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Myricetin derivative containing piperazine amides and preparation method thereof

A technology of myricetin and amides, which is applied to the preparation of myricetin derivatives containing piperazine amides, and the application field of anti-tumor, can solve the problems of less research on the anti-tumor activity of myricetin derivatives, and achieve toxic and side effects. small effect

Active Publication Date: 2017-08-08
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of myricetin is studied on itself, but there are few studies on the structure modification of myricetin and the antitumor activity of myricetin derivatives

Method used

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  • Myricetin derivative containing piperazine amides and preparation method thereof
  • Myricetin derivative containing piperazine amides and preparation method thereof
  • Myricetin derivative containing piperazine amides and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 3-(2-(4(2-chlorophenyl)piperazinyl)-2-oxoethyl)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl )-4H-chromene-4-ketone synthesis (compound number is I 1 ), including the following steps:

[0042] (1) Synthesis of 1-(2-chlorobenzyl) piperazine:

[0043] Add 2.59g (30mmol) of anhydrous piperazine, 1.20g (30mmol) of sodium hydroxide and 25mL of absolute ethanol to a 50mL single-necked flask, stir at room temperature until it is completely dissolved, add 1.27g (10mmol) of substituted benzyl chloride, and Raise the temperature to reflux until the benzyl chloride completely disappears for about 5-7 hours. Stop the reaction, remove the solvent under reduced pressure, add water to dissolve, adjust pH>12, extract with dichloromethane (3×30mL), combine the organic layers and dry over anhydrous sodium sulfate, filter with suction, remove the solvent under reduced pressure to obtain the crude product without Purification was used directly in the next step.

[0044] (2) Synthesis of 1-(...

Embodiment 2

[0051] 3-(2-(4(2,4-dichlorophenyl)piperazinyl)-2-oxoethyl)-5,7-dimethoxy-2-(3,4,5-trimethoxy phenyl)-4H-chromen-4-ketone synthesis (compound number is I 2 ), including the following steps:

[0052] (1) Synthesis of 1-(2,4-dichlorobenzyl)piperazine:

[0053] As in step (1) of Example 1, the difference is that 2,4-dichlorobenzyl chloride is used as a raw material.

[0054] (2) Synthesis of 1-(4-(2,4-dichlorobenzyl)piperazine)-2-chloroethane-1-one:

[0055] As in step (2) of Example 1, the difference is that 1-(2,4-dichlorobenzyl)piperazine is used as a raw material.

[0056] (3) Synthesis of 3-hydroxy-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one:

[0057] As in embodiment 1 (3) step.

[0058] (4) 3-(2-(4(2,4-dichlorophenyl)piperazinyl)-2-oxoethyl)-5,7-dimethoxy-2-(3,4,5 Synthesis of -trimethoxyphenyl)-4H-chromen-4-one:

[0059] As in step (4) of Example 1, the difference is that 1-(4-(2,4-dichlorobenzyl)piperazine)-2-chloroethane-1-one is used as the raw mate...

Embodiment 3

[0061] 3-(2-(4(3-methylphenyl)piperazinyl)-2-oxoethyl)-5,7-dimethoxy-2-(3,4,5-trimethoxybenzene base)-4H-chromen-4-ketone synthesis (compound number is I 3 ), including the following steps:

[0062] (1) Synthesis of 1-(3-methylbenzyl)piperazine:

[0063] As in step (1) of Example 1, the difference is that 3-methylbenzyl chloride is used as a raw material.

[0064] (2) Synthesis of 1-(4-(3-methylbenzyl)piperazine)-2-chloroethane-1-one:

[0065] As in step (2) of Example 1, the difference is that 1-(3-methylbenzyl)piperazine is used as a raw material.

[0066] (3) Synthesis of 3-hydroxy-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one:

[0067] As in embodiment 1 (3) step.

[0068](4) 3-(2-(4(3-methylphenyl)piperazinyl)-2-oxoethyl)-5,7-dimethoxy-2-(3,4,5-trimethyl Synthesis of oxyphenyl)-4H-chromen-4-one:

[0069] As in step (4) of Example 1, the difference is that 1-(4-(3-methylbenzyl)piperazine)-2-chloroethane-1-one is used as a raw material.

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Abstract

The invention discloses a myricetin derivative containing piperazine amides. The myricetin derivative containing piperazine amides is characterized in that a general formula of the myricetin derivative is as shown in the description. In the formula, R1 represents more than one hydrogen atom, methoxy, nitryl, methyl, trifluoromethyl or halogen atoms at ortho position, meta position or para position of benzene ring. The compound has certain inhibition activity on hepG2 cells and SGC7901 cells, is low in toxicity to normal cells, and can be used for preparing anti-tumor medicines.

Description

technical field [0001] The invention relates to the technical field of chemical engineering, in particular to a preparation method of a piperazinamide-containing myricetin derivative and its application in antitumor. Background technique [0002] Tumor is a common disease with complex etiology, pathology, clinical manifestations and treatment, especially malignant tumors are a serious threat to human health. Tumor formation is a multi-factor, multi-step and multi-gene mutation process, and many chemical carcinogens are known to induce and promote tumor formation. In vitro tests have shown that myricetin has obvious inhibitory effects on various human tumor cells. [0003] Myricetin (3',4',5',3,5,7-hexahydroxyflavonol, Myricetin (Myr)), synonymous myricetin, myricetin, myricetin, is a natural flavonoid and polyphenol These compounds are usually found in the fruits, vegetables, tea and beverages we eat every day. Most exist in the form of glycosides, not in the form of free...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32A61P35/00
CPCC07D311/32
Inventor 薛伟肖维张橙李普王一会陈丽娟阮祥辉张菊平李琴吴小琼贺鸣
Owner GUIZHOU UNIV
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