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Hesperetin quinoline hydrazone derivative with anti-tumor activity as well as preparation method and application thereof

A technology of hesperetin and quinoline hydrazone is applied to hesperetin quinoline hydrazone derivatives, preparation methods and application fields thereof, and achieves the effects of improving antitumor activity, broadening action targets, and broadening action mechanisms

Active Publication Date: 2021-12-03
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the synthesis of hesperetin hydrazone derivatives from hesperetin and hydrazinoquinoline, so it is of great significance to the design and synthesis of naringenin-4-quinoline hydrazone and the study of antitumor activity

Method used

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  • Hesperetin quinoline hydrazone derivative with anti-tumor activity as well as preparation method and application thereof
  • Hesperetin quinoline hydrazone derivative with anti-tumor activity as well as preparation method and application thereof
  • Hesperetin quinoline hydrazone derivative with anti-tumor activity as well as preparation method and application thereof

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Experimental program
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Embodiment 1

[0033] Hesperetin-4-quinoline hydrazone, the molecular formula is C 25 h 21 N 3 o 5 , the molecular structure formula is:

[0034]

[0035] The preparation method of hesperetin-4-quinoline hydrazone comprises the following steps:

[0036] (1) Dissolve 20 mmol 2-chloroquinoline in absolute ethanol, add 8 mL of hydrazine hydrate (in excess) with a mass fraction of 80%, and react at reflux temperature for 8 hours to obtain a crude intermediate;

[0037] (2) The intermediate crude product is recrystallized with absolute ethanol to obtain an orange flaky crystal 2-hydrazinoquinoline intermediate;

[0038] (3) Dissolve 12mmol of 2-hydrazinoquinoline intermediate and 10mmol of hesperetin in absolute ethanol respectively, mix them, add 2 to 5 drops of glacial acetic acid to catalyze, react at reflux temperature, and monitor the reaction progress with TLC, and proceed with the reaction. Precipitate orange precipitate;

[0039] (4) After the reaction is finished, suction filter...

experiment example

[0044] The present invention is used for in vitro antitumor activity experiment, and assay method (MTT method) is as follows:

[0045] 1. Cell culture

[0046] The human gastric cancer cell BGC-823, human liver cancer cell BEL-7402, human lung cancer cell A549 and human breast cancer cell MCF-7 selected for this experiment need to be treated with 1% (v / v) double antibiotics (100 U / mL chain Mycin and 100 U / mL penicillin), 89% (v / v) 1640 basal medium and 10% (v / v) fetal bovine serum complete medium. at 37°C with 5% CO 2Cultured in an incubator, the medium was changed on the second day, and passaged on the third day. The experimental study took the cells that grew stably in the logarithmic phase.

[0047] 2. Cell passage

[0048] Observe the density of the cells. When the cells proliferate to about 80%, discard the original culture medium, add sterile PBS solution to wash 1-2 times, add 0.25% trypsin, digest for 5 minutes, add complete medium, blow the cells gently, Collect t...

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Abstract

The invention discloses a hesperetin quinoline hydrazone derivative with anti-tumor activity as well as a preparation method and application thereof. The molecular formula of the hesperetin quinoline hydrazone derivative is C25H21N3O5. The antitumor activity of the hesperetin-4-quinoline hydrazone derivative is researched by adopting an MTT method; experimental results show that the derivative has an inhibition effect on proliferation of human gastric cancer cells BGC-823, human hepatoma carcinoma cells BEL-7402, human lung cancer cells A549 and human breast cancer cells MCF-7; compared with the activity of hesperetin, the activity of the hesperetin quinoline hydrazone derivative is improved by 2-4 times unequally, so that the activity is greatly enhanced, and particularly, the derivative is more sensitive to BEL-7402 cells, and the IC50 value is 10.97 [mu]M; and it is indicated that the hesperetin-4-quinoline hydrazone has a good inhibition effect on four experimental tumor cells, the inhibition activity of the hesperetin-4-quinoline hydrazone is higher than that of a corresponding raw material medicine hesperetin, especially the inhibition effect of the hesperetin-4-quinoline hydrazone on human liver cancer cells BEL-7402 has good selectivity, the inhibition activity is improved by nearly 4 times, and the derivative is an antitumor compound with a very good application prospect.

Description

technical field [0001] The invention relates to a hesperetin quinoline hydrazone derivative with antitumor activity and a preparation method and application thereof, belonging to the field of medicine. Background technique [0002] Hesperetin is a dihydroflavonoid compound, which is widely distributed in the plant kingdom and has various biological activities such as anti-tumor, anti-oxidation, lowering cholesterol, treating diabetes, and protecting cardiovascular, but its water solubility is poor, resulting in low bioavailability , so its structural modification to obtain high-efficiency, low-toxicity, and good-solubility drug molecules has always been the focus of many researchers. At present, the structural modification of hesperetin derivatives with anti-tumor activity mainly focuses on hydroxymethylation, etherification, esterification, halogenation, carbonyl acylation, etc. Pyrimidine hydrazone anti-tumor derivatives have not been reported in the relevant literature. ...

Claims

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Application Information

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IPC IPC(8): C07D405/12A61P35/00
CPCC07D405/12A61P35/00
Inventor 苑娟李恺昊兰海荣曾岱褚意新
Owner HENAN UNIV OF CHINESE MEDICINE
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