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Flavonoid derivatives and their preparation methods and applications

A technology of derivatives and flavones, applied in the field of flavone derivatives, can solve the problem that anticancer drugs cannot meet the ideal requirements

Active Publication Date: 2020-05-08
EFFEPHARM (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Due to the drug resistance of tumor cells and a series of adverse reactions, the existing anticancer drugs can not meet the ideal requirements

Method used

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  • Flavonoid derivatives and their preparation methods and applications
  • Flavonoid derivatives and their preparation methods and applications
  • Flavonoid derivatives and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 1.2mmol of (S)-N-methylaniline and 1mmol of 3,3,3-heptyl trifluoropyruvate to 10mL of dry THF, add molecular sieves and a catalytic amount of p-toluenesulfonic acid, reflux reaction 6- 7h, cooled, filtered, concentrated, filtered to obtain the corresponding heptyl (S)-N-methylphenyliminoate.

[0021] Add 1.0 mmol of dihydromyricetin to 5 mL THF containing 0.1 mmol of trifluoromethanesulfonic acid, stir, cool to -40°C, add 1.1 mmol of (S)-N-methylphenylimino ketone heptyl , reacted for 24h, evaporated to dryness under reduced pressure, added 10mL of dichloromethane, washed with water, concentrated, transferred to a pressure reactor, added 10mL of ethanol, and then added 0.05mmol of Pd(OH) 2 , flow hydrogen (5 bar), react at room temperature for 3 h, filter, concentrate, and purify by column chromatography to obtain the target compound (1).

[0022] Compound (1): Yield 71%; 'H NMR (DMSO-d6, 400MHz) δ: 0.97 (s, 3H), 1.33-1.57 (m, 10H), 4.11 (t, 2H), 4.42 (d, J = 11Hz...

Embodiment 2

[0024] 1.0 mmol of naringenin was used to replace 1.0 mmol of dihydromyricetin, and other operations were the same as in Example 1 to obtain compound (2).

[0025] Compound (2): Yield 68%; 'H NMR (DMSO-d6, 400MHz) δ: 0.96 (s, 3H), 1.33-1.57 (m, 10H), 2.71-3.32 (m, 2H), 4.11 (t , 2H), 5.46 (dd, J = 2.6Hz, 12.9Hz,1H), 5.89 (s, 2H), 6.80 (d, J = 8.0Hz, 2H), 7.33 (d, J = 8.0Hz, 2H), 8.91 (s,2H), 10.81 (s, 1H), 11.88 (s, 1H); ESI-MS m / z: 511[M] + .

Embodiment 3

[0027] 1.0 mmol of hesperetin was used to replace 1.0 mmol of dihydromyricetin, and other operations were the same as in Example 1 to obtain compound (3).

[0028] Compound (3): Yield 73%; 'H NMR (DMSO-d6, 400MHz) δ: 0.97 (s, 3H), 1.33-1.57 (m, 10H), 2.71-3.32 (m, 2H), 3.37 (s , 3H), 4.11 (t, 2H), 5.41 (dd, J =3.0Hz, 12.4Hz, 1H), 5.89 (s, 2H), 6.86 (m, 3H),8.91 (s, 1H), 10.81 (s, 1H),11.87 (s, 1H); ESI-MS m / z: 541[M] + .

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Abstract

The invention discloses a flavone derivative or pharmaceutically acceptable hydrate and salt thereof. The flavone derivative comprises stereisomer or tautomer. The flavone derivative has the advantages that the anti-cancer function is realized, and the flavone derivative can be applied to anti-tumor treatment medicine. The invention discloses a preparation method of flavone derivative.

Description

technical field [0001] The invention relates to flavonoid derivatives and their application in pharmacy, belonging to the technical field of medicine. Background technique [0002] Due to the drug resistance of tumor cells and a series of adverse reactions, the existing anticancer drugs cannot meet the ideal requirements. It is imminent to find anticancer drugs with high efficiency and low toxicity through different ways. Using the active ingredients of natural compounds as lead compounds to modify the structure to synthesize anticancer drugs with strong biological activity, high bioavailability and low toxicity has become a hot spot in the development of new drugs today. As an important class of natural products, flavonoids widely exist in nature. Current studies have confirmed that flavonoids have a variety of biological activities, such as biological activation of carcinogens, cell signaling, cell cycle regulation, angiogenesis, inflammatory response, anti-oxidation, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/32A61P35/00
CPCC07D311/32
Inventor 张宝华张冀男郭瑞霞史兰香刘斯婕
Owner EFFEPHARM (SHANGHAI) CO LTD