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Anti-tumor compound aiming at Fyn-CD147 signal pathway target point, and preparation method and application of anti-tumor compound

A signaling pathway and anti-tumor drug technology, which is applied in the preparation of carbon-based compounds, organic compounds, anti-tumor drugs, etc., can solve the problems of high prices and few anti-tumor drugs

Active Publication Date: 2020-04-07
XIANGYA HOSPITAL CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, anti-tumor drugs are still few and expensive, and further exploration of other anti-tumor compounds is needed

Method used

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  • Anti-tumor compound aiming at Fyn-CD147 signal pathway target point, and preparation method and application of anti-tumor compound
  • Anti-tumor compound aiming at Fyn-CD147 signal pathway target point, and preparation method and application of anti-tumor compound
  • Anti-tumor compound aiming at Fyn-CD147 signal pathway target point, and preparation method and application of anti-tumor compound

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preparation example Construction

[0031] The preparation method of the above-mentioned antitumor compound according to an embodiment of the present invention comprises the following steps: mixing 4-methoxy-3-hydroxyacetophenone, 4-biphenylformaldehyde and alkali solution, stirring at room temperature for 24 to 30 hours, Concentrate and dry to obtain the above antitumor compound.

[0032] In a specific example, the molar ratio of 4-methoxy-3-hydroxyacetophenone to 4-biphenylformaldehyde is (0.8-1.2):1.

[0033] In a specific example, the alkaline solution is an aqueous sodium hydroxide solution, wherein the ratio of the mass of sodium hydroxide to the volume of water is (16-18) mg:1 mL.

[0034] In a specific example, the temperature of the alkaline solution is 0° C. to 10° C., and using a low-temperature alkaline solution for preparation can prevent excessive exothermic heat during the reaction.

[0035] In a specific example, the following step is further included: recrystallizing the antitumor compound with...

Embodiment 1

[0046] Add sodium hydroxide aqueous solution (NaOH 290mg / H2 O 15mL) and water (2mL), cooled to below 10°C with an ice-water bath, added 4-methoxy-3-hydroxyacetophenone (997mg, 6mmol) and stirred for 30 minutes, then added 4-biphenylcarbaldehyde (1.09g , 6 mmol) was stirred for 1 hour. Then rise to room temperature and stir for 26 hours, concentrate the reaction solution, add 200 mL of ethyl acetate, wash with 3N hydrochloric acid and water successively, then dry with anhydrous magnesium sulfate, filter and concentrate and recrystallize with ethanol to obtain the target product 1.4 as a yellow solid. g, based on dividing the actual yield by the theoretical yield to obtain a yield of 71%. The NMR spectrum information is: 1 H NMR (400MHz, CDCl 3 )δ7.85(d, J=15.6Hz, 1H), 7.72(d, J=8.3Hz, 2H), 7.69–7.61(m, 6H), 7.57(d, J=15.6Hz, 1H), 7.47( t, J=7.5Hz, 2H), 7.38(t, J=7.3Hz, 1H), 6.95(d, J=9.0Hz, 1H), 3.99(s, 3H); 13 C NMR (125MHz, DMSO) δ187.9, 152.8, 147.1, 142.8, 142.3, 139.7,...

Embodiment 2

[0048] Add sodium hydroxide aqueous solution (NaOH 190mg / H 2 O 15mL) and water (2mL), cooled to below 10°C with an ice-water bath, added 4-methoxy-3-hydroxyacetophenone (997mg, 6mmol) and stirred for 30 minutes, then added 4-biphenylcarbaldehyde (1.09g , 6 mmol) was stirred for 1 hour. Then rise to room temperature and stir for 20 hours, concentrate the reaction solution, add 200 mL of ethyl acetate, wash with 3N hydrochloric acid and water successively, then dry with anhydrous magnesium sulfate, filter and concentrate and recrystallize with ethanol to obtain the target product 1.1 as a yellow solid g.

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Abstract

The invention relates to an anti-tumor compound aiming at a Fyn-CD147 signal pathway target point, and a preparation method and an application of the anti-tumor compound. The anti-tumor compound has astructure represented by the following structural formula I which is described in the specification. The anti-tumor compound disclosed by the invention is generated by carrying out a reaction of 4-methoxy-3-hydroxyacetophenone and 4-biphenylformaldehyde in an alkaline solution at room temperature. The anti-tumor compound can effectively inhibit proliferation of skin tumor cells, colon cancer cells, liver cancer cells and lung cancer cells; the half-inhibition concentration of the anti-tumor compound on human skin malignant melanoma cells SK-Mel-28 is 3.6 [mu]M, and it is indicated that the anti-tumor compound has strong ability of inhibiting tumor growth and proliferation and inducing tumor cell apoptosis, and can be applied to preparation of anti-tumor drugs.

Description

technical field [0001] The invention relates to the field of medicines, in particular to an anti-tumor compound aimed at the target of the Fyn-CD147 signaling pathway and its preparation method and application. Background technique [0002] Tumor is a kind of cell proliferative disease, and tumor cells have three remarkable basic characteristics: immortality, migration and loss of contact inhibition. At the cellular level, the occurrence of cancer is an extremely accidental event. Genetically, cancer develops from one cell, from a cell that has lost its proliferation control. There are trillions of cells in the human body, and billions of cells divide every day. In theory, almost any cell may become cancerous due to the change of genetic composition, but it is not the case in practice. The malignant transformation of cells requires multiple genetic changes, that is, multiple genetic mutations in a cell. Tumor initiation is thus a gradual process involving multistage react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/74A61K31/12A61P35/00
CPCC07C49/84C07C45/74A61K31/12A61P35/00
Inventor 陈翔彭聪龙菁粟娟赵爽李雅芸李可可张旭
Owner XIANGYA HOSPITAL CENT SOUTH UNIV
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