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Flavonoid aromatase inhibitor and its preparation method and application

An aromatase and inhibitor technology, used in organic chemistry, anti-tumor drugs, drug combinations, etc., can solve problems such as low selectivity and poor efficacy

Active Publication Date: 2020-01-31
TIANJIN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its efficacy is not superior to that of tamoxifen, and the main problem is still that the selectivity is not too high, and other second-generation aromatase inhibitors have not been approved for clinical application

Method used

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  • Flavonoid aromatase inhibitor and its preparation method and application
  • Flavonoid aromatase inhibitor and its preparation method and application
  • Flavonoid aromatase inhibitor and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 1. Synthesis and aromatase inhibitory activity of 2-(4-(7-(cyanomethyloxy)-4-oxo-4H-benzopyrone-3-yl)phenoxy)acetonitrile

[0046] 2. Preparation of 2-(4-(7-(cyanomethyloxy)-4-oxo-4H-benzopyrone-3-yl)phenoxy)acetonitrile

[0047] Take a dry 50mL round bottom flask, weigh 7-hydroxy-3-(4-hydroxyphenyl)-4H-benzopyran-4-one (didzein, 0.2543g, 1mmol) into it, and then add dropwise N,N'-Dimethylformamide (DMF, 3mL) was placed in a bottle, stirred at room temperature for 5min, then weighed sodium hydride (0.0480g, 2mmol) and added to the reaction solution, and continued to stir until no more Saturated with gas, then added chloroacetonitrile (503 µL, 4 mmol) dropwise at room temperature, added chloroacetonitrile (76 µL, 1 mmol) after 30 min of reaction, put the reaction bottle in an oil bath at 61 °C and continued to stir, then reacted for 13 hours , TLC monitoring, until the reaction of raw materials is complete. Transfer the reaction solution to a 500mL beaker, add 300mL of...

Embodiment 2

[0075] Synthesis and aromatase inhibitory activity of 2-(5-hydroxy-2-phenyl-4H-benzopyrone-7-oxy)acetonitrile

[0076] Preparation of 2-(5-hydroxy-2-phenyl-4H-benzopyrone-7-oxy)acetonitrile

[0077] Take a dry 50mL round bottom flask, weigh 5,7-dihydroxy-2-phenyl-4H-benzopyrone-4-one (chrysin, 0.2543g, 1 mmol) into it, and then drop N,N'-Dimethylformamide (DMF, 3mL) was placed in a bottle, stirred at room temperature for 5min, then weighed sodium hydride (0.0480g, 2mmol) and added to the reaction solution, and continued to stir until no more Saturated with gas, then added chloroacetonitrile (503 µL, 4 mmol) dropwise at room temperature, added chloroacetonitrile (76 µL, 1 mmol) after 30 min of reaction, put the reaction bottle in an oil bath at 61 °C and continued to stir, then reacted for 13 Hours, TLC monitoring, until the reaction of raw materials is complete. Transfer the reaction solution to a 500mL beaker, add 300mL of distilled water and stir with a glass rod, then add...

Embodiment 3

[0083] 2-((2-(4-(cyanomethyloxy)-3-hydroxyphenyl)-5-hydroxy-4-oxo-4H-benzopyrone-7-yl)oxy)acetonitrile synthesis and aromatase inhibitory activity

[0084] Preparation of 2-((2-(4-(cyanomethyloxy)-3-hydroxyphenyl)-5-hydroxy-4-oxo-4H-benzopyrone-7-yl)oxy)acetonitrile

[0085] Take a dry 50mL round bottom flask, weigh 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyrone-4-one (luteolin, 0.2862g, 1 mmol) into it, then drop N,N'-dimethylformamide (DMF, 3mL) into the bottle, stir at room temperature for 5min, then weigh sodium hydride (0.0480g, 2mmol) into the reaction solution Continue to stir until no more gas comes out, then add chloroacetonitrile (503µL, 4mmol) dropwise at room temperature, add chloroacetonitrile (76µL, 1mmol) after 30min reaction, put the reaction bottle in a 61℃ Stirring was continued in the oil bath, followed by reaction for 13 hours, monitored by TLC, until the reaction of the raw materials was complete. Transfer the reaction solution to a 500mL beaker, ...

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Abstract

The invention relates to a flavonoid aromatizing enzyme inhibitor. Through cyanomethylation reaction and alkylation reaction, some substituted groups on the mother ring of a flavonoid compound are changed and a series of flavonoid compounds and derivatives thereof are synthesized. The structural general formula can be shown in the general formula in claims. In the structural general formula, R1 isselected from any one of -OH or -H, R2 is selected from any one of -H, -OCH3 or -OH, R3 is selected from any one of -H, -OH, -OCH2CN or -OCH3, R4 is selected from any one of -H, -OH, -CH2Ph or -2-(2-methoxy-2-oxo ethyl)benzyloxy, R5 is selected from any one of -H, -OCH2Ph or -OCH3, and R6 is selected from any one of -H, -OH or -OCH3. The flavonoid compounds have good inhibition effect on aromatizing enzyme; through activity test, the maximal value IC50 of inhibiting the activity of the aromatizing enzyme by the inhibitor is equal to 0.251 [mu]mol / L.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and relates to enzyme inhibitors, in particular to a flavonoid aromatase inhibitor and its preparation method and application. Background technique [0002] Aromatase (CYP19) belongs to the cytochrome P450 family. It is an enzyme protein composed of 503 amino acids. It is composed of hemoglobin and lutein protein. It is widely found in normal tissues such as ovary, placenta, testis, brain, fat, and bone. In organs, it is expressed in the endoplasmic reticulum membrane of cells and tightly combined with the membrane. It is highly expressed in placenta and ovarian follicular granulosa cells, and in non-glandular bodies such as subcutaneous fat, muscle, liver, brain, normal breast interstitium and breast cancer. There is also low level expression in tissues. 80% of postmenopausal breast cancer patients with estrogen receptor (ER) positive have aromatase activity in tumor tissue. The active ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/36C07D311/30A61P35/00
CPCC07D311/30C07D311/36
Inventor 戴玉杰孟繁哲刘艳春耿艺超芦魁张黎明
Owner TIANJIN UNIV OF SCI & TECH
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