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Phenyl nitrone compounds containing stilbene sections and application thereof

The technology of a compound and nitrone, which is applied in the preparation of anti-tumor drugs, the preparation of the compounds, and the field of neuroprotective agents, can solve problems such as hindering the clinical application of targeted anti-tumor drugs.

Active Publication Date: 2010-12-01
SHENZHEN NEPTUNUS PHARMA RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These have hindered the clinical application of targeted anticancer drugs

Method used

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  • Phenyl nitrone compounds containing stilbene sections and application thereof
  • Phenyl nitrone compounds containing stilbene sections and application thereof
  • Phenyl nitrone compounds containing stilbene sections and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1 according to route 1 synthetic formula (I) compound

[0052] 1.1 Synthesis of compound (2)

[0053] Add methyl bromomethylbenzoate 1 (5 g, 0.022 mol) and triethyl phosphite (5.4 g, 0.033 mol) into 50 mL of toluene, heat to 105 ° C and reflux for 24 hours, cool down to room temperature, and remove toluene by rotary evaporation , to obtain yellowish liquid 2 (5.8 g, 93%). 1 HNMR (400MHz, CDCl 3 )δ1.11-1.15(m, 6H), 3.03-3.05(m, 2H), 3.88(s, 3H), 4.07-4.10(m, 4H), 7.17(m, 2H), 7.85(m, 2H) ; MS(EI) m / z 166[M] + .

[0054] 1.2 Synthesis of compound (3)

[0055] Sodium methoxide (2.5g, 0.046mol) was dissolved in 50mL ether, compound 2 (5.8g, 0.035mol) and 3,5-dimethoxybenzaldehyde (2.5g, 0.015mol) were dissolved in 25mL ether and slowly Add dropwise into the sodium methoxide solution, add about 0.5 hours, stir at room temperature for 20 minutes, plate chromatography (TLC) monitor the reaction is complete, add 70mL dichloromethane, 100mL water, neutralize ...

Embodiment 2

[0062] Embodiment 2 screening compound by Caliper method

[0063] In this example, 12 compounds were screened against the in vitro kinases EGFR, HER2, PDGFRa, PDGFRb and SRC using the Caliper method, and the compound staurosporine was used as a standard control, and each compound was diluted to 10 concentration points for repeated well detection. The reaction conditions and results are shown in Table 1 and Table 2, respectively.

[0064] Table 1

[0065] Kinase

Enzyme concentration (nM)

ATP concentration (μM)

With or without MnCl 2

Reaction time

EGFR

8

2.3

Contains 10mM MnCl 2

1 hour

HER2

18

15

Contains 10mMMnCl 2

1 hour

PDGFRa

3.5

134

5 hours

PDGFRb

6

38

5 hours

SRC

1

36

1 hour

[0066] Table 2

[0067]

Embodiment 3

[0068] Embodiment 3 compound influences on cell proliferation activity

[0069] The effects of the above compounds 6-17 on the proliferation of HepG2, A549, BGC-823 and HCT116 cell lines were detected by MTT assay.

[0070]10 mM compounds were prepared in DMSO and diluted 1:5. Each compound was detected from a final concentration of 50 μM. 0.5 μl was pipetted from the corresponding compound plate and added to a cell culture plate, and incubated in a 37° C. incubator for 72 hours. Then the cell morphology was observed under an inverted microscope, and 20 μl of 5 mg / ml MTT solution prepared from sterile PBS was added to each well. Incubate in a 37°C incubator for 5 hours, add 100 μl triple dissolving solution, and dissolve overnight in a 37°C biochemical incubator. Absorbance values ​​were detected using Flexstation3. Record the IC50 value obtained from the analysis. Table 3 shows the inhibitory rates of the above-mentioned 12 compounds on cell line proliferation.

[0071] T...

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PUM

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Abstract

The invention discloses phenyl nitrone compounds containing stilbene sections and pharmaceutically acceptable salts thereof. The compounds can be used for treatment for cell hyperplasia of mammals, such as cancers, or be used as nerve protective agents. The invention also discloses a preparation method thereof, medicine composites containing the compounds and an application for preparing anti-tumour medicines.

Description

technical field [0001] The invention relates to phenylnitrone compounds containing stilbene fragments and pharmaceutically acceptable salts thereof. The compounds are used for treating mammalian cell hyperproliferative diseases, such as cancer, and can also be used as neuroprotective agents. The present invention also relates to the preparation method of the compound, the pharmaceutical composition containing these compounds and the application of these compounds in the preparation of antitumor drugs. technical background [0002] The treatment of tumors has always been a worldwide problem. With the increasing knowledge of tumor cell signal transduction pathways, the design of anti-tumor drugs targeting tumor-specific molecular targets has attracted more and more attention. Coupled with the development of crystal diffraction technology, combinatorial chemistry, molecular modeling, high-throughput screening technology and computer chemistry, targeted drugs are changing with e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C291/02A61K31/13A61K31/235A61K31/22A61K31/277A61K9/20A61P35/00A61P25/00
CPCC07C291/02A61K9/0019A61P25/00A61P35/00
Inventor 唐田陈学明王彦青马春铭李勇朱丹刘碧秀陈红黄传贵
Owner SHENZHEN NEPTUNUS PHARMA RES INST CO LTD
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