Synthesis method for TB derivatives with human liver cancer HepG2 cell resisting activity

A synthesis method and cell activity technology, applied in the fields of drug combination, organic chemistry, anti-tumor drugs, etc., can solve the problems of easy clinical metastasis and recurrence, poor overall effect, and insignificant early symptoms of liver cancer, and achieve high practical application value, The effect of short reaction time and high yield

Active Publication Date: 2015-09-09
GUANGDONG CELL BIOTECHNOLOGY CO LTD
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Problems solved by technology

The effective way to cure early liver cancer is surgical therapy. However, because the early symptoms of liver cancer are not obvious, most patients are already at an advanced stage when they see a doctor. Although surgical resection is reluctantly performed, the overall effect is poor because of clinical metastasis and recurrence.

Method used

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  • Synthesis method for TB derivatives with human liver cancer HepG2 cell resisting activity
  • Synthesis method for TB derivatives with human liver cancer HepG2 cell resisting activity
  • Synthesis method for TB derivatives with human liver cancer HepG2 cell resisting activity

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preparation example Construction

[0036] The synthesis method of the TB derivatives comprises: TB-chalcone compounds, TB-flavonoids and TB-benzimidazole compounds, and the anti-human liver cancer HepG2 cell activity of the TB derivatives is determined by the MTT method;

[0037] 1, the synthetic method of TB-chalcones compound:

[0038]

[0039] 1) Synthesis of compound 4:

[0040] Add 0.5mmol of compound 1, namely 2,8-diformyl TB, and 0.75mmol of substituted-2-hydroxyacetophenone into the round bottom flask, and the substituted-2-hydroxyacetophenone is 4-OCH 3 -2-Hydroxyacetophenone; 5-CH 3- 2-Hydroxyacetophenone or 5-OCH 3 -2-Hydroxyacetophenone, 1.8mmol NaOH and 5mL absolute ethanol, reacted at 60°C, tracked by TLC, the solution turned orange; after the reaction was completed, cooled to room temperature, added ice water, and adjusted the pH to 3-4; Suction filtration, washing with water, purification of the filter cake by column chromatography, petroleum ether: ethyl acetate = 2:1, to obtain orange po...

Embodiment 1

[0072] Embodiment 1: Take the synthesis of the target product 4a as an example.

[0073] The synthesis steps include: 1) using 4-bromoaniline as the starting material to react with paraformaldehyde at low temperature to obtain the compound 2,8-dibromo-TB; 2) using 2,8-dibromo-TB as the raw material Compound 1 was obtained by formylation and Suzuki C-C coupling; 3) Compound 1 was subjected to aldol condensation reaction with 2-hydroxy-5-methylbenzophenone to obtain the target compound 4a, a total of three steps. 1) 4-bromoaniline reacts with paraformaldehyde at -15°C to generate compound 2,8-dibromo-TB, and its reaction formula is as follows:

[0074]

[0075] At -15°C, add 60mmol p-bromoaniline and 120mmol paraformaldehyde into a 250mL dry three-necked round-bottom flask, stir, and slowly drop 120mL trifluoroacetic acid into it with a constant pressure funnel to form a maroon solution. After the dropwise addition, Stirring was continued for 6 days at 0°C. After the reacti...

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Abstract

The invention discloses a synthesis method for TB derivatives with human liver cancer HepG2 cell resisting activity, belonging to a synthesis method for TB derivatives. The synthesis method comprises the steps of carrying out aldol condensation reaction on different formyl-substituted TB derivatives and o-acetylphenol compounds to obtain TB-chalcone compounds; and carrying out condensation reaction on different formyl-substituted TB derivatives and diaminobenzene under the catalysis of silicon sulfoacid (SSA) to obtain TB-benzimidazole compounds, and controlling different reaction conditions by taking the TB-chalcone compounds as raw materials to obtain a series of TB-flavonoid compounds. The activities of two different types of TB derivatives resisting a human liver cancer HepG2 cell are primarily researched, and six products with favorable human liver cancer HepG2 cell resisting activity is screened, so that the basis is laid for developing the TB derivatives into novel anti-cancer drugs. The synthesis method has the advantages of relatively high reaction yield, mild reaction condition, simplicity in operation, very short reaction time, high yield, simplicity and convenience in aftertreatment, environment-friendly reaction, high economic efficiency, high efficiency and extremely high actual application value.

Description

technical field [0001] The invention relates to a method for synthesizing TB derivatives, in particular to a method for synthesizing TB derivatives with anti-human liver cancer HepG2 cell activity. Background technique [0002] Due to environmental pollution and bad living habits, malignant tumors have become the number one killer of human health, and liver cancer is one of the most common malignant tumors. Currently, cancer treatment methods include surgery, radiation therapy, and drug therapy. The effective way to cure early liver cancer is surgical therapy. However, because the early symptoms of liver cancer are not obvious, most patients are already at an advanced stage when they see a doctor. Although surgical resection is reluctantly performed, the overall effect is poor because of clinical metastasis and recurrence. In recent years, people have been continuously developing new drugs to fight against this disease. As an important means of treating liver cancer, drugs ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/08A61P35/00
CPCC07D487/08
Inventor 王园江宛瑜黄树颖吴翚
Owner GUANGDONG CELL BIOTECHNOLOGY CO LTD
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