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2'-chlorine-4'- nitro flavone and derivative thereof and preparation and application of 2'-chlorine-4'- nitro flavone and derivative

A reaction and group technology, applied in the field of 2'-chloro-4'-nitroflavonoids and derivatives thereof, can solve problems such as strong drug resistance with toxic and side effects, and achieve small toxic and side effects, clear mechanism of action, and selectivity. inhibiting effect

Active Publication Date: 2012-07-18
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the disadvantages of traditional chemotherapy, such as strong toxic side effects and prone to drug resistance, it has become a consensus in the industry to find targeted anticancer drugs with high efficiency and low toxicity

Method used

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  • 2'-chlorine-4'- nitro flavone and derivative thereof and preparation and application of 2'-chlorine-4'- nitro flavone and derivative
  • 2'-chlorine-4'- nitro flavone and derivative thereof and preparation and application of 2'-chlorine-4'- nitro flavone and derivative
  • 2'-chlorine-4'- nitro flavone and derivative thereof and preparation and application of 2'-chlorine-4'- nitro flavone and derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1, synthetic 6-methyl-2 '-chloro-4'-nitroflavone (R in formula I 1 =6-CH 3 , R 2 = H, R 3 = H, R 4 = NO 2 compound of)

[0044] 100mL single-necked flask, add equimolar amounts of 5-methyl o-hydroxyacetophenone and 2-chloro-4-nitrobenzoyl chloride (50mmol each), 20mL of anhydrous acetone, 4 times the equivalent of anhydrous potassium carbonate (200mmol ), heated to reflux for 15h; after the acetone was removed by suspension evaporation, 20mL of acetic acid and 1mL of concentrated sulfuric acid (mass fraction 98%) were added, heated to reflux for 2h, and the generated inorganic salt precipitate was removed by filtration, and the filtrate was dissolved in 1mol.L -1 Adjust the pH to about 7 with NaOH, extract with ethyl acetate (2×25mL), dry over anhydrous sodium sulfate, and separate by column (ethyl acetate:petroleum ether=1:3(v / v)) to obtain pure 6-methyl- 2'-Chloro-4'-nitroflavone. Yield 62%; white solid, melting point: 179-180°C.

[0045] The struct...

Embodiment 2

[0046] Embodiment 2, synthetic 7-hydroxyl-2 '-chloro-4'-nitroflavone (R in formula I 1 =7-OH,R 2 = H, R 3 = H, R 4 = NO 2 compound of)

[0047] 100mL single-necked flask, add 50mmol 2,4-dihydroxyacetophenone and 100mmol 2-chloro-4-nitrobenzoyl chloride, 20mL anhydrous acetone, 4 times the equivalent of anhydrous potassium carbonate (200mmol), and heat to reflux for 15h; After removing acetone by suspension evaporation, add 20 mL of acetic acid and 1 mL of concentrated sulfuric acid (mass fraction 98%), heat to reflux for 2 hours, filter while hot to remove the formed inorganic salt precipitate, and cool the filtrate in a refrigerator at 4°C to obtain yellow crystal 7-hydroxy-2'- Chloro-4'-nitroflavone; or add 100mL deionized water to the filtrate to generate a yellow precipitate, filter, and wash the filter residue with ethyl acetate to obtain pure yellow solid 7-hydroxy-2'-chloro-4'-nitroflavone base flavonoids. Yield 26%; pale yellow solid, melting point > 300°C.

[0...

Embodiment 3

[0049] Embodiment 3, synthetic 5-hydroxyl-2 '-chloro-4'-nitroflavone (R in formula I 1 =5-OH,R 2 = H, R 3 = H, R 4 = NO 2 compound of)

[0050] 100mL single-necked flask, add 50mmol 2,4-dihydroxyacetophenone and 100mmol 2-chloro-4-nitrobenzoyl chloride, 20mL anhydrous acetone, 4 times the equivalent of anhydrous potassium carbonate (200mmol), and heat to reflux for 15h; After the acetone was removed by suspension evaporation, the obtained tan solid was washed with hot water to obtain 5-hydroxy-2'-chloro-4'-nitroflavone as a light yellow solid. Yield: 30%, pale yellow solid, melting point: 193-194°C.

[0051] The structural confirmation data are as follows: Ms(EI)317.03. 1 H NMR (400MHz, DMSO) δ12.39(s, 1H), 8.52(d, J=2.1Hz, 1H), 8.43-8.34(m, 1H), 8.12(d, J=8.5Hz, 1H), 7.74 (t, J=8.4Hz, 1H), 7.15(d, J=8.4Hz, 1H), 6.99-6.84(m, 2H). 13 C NMR (101MHz, DMSO) δ182.59, 161.61, 159.82, 156.16, 149.28, 136.50, 136.22, 132.88, 132.72, 125.24, 122.56, 111.91, 111.42, 110.16, 107....

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Abstract

The invention discloses a 2'-chlorine-4'- nitro flavone and a derivative thereof and a preparation method and application of the 2'-chlorine-4'- nitro flavone and the derivative thereof. The structural formula of the compound is indicated as formula 1, in the formula 1, R1 is H or one or a plurality of the following replaced groups on a benzene ring: -F, -C1, -Br, -1, -OH, -CH3, -CH2CH3, -NO2, -NH2, -OCH3 and -CF3, R2 is H, -OH, -SH, -Br or -CN; R3 is H or one or a plurality of the following replaced groups on the benzene ring: -CH3, -OCH3, -CH2CH3 and -OH; R4 is -NO2, -NH2 or the compound is a mitogen activator protein cyclin-dependent kinase inhibitor, has the capacity of selectively restraining proliferation of hepatoma carcinoma cells, has low toxicity for normal hepatic cells and has important practical value and application prospects in the fields of anti-tumor reagent preparation and the diseases of anti-microbial, anti-inflammatory, anti-rheumatoid arthritis and the like (formula 1).

Description

technical field [0001] The present invention relates to a kind of 2'-chloro-4'-nitroflavone and its derivatives as well as their preparation and application. Background technique [0002] Flavonoids are widely found in nature and are an important part of people's diet. Flavonoids contain a C6-C3-C6 carbon skeleton and belong to benzopyrans. Due to the special structure, flavonoids have a wide range of physiological activities, including anti-inflammatory, anti-estrogen, antibacterial, anti-allergic, anti-oxidation, anti-tumor, etc. At present, there are two main sources of flavonoids, one is directly extracted from natural products, and the other is synthetic flavonoids. Since the content of flavonoids in natural products is generally low and has some unfavorable pharmacological properties, independent design and synthesis of flavonoids with specific structures and special pharmacological activities has become an important means of drug design. [0003] Cancer is a diseas...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/352A61P35/00A61P35/02A61P29/00A61P31/00A61P31/12A61P39/06
Inventor 蒋宇扬金锋高丹张存龙谭春燕
Owner SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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