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Aza-acridine aromatic ring derivative as well as preparation method and application thereof

A technology of azaacridine and aromatic ring, which is applied in the field of azaacridine aromatic ring derivatives and its preparation, can solve the problems of toxic side effects and high treatment cost, and achieve low cytotoxicity, low cytotoxicity and important economic value Effect

Inactive Publication Date: 2015-01-21
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Tumor chemotherapy drugs have toxic and side effects on normal cells of the body, and the treatment cost is high

Method used

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  • Aza-acridine aromatic ring derivative as well as preparation method and application thereof
  • Aza-acridine aromatic ring derivative as well as preparation method and application thereof
  • Aza-acridine aromatic ring derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Synthesis of Azaacridine Aromatic Ring Derivative T1

[0037] 1) Synthesis of intermediate compound 1:

[0038] 3.5 mL of 4-benzylpiperidone and 20 mL of phosphorus oxychloride (POCl 3 ) was added to a 100mL round-bottomed flask, and after stirring for 10min, the anthranilic Add 3 g to the above reaction solution, stir and reflux for 2 hours; stop heating, cool to room temperature, slowly pour the reaction solution into a beaker filled with crushed ice, let stand for 3 to 5 minutes, stir, and slowly drop into the beaker Add ammonia water, adjust the pH to 8-9, a large amount of yellow precipitates are formed, stop dripping ammonia water, filter with suction, and obtain yellow precipitates; use petroleum ether: acetone = 12:1 system to separate through the column, and use acetone to recrystallize to obtain light Yellow crystal intermediate compound 1;

[0039] Compound 1, 1H NMR (400MHz, CDCl 3 )δ8.11(d, J=8.4Hz, 1H), 7.98(d, J=8.4Hz, 1H), 7.65(t, J=7.7Hz, ...

Embodiment 2

[0063] Example 2 Synthesis of Azaacridine Aromatic Ring Derivative T3

[0064] 1) Synthesis of intermediate compound 1:

[0065] 3.5 mL of 4-benzylpiperidone and 20 mL of phosphorus oxychloride (POCl 3 ) into a 100mL round bottom flask, stirred for 10min, then added 3g of anthranilic acid into the above reaction solution, stirred and refluxed for 2h; stopped heating, cooled to room temperature, slowly poured the reaction solution into a container filled with crushed ice In the beaker, let it stand for 3-5 minutes and then stir, slowly add ammonia water to the beaker, adjust the pH to 8-9, a large amount of yellow precipitate is formed, stop dripping ammonia water, filter with suction, and get a yellow precipitate; use petroleum ether : The system of acetone=12:1 is separated by column, and recrystallized with acetone to obtain light yellow crystal intermediate compound 1;

[0066] Compound 1, 1H NMR (400MHz, CDCl 3 )δ8.11(d, J=8.4Hz, 1H), 7.98(d, J=8.4Hz, 1H), 7.65(t, J=7.7...

Embodiment 3

[0090] Example 3 Synthesis of Azaacridine Aromatic Ring Derivative T11

[0091] 1) Synthesis of intermediate compound 1:

[0092] 3.5 mL of 4-benzylpiperidone and 20 mL of phosphorus oxychloride (POCl 3 ) into a 100mL round bottom flask, stirred for 10min, then added 3g of anthranilic acid into the above reaction solution, stirred and refluxed for 2h; stopped heating, cooled to room temperature, slowly poured the reaction solution into a container filled with crushed ice In the beaker, let it stand for 3-5 minutes and then stir, slowly add ammonia water to the beaker, adjust the pH to 8-9, a large amount of yellow precipitate is formed, stop dripping ammonia water, filter with suction, and get a yellow precipitate; use petroleum ether : The system of acetone=12:1 is separated by column, and recrystallized with acetone to obtain light yellow crystal intermediate compound 1;

[0093] Compound 1, 1H NMR (400MHz, CDCl 3 )δ8.11(d, J=8.4Hz, 1H), 7.98(d, J=8.4Hz, 1H), 7.65(t, J=7....

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PUM

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Abstract

The invention discloses an aza-acridine aromatic ring derivative as well as a preparation method and application thereof, belonging to the technical field of medicaments. A structural formula of the aza-acridine aromatic ring derivative is as shown by a formula I, wherein m is 0 or 1, n is 1 or 2, and R is one of H, CH3 and NO2. The obtained aza-acridine aromatic ring derivative disclosed by the invention has synergistic activities in tumor chemotherapeutic medicaments, and is small in cytotoxic effect. Because the aza-acridine aromatic ring derivative is low in cytotoxic effect and generally has synergistic effects on the tumor chemotherapeutic medicaments, the aza-acridine aromatic ring derivative is of a novel synergist of the chemotherapeutic medicaments, has an important improvement effect on tumor chemotherapy, and also has important economic values.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to an azaacridine aromatic ring derivative and a preparation method and application thereof. Background technique [0002] Tumor chemotherapy drugs have toxic and side effects on normal cells of the body, and the treatment costs are high. Reducing the amount of chemotherapeutic drugs can reduce the cost of treatment and potentially reduce their toxic side effects on normal cells. Acridine is a common mother nucleus of chemically synthesized drugs, and its derivatives have different pharmacological effects due to their different structures. Synthesizing and screening out low-toxic new synthetic drugs with synergistic activity of tumor chemotherapy drugs will have an important role in improving cancer chemotherapy, and also have important economic value, providing a new solution for the attenuation and efficiency enhancement of tumor chemotherapy. Contents of the inve...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/4745A61P35/00
CPCC07D471/04
Inventor 杨联河岑娟辛凯王建红赵雪艳赵会君
Owner HENAN UNIV OF CHINESE MEDICINE
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