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Thienopyridine derivative, and preparation method and application thereof

A derivative, thiophene technology, applied in the field of medicine, can solve the problems of high mortality and poor prognosis of cancer patients, achieve the effect of inhibiting proliferation, increasing yield, and avoiding the operation of filtering and washing enaminone

Inactive Publication Date: 2011-04-27
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, in my country, cancer is the second cause of death after cardiovascular disease. Although some progress has been made in its treatment in recent years, with the application of a new generation of chemotherapy drugs such as gemcitabine and Gleevec, the survival of patients Gain some benefit, but most cancer patients still have poor prognosis and high mortality

Method used

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  • Thienopyridine derivative, and preparation method and application thereof
  • Thienopyridine derivative, and preparation method and application thereof
  • Thienopyridine derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Example 1 Preparation of 3-amino-6-(3-methoxyphenyl)thiophene[2,3-b]pyridine-2-carboxamide (4a)

[0011]

[0012] Heat m-methoxyacetophenone (5g, 33.3mmol) and N,N-dimethylformamide dimethyl acetal (DMFDMA) (9.2ml, 69.3mmol) to reflux until the reaction of the raw materials is complete, then cool the reaction in an ice bath liquid, the solid was separated out by suction filtration, the filter cake was washed with cold petroleum ether and cold ethanol, and dried to obtain 5.2 g of a yellow solid with a yield of 75%, which was directly used in the next reaction.

[0013] The above enaminone solid (1g, 4.9mmol), 2-cyanothioacetamide (0.74g, 7.35mmol), 1,4-diazabicyclo[2.2.2]octane (DABCO) (0.54 g, 2.45mmol) was dissolved in 8ml of absolute ethanol, heated to reflux until the reaction was complete, cooled the reaction solution to room temperature, adjusted the reaction system to neutrality with dilute hydrochloric acid, filtered the solid out by suction filtration, washe...

Embodiment 2

[0018] Example 2 Preparation of 3-amino-6-(3-fluorophenyl)thiophene[2,3-b]pyridine-2-carboxamide (4b)

[0019]

[0020] Heated m-fluoroacetophenone (5g, 36.2mmol) and N,N-dimethylformamide dimethyl acetal (DMF DMA) (10ml, 73.1mmol) to reflux until the reaction was complete, cooled the reaction solution in an ice bath, and pumped The solid was filtered out, and the filter cake was washed with cold petroleum ether and cold ethanol to obtain 4.8 g of a yellow solid with a yield of 69%, which was directly used in the next reaction.

[0021] The above-mentioned enaminone solid (1g, 5.2mmol), 2-cyanothioacetamide (0.8g, 7.7mmol), 1,4-diazabicyclo[2.2.2]octane (DABCO) (0.6 g, 2.6mmol) was dissolved in 8ml of absolute ethanol, heated to reflux until the reaction was complete, cooled the reaction solution to room temperature, adjusted the reaction system to neutrality with dilute hydrochloric acid, filtered the solid out by suction filtration, washed the filter cake with absolute et...

Embodiment 3

[0028] Example 3 Preparation of 3-amino-6-(3,4-dichlorophenyl)thiophene[2,3-b]pyridine-2-carboxamide (4c)

[0029]

[0030] 3,4-Dichloroacetophenone (5g, 26.5mmol) and N,N-dimethylformamide dimethyl acetal (DMFDMA) (8ml, 53.53mmol) were heated to reflux until the reaction was complete, and the reaction was cooled in an ice bath Liquid, the solid was separated out by suction filtration, the filter cake was washed with cold petroleum ether and cold ethanol, and dried to obtain 5.7 g of brown-red solid with a yield of 88%, which was directly used in the next reaction.

[0031] The above-mentioned enaminone solid (1g, 4.1mmol), 2-cyanothioacetamide (0.6g, 6.2mmol), 1,4-diazabicyclo[2.2.2]octane (DABCO) (0.5 g, 2mmol) was dissolved in 8ml of absolute ethanol, heated to reflux until the reaction was complete, cooled the reaction solution to room temperature, adjusted the reaction system to neutrality with dilute hydrochloric acid, filtered the solid out by suction filtration, was...

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Abstract

The invention discloses a thienopyridine derivative with a novel structure, a preparation method thereof and application thereof, and belongs to the field of medicaments. A pharmacological test proves that the thienopyridine derivative shown as a formula 4 has remarkable proliferation inhibition effect on human hepatoma cells HepG2 and the proliferation inhibition effect is achieved by inducing apoptosis; and a new anti-tumor medicament prepared from a 3-amino-thieno[2,3-b]pyridine-2-formamide derivative serving as a main active ingredient is a new choice for the treatment of tumors.

Description

technical field [0001] The invention belongs to the field of medicine, and specifically relates to a class of 3-amino-6-aryl-thieno[2,3-b]pyridine-2-carboxamide compounds with novel structures, a preparation method thereof and an antitumor drug use in compositions. Background technique [0002] Malignant tumors have become an important killer that endangers human health and survival. Especially in recent years, with the deterioration of the environment, the incidence of malignant tumors has shown an obvious upward trend. At present, in my country, cancer is the second cause of death after cardiovascular disease. Although some progress has been made in its treatment in recent years, with the application of a new generation of chemotherapy drugs such as gemcitabine and Gleevec, the survival of patients Some benefits have been obtained, but the prognosis of most cancer patients is still poor and the mortality rate is high. Therefore, it has become an urgent task to develop new...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D213/85C07D417/04A61K31/4365A61P35/00
Inventor 杨黎杨胜勇赵瀛兰余洛汀魏于全
Owner SICHUAN UNIV
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