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A kind of flavonoid compound and its preparation method and application

A compound and flavonoid technology, applied in the field of anti-tumor compounds, can solve the problems of poor human activity and achieve obvious anti-tumor effects

Active Publication Date: 2019-05-24
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Kerr DJ etc. (Eur J Cancer Clin Oncol, 1989,25 (9): 1271) found that synthetic flavone-8-acetic acid (FAA, A) showed excellent preclinical anti-tumor activity in mouse models, but Proved to be less active in humans in early clinical trials

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  • A kind of flavonoid compound and its preparation method and application
  • A kind of flavonoid compound and its preparation method and application
  • A kind of flavonoid compound and its preparation method and application

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preparation example Construction

[0039] The preparation method of described flavonoid compound is as follows:

[0040] First, dissolve 2-hydroxyacetophenone and N,N-dimethylformamide dimethyl acetal in dry N,N-dimethylformamide, heat the oil bath to 75°C, and stir for 4h. After extraction with ethyl acetate and separation and purification by silica gel chromatography, intermediate a was obtained. Next, the intermediate a was dissolved in dichloromethane, concentrated hydrochloric acid was added dropwise, and the reaction solution was placed in an oil bath and heated to reflux for 1 h. After extraction with dichloromethane, the organic phases were combined, washed with saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, separated and purified by silica gel chromatography to obtain intermediate b. Again, the intermediate b was dissolved in dichloromethane, hydrogen peroxide and sodium hydroxide were slowly added thereto, and stirred at 0°C. After stirring...

Embodiment 1

[0047] Embodiment 1: the synthesis of intermediate compound a (3-(dimethylamino)-1-(2-hydroxyphenyl)-2-enyl acetone)

[0048]

[0049] Dissolve 2-hydroxyacetophenone (1.00g) and N,N-dimethylformamide dimethyl acetal (1.05g) in 10mL of dry N,N-dimethylformamide, heat the oil bath to 75 ℃, stirred for 4h. After analysis by thin-layer chromatography and monitoring the reaction under ultraviolet light, cool to room temperature after completion, add water and extract three times with ethyl acetate, combine the organic layers, wash with saturated sodium chloride solution, and dry over anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure, separated and purified by silica gel column chromatography using a system of n-hexane:ethyl acetate=4:1 to obtain an orange-yellow solid with a yield of 80%.

[0050] 1 H NMR (600MHz, DMSO-d 6 ): δ14.52(s,1H),7.94(dd,J=1.8,7.3Hz,1H),7.92(d,J=12.1Hz,1H),7.36(dt,J=1.6,7.7Hz,1H) , 6.78~6.86 (m, 2H), 5.98 (d, J=1...

Embodiment 2

[0051] Embodiment 2: the synthesis of intermediate compound b (chromone)

[0052]

[0053] Compound 1 (1 g) was dissolved in 25 mL of dichloromethane, concentrated hydrochloric acid (4 mL) was added thereto, and the reaction solution was placed in an oil bath and heated to reflux for 1 h. Analyzed by thin-layer chromatography and monitored the reaction under ultraviolet light, cooled to room temperature after the reaction was completed, extracted 3 times with dichloromethane, combined the organic phases, washed with saturated sodium bicarbonate, then dried with anhydrous magnesium sulfate, concentrated under reduced pressure , separated and purified by silica gel chromatography to obtain a red solid with a yield of 90%.

[0054] 1 H NMR (600MHz, CDCl 3 )δ: 8.22(dd, J=1.4,7.9Hz, 1H), 7.86(d, J=6.0Hz, 1H), 7.64~7.71(m, 1H), 7.46(d, J=8.4Hz, 1H), 7.41 (t, J=7.6Hz, 1H), 6.35 (d, J=5.8Hz, 1H).

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Abstract

The invention relates to a flavonoid compound and a preparation method and application thereof, and relates to an antitumor compound. The flavonoid compound is applied into medicines for treating cancers, such as liver cancers, cervix uterus cancers and lung cancers. The flavonoid compound has the advantages that a compound with a full new structure is obtained, the innovation property is realized, the practicality of obvious antitumor function is realized, and the flavonoid compound can be used as potential medicines to be developed and applied.

Description

technical field [0001] The invention relates to antitumor compounds, in particular to a flavonoid compound and its preparation method and application. Background technique [0002] Malignant tumor is a common and frequently-occurring disease that seriously threatens human health. It is a major scientific research topic in the field of medical science in all countries in the world. At present, there are no satisfactory prevention and control measures. In recent years, with the development of molecular biology, immunology, cell dynamics and people's further understanding of the molecular mechanism of cancer occurrence and development, the research and development of anti-tumor drugs has shifted from traditional cytotoxic drugs to tumor-related drugs. The study of targeted drugs targeting the signaling pathway. [0003] Hypoxia Inducible Factor-1 (HIF-1) is composed of two subunits, HIF-1α and HIF-1β. Stress, as well as certain pathological processes play an important role. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/22A61P35/00
Inventor 李福男李善花郑满意梁涵王宝睿詹亚东苗佳颖
Owner XIAMEN UNIV
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