5-hydroxy-2'-nitroaurone or 5-hydroxy-4'-nitroaurone derivatives and application thereof

A nitro and hydroxyl technology, applied in the field of medicinal chemistry, can solve problems such as not having angiogenesis at the same time

Active Publication Date: 2015-11-11
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing drugs that inhibit tumor cell growth or angiogenesis have a single effect, that is, they cannot simultaneously inhibit tumor cell proliferation and angiogenesis.

Method used

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  • 5-hydroxy-2'-nitroaurone or 5-hydroxy-4'-nitroaurone derivatives and application thereof
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  • 5-hydroxy-2'-nitroaurone or 5-hydroxy-4'-nitroaurone derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: preparation example

[0054]

[0055] Take 1.0 mmol of 5-hydroxyfuranone and 1.2 mmol of the corresponding aldehyde in 10 ml of glacial acetic acid and 4 drops of concentrated hydrochloric acid under the catalysis, stir at room temperature for 3-10 hours, and track the reaction progress by TLC. After the reaction, the reaction mixture was poured into ice water, and the precipitated solid was washed with water and then recrystallized to obtain the target product.

[0056] Compound II-V 1 HNMR data and melting points

[0057] Compound II

[0058] Melting point: >250°C. 1 HNMR (400MHz, DMSO-d 6 )δ9.90(s,1H),8.35-8.28(m,2H),8.24-8.16(m,2H),7.41(d,J=8.9Hz,1H),7.25(dd,J=8.8,2.7Hz ,1H),7.05(d,J=2.8Hz,1H),7.00(s,1H).

[0059] Compound III

[0060] Melting point: 207.3-208.8°C. 1 HNMR (400MHz, DMSO-d 6 )δ9.89(s,1H),8.23(dd,J=7.8,1.4Hz,1H),8.13(dd,J=8.2,1.3Hz,1H),7.92-7.82(m,1H),7.69(ddd ,J=8.7,7.4,1.4Hz,1H),7.36(d,J=8.8Hz,1H),7.24(dd,J=8.8,2.7Hz,1H),7....

Embodiment 2

[0065] Example 2: Inhibitory activity of compounds II-V on endothelial cells (HUVEC) and tumor cells A549, Bel-74021 and MCF-7

[0066] In a 96-well plate, 1000 HUVEC / well, 1500 MCF-7 or BEL-7402 / well, 2000 A549 / well were inoculated in 190 μL medium, and after culturing for 24 hours, 10 μL blank or different drug concentrations were added. For the test drug, there were 3 groups of parallel blanks for each concentration. After 72 hours of culture, the cells were treated with MTT reagent, and then the OD600 was measured to calculate the IC50.

[0067]

[0068]

Embodiment 3

[0070] Ordinary Transwell membrane (8 μmpore) was used for cell migration experiment, and Transwell membrane (8 μmpore) coated with Matrigel (60 μL×250 μg) was used for cell invasion experiment. A549 cells were first starved for 24 hours in a serum-free state, and then 20,000 A549 cells (200 μL) / well were inoculated in Transwell, and the Transwell was placed in a 24-well plate groove containing 600 μL medium (supplemented with 10% FBS) , 0.08 μM compound II was added to A549 cells and cultured for 24 hours. After removing the cells remaining on the upper layer of the Transwell, the Transwell was first fixed with methanol, and then stained with crystal violet. The number of cells in more than 10 regions was counted under a microscope with a magnification of 200 times, and the migration rate was calculated.

[0071] The inhibitory effect of compound II on the migration and invasion of tumor cell A549 is shown in figure 1 .

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Abstract

The invention discloses a 5-hydroxy-2'-nitroaurone or 5-hydroxy-4'-nitroaurone derivatives and application thereof, wherein the derivatives are a compound represented as the formula (I), an isomer or a pharmaceutically acceptable salt thereof. The compound is excellent in inhibition activity on endothelial cells and tumor cells comprising A549, Bel-74021 and MCF-7, and is excellent in inhibition effects on migration and invasion of the tumor cell A549.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to derivatives, stereoisomers, cis-trans isomers, or pharmaceutically effective Preparation and pharmaceutical use of acceptable salts. These compounds have the effects of inhibiting angiogenesis, killing cancer cells or inhibiting the proliferation of cancer cells, so these compounds can be used to treat and prevent tumors, rheumatoid arthritis, diabetes and obesity and other metabolic diseases, cardiovascular diseases, Reproductive system diseases, immune diseases, inflammation, including Alzheimer's disease and Parkinson's disease and other neurological disorders. Background technique [0002] Many plants, including rice, wheat, and many Chinese medicinal materials, contain a large amount of auroneoids. These compounds may not only play a role in ensuring nutrients, but also have a certain effect on preventing and treating diseases. [0003] Tumor cell proliferation is the ke...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83A61K31/343A61P35/00A61P3/06A61P3/10A61P3/04A61P9/00A61P15/00A61P37/02A61P29/00A61P25/28A61P25/16
CPCC07D307/83
Inventor 周国春徐娟娟苏进财
Owner NANJING UNIV OF TECH
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