Thienopyrrole derivative as well as preparation method and application thereof

A technology of pyrrole derivatives and thiophene, which is applied in the field of thienopyrrole derivatives and their preparation, can solve the problems of weak inhibition of colon cancer proliferation, unsatisfactory half-inhibition rate, and many impurities in the final product, and achieve inhibition of colon cancer proliferation, The preparation method is simple and feasible, and the effect of high purity

Inactive Publication Date: 2020-08-28
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The prior art shows that thienopyrrole derivatives have weak inhibition on the proliferation of colon cancer, especially the half-inhibition rate of colon cancer HCT116 and HT29 cells is not ideal; and in the preparation process, the control is not good, can not respond normally, and the product yield The yield is low, and the final product obtained has many impurities and low purity

Method used

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  • Thienopyrrole derivative as well as preparation method and application thereof
  • Thienopyrrole derivative as well as preparation method and application thereof
  • Thienopyrrole derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] A preparation method of thienopyrrole derivatives, which is prepared according to the following steps:

[0049] (1) Synthesis of 2-methyl azidocarboxylate:

[0050] Add sodium azide into the acetone / water solution of methyl chloroacetate under stirring at room temperature, then heat to 55-65°C for 4 hours, then place the reaction solution in a rotary evaporator, set the vacuum to -0.05--0.085MPa Rotary evaporation at a temperature of 45-55°C, the obtained residue was extracted with ethyl acetate, and then washed with an equal volume of saturated sodium bicarbonate solution and saturated saline solution respectively, after washing, anhydrous sodium sulfate was added to dry for 13 hours, filtered and dried After concentration, light yellow oily methyl 2-azidocarboxylate is obtained; the mol ratio of sodium azide to methyl chloroacetate is 2:1, and the mass volume ratio of sodium azide to methyl chloroacetate in acetone / water solution is 13: 200, the volume ratio of aceto...

Embodiment 2

[0063] A preparation method of thienopyrrole derivatives, which is prepared according to the following steps:

[0064] (1) Synthesis of 2-methyl azidocarboxylate:

[0065] Add sodium azide into the acetone / water solution of methyl chloroacetate under stirring at room temperature, then heat to 55~65°C for 3 hours, then put the reaction solution in a rotary evaporator, set the vacuum degree to -0.05MPa~-0.08 MPa, the temperature is 45 ℃ for rotary evaporation, the obtained residue is extracted with ethyl acetate, and then washed with an equal volume of saturated sodium bicarbonate solution and saturated saline solution respectively. After washing, anhydrous sodium sulfate is added to dry for 12 hours, and filtered Yellow oily 2-methyl azidocarboxylate; The mol ratio of sodium azide to methyl chloroacetate is 2:1, the mass volume ratio of sodium azide to the acetone / water solution of methyl chloroacetate is 13:200, acetone / The volume ratio of water is 2:1; the mass volume ratio...

Embodiment 3

[0078] A preparation method of thienopyrrole derivatives, which is prepared according to the following steps:

[0079] (1) Synthesis of 2-methyl azidocarboxylate:

[0080] Add sodium azide into the acetone / water solution of methyl chloroacetate under stirring at room temperature, then heat to 55-65°C for 5 hours, then place the reaction solution in a rotary evaporator, and set the vacuum degree to -0.05MPa~-0.08 MPa, the temperature is 55°C for rotary evaporation, the obtained residue is extracted with ethyl acetate, and then washed with an equal volume of saturated sodium bicarbonate solution and saturated saline solution respectively. After washing, anhydrous sodium sulfate is added to dry for 15 hours, and filtered Yellow oily 2-methyl azidocarboxylate; The mol ratio of sodium azide to methyl chloroacetate is 2:1, the mass volume ratio of sodium azide to the acetone / water solution of methyl chloroacetate is 13:200, acetone / The volume ratio of water is 2:1; the mass volume...

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Abstract

A thienopyrrole derivative is named as 3-phenyl-N-(3-(trifluoromethyl) phenyl)-4H-thieno[3,2-b]pyrrole-5-formamide, the molecular formula of the thienopyrrole derivative is C20H13F3N2OS, and the molecular weight of the thienopyrrole derivative is 386.4. The thienopyrrole derivative prepared by the inventor has the advantages of simple synthesis and strong stability, and can significantly inhibit the proliferation of colon cancer in vitro, IC50 values on colon cancer HCT116 and HT29 cells are 10.93 [mu] M and 6.25 [mu] M respectively, and can be developed as a lead drug for treating colon cancer. The preparation method is simple, feasible and high in yield, the yield of the final product can reach 68% or above, the prepared product is high in purity and few in impurity, the impurity contentis lower than 0.25%, the purity is high and can reach 99.0% or above, and a pharmaceutical common dosage form is prepared and is convenient to use.

Description

technical field [0001] The invention relates to the field of chemical industry and pharmaceuticals, in particular to a thienopyrrole derivative and its preparation method and application. Background technique [0002] Colorectal cancer is one of the most common malignant tumors of the digestive tract, and its incidence and mortality rank among the top four among cancers. Comprehensive treatment such as surgery, radiotherapy and chemotherapy is commonly used in the treatment of colorectal cancer, but its treatment effect is not good, seriously affecting the quality of life and life expectancy of patients. Therefore, the development of new targeted therapeutic strategies is of great significance for the treatment of colorectal cancer. [0003] In recent years, tumor chemotherapy has made considerable progress, and the survival time of cancer patients has been significantly prolonged. In particular, breakthroughs have been made in the treatment of leukemia and malignant lympho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61K31/407A61P35/00A61P1/00
CPCA61P1/14A61P35/00C07D495/04
Inventor 胡春生方波丁勇秦红霞罗亚飞徐志刚孟江平陈中祝
Owner CHONGQING UNIV OF ARTS & SCI
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