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Flavonoid derivative with tumor cell inhibition and preparation method and application thereof

A technology of tumor cells and derivatives, applied in antineoplastic drugs, medical preparations containing active ingredients, organic chemistry, etc., can solve problems such as side effects, intolerance and drug resistance, and failure to reduce postoperative recurrence and metastasis , to achieve good anti-proliferation activity and high anti-tumor activity

Active Publication Date: 2019-09-17
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Current cancer treatments are mainly surgery, chemotherapy, and radiation therapy, which cannot reduce postoperative recurrence and metastasis, and show their limitations and disadvantages, such as serious side effects, increased intolerance, and drug resistance

Method used

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  • Flavonoid derivative with tumor cell inhibition and preparation method and application thereof
  • Flavonoid derivative with tumor cell inhibition and preparation method and application thereof
  • Flavonoid derivative with tumor cell inhibition and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0017] (1) Synthesis of compound 1a: at room temperature, 2,4,6-trihydroxyacetophenone 1 (1.0 equivalents) and K 2 CO 3 (2.0 equivalents) was dissolved in acetone and dropped into Me 2 SO 4 (2.0eq), the temperature was raised to 40° C., and the reaction was monitored by TLC for about 4 hours. The reaction was filtered and washed 3 times with acetone. Evaporation of the organic phase afforded 1a in 98% yield.

[0018] (2) Synthesis of compound 2b: 3,5-dimethyl p-hydroxybenzaldehyde (6mmol, 1.0eq), K 2 CO 3 (12mmol, 2.0eq) was dissolved in anhydrous DMF (40mL), cooled to 0 degrees. Then BrBn (6.6mmol, 1.1eq) was added dropwise, and after the drop, the temperature was slowly raised to room temperature. The reaction was monitored by TLC. After the reaction was completed, 50 mL of water was added, extracted with EA 20 mL×3, the organic layers were combined, washed three times with 50 mL of water, washed three times with 20 mL of saturated saline, and washed three times with a...

Embodiment 2

[0025] In order to further confirm the accuracy of the compound structure, nuclear magnetic resonance was used to detect the target product 6-1-6-14 compound to obtain the following results:

[0026] Compound 6-1: 60% yield, m.p.: 134.3-135.7℃, 1 HNMR (400MHz, CDCl 3 )δ: (ppm) 7.49 (s, 2H, Ar-H), 6.56 (s, 2H, Ar-H, C=C-H), 6.35 (s, 1H, Ar-H), 4.26 (s, 1H, NH ),3.94(s,5H,OCH 3, COCH2),3.91(s,3H,OCH 3 ),3.77(s,3H,OCH 3 ),2.38(s,6H,ArCH 3 ); 13 C NMR (151MHz, CDCl 3 )δ: (ppm) 177.7, 172.4, 163.8, 161.1, 160.8, 159.9, 148.9, 127.6, 126.8, 123.7, 109.2, 107.4, 96.0, 92.8, 56.4, 55.7, 52.4, 49.3, 19.1. C 22 h 24 o 6 N,[M+H] + m / z: 398.1598, found: 398.1596.

[0027] Compound 6-2: 55% yield, m.p.: 192.7-193.3°C; 1 HNMR (400MHz, CDCl 3 )δ: (ppm)7.47((s,2H,Ar-H),6.55-6.56(m,1H,Ar-H,C=C-H),6.34(d,J=2.0Hz,1H,Ar-H) ,6.36(d,J=2.0Hz,1H,Ar-H),4.10-4.15(m,1H,NH CH ),3.93(s,3H,OCH 3 ),3.90(s,3H,OCH 3 ),3.61(s,3H,OCH 3 ),2.36(s,6H,ArCH 3 ),1.61-1.80(m,3H,CH 2 CH), 0.97(t, J...

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Abstract

The invention relates to a flavonoid derivative and a preparation method and application thereof. A coupling reaction is used to prepare the flavonoid derivative, 4'-OH is replaced with an amino substituted substance, and a nitrogen-containing derivative is synthesized on a flavonoid skeleton. By introducing the amino substituted substance, hydrogen bonding of the flavonoid derivative and a target protein can be regulated, and at the same time, an ester water partition coefficient can be also regulated, so that the flavonoid derivative can pass a blood-brain barrier relatively well, and thereby plays a role in inhibiting tumor cells. An anti-proliferative activity research of the flavonoid derivative in tumor cells HEL and PC3 is studied by MTT assay, results show that the flavonoid derivative has good anti-proliferative activity against the tumor cells HEL and PC3, and has higher antitumor activity than natural flavonoid apigenin, and the anti-proliferative effect of the flavonoid derivative is similar to that of clinical anti-tumor drug cisplatin.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a flavone derivative capable of inhibiting tumor cells, a preparation method and application thereof. Background technique [0002] Cancer is considered to be the leading cause of death in the 21st century and the most important obstacle to increasing life expectancy. There were an estimated 18.1 million new cases and 9.6 million cancer deaths worldwide in 2018. This number will increase over time. Current cancer treatments are mainly surgery, chemotherapy, and radiotherapy, which cannot reduce postoperative recurrence and metastasis, and show their limitations and disadvantages, such as severe side effects, increased intolerance, and drug resistance. Therefore, the need to develop a series of new anticancer drugs is increasing. [0003] Flavonoids are polyphenolic secondary metabolites extracted from plants and fungi that possess diverse biological activities, espe...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/352A61P35/00
CPCC07D311/30A61P35/00Y02P20/55
Inventor 陈超潘卫东李珂张妮任海宋俊荣
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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