reduced pressure to obtain yellow Brown liquid, separated and purified by column chromatography (silica gel 200~300 mesh), using ethyl acetate-petroleum ether (volume ratio 1:2) mixed solvent as the eluent, collecting th...

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Abstract

The invention belongs to the fileds of chemistry and pharmacy, in particular to caffeic acid p-nitrophenyl ethyl ester of which the structural formula is as shown in formula I. The caffeic acid p-nitrophenyl ethyl ester has the effect of increasing leukocytes, can obviously increase the number of the peripheral blood leukocytes of mice with immunosuppression caused by cyclophosphamide, can be used for preparing medicaments for increasing the white blood cells, plays an important role in treating leukopenia after radiochemotherapy on malignant tumors and possibly has a good curative effect on the leukopenia caused by other pathogenic factors. The invention also provides a preparation method of the caffeic acid p-nitrophenyl ethyl ester, which comprises the following steps: heating caffeic acid and thionyl chloride in a polar organic solvent to carry out a refluxing reaction so as to generate caffeic acid acyl chloride, adding p-nitrophenyl ethanol, continuing to heat to carry out the refluxing reaction so as to generate the caffeic acid p-nitrophenyl ethyl ester, and finally separating and purifying by column chromatography to obtain pure caffeic acid p-nitrophenyl ethyl ester. Themethod has the advantages of high yield and low cost, is convenient to operate and the like.

Description

technical field [0001] The invention relates to the fields of chemistry and pharmacy, in particular to a new compound, a preparation method of the compound and an application of the compound in pharmacy. Background technique [0002] When the number of white blood cells in peripheral blood is continuously lower than 4×10 9 / L is called leukopenia. Leukopenia is a disease caused by unknown causes and secondary to other diseases. It is divided into two types: primary and secondary: the primary cause is unknown; the secondary cause is acute infection, physical and chemical factors, blood Systemic diseases, diseases with splenomegaly, connective tissue diseases, allergic diseases, genetic diseases, acquired or unexplained neutropenia, etc. Leukopenia is a common complication in malignant tumors, especially in patients undergoing radiotherapy and chemotherapy. Because radiation and drugs inhibit bone marrow hematopoietic function, leukopenia is often caused. At present, the tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C205/42C07C201/12A61K31/216A61P7/00
Inventor 李逐波邓莉左华何小燕陈敏向春艳杨俊峰刘衍季赖翔宇
Owner SOUTHWEST UNIV
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