N-benzyl-acridone, derivatives of N-benzyl-acridone and preparation methods and application of N-benzyl-acridone and derivatives

A group and reaction technology, applied in the field of N-benzyl-acridone and its derivatives, can solve problems such as hindering the movement of replicators

Active Publication Date: 2011-08-10
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] During the DNA replication process, a high degree of helicalization of DNA occurs at the front of the replicator, which hinders the replicator from moving along the DNA chain; the same problem also exists in the process of DNA transcription

Method used

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  • N-benzyl-acridone, derivatives of N-benzyl-acridone and preparation methods and application of N-benzyl-acridone and derivatives
  • N-benzyl-acridone, derivatives of N-benzyl-acridone and preparation methods and application of N-benzyl-acridone and derivatives
  • N-benzyl-acridone, derivatives of N-benzyl-acridone and preparation methods and application of N-benzyl-acridone and derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] The preparation of embodiment 1,2-nitro-acridone

[0067] Acridone (1.17g, 6mM) (purchased in Guangzhou Qihua Medical Equipment Co., Ltd., No. A0133), adding 6 ml of acetic acid with a mass concentration of 36%, stirred at room temperature, added 12 ml of glacial acetic acid, 6 ml of concentrated nitric acid (mass The concentration is 65%), keep the temperature at 50-60°C for 4 hours, cool to room temperature, add ice water, precipitate a yellow solid, filter with suction, wash with ice water, recrystallize with ethanol to obtain 1.38 g of product, and directly proceed to the next step reaction , yield 96%.

Embodiment 2

[0068] The preparation of embodiment 2,9-(3,5-dimethoxybenzyl)-2-nitroacridone

[0069] Under the protection of argon, in a three-necked round-bottomed flask equipped with 15 mL of dry DMF, add 720 mg (3 mmol) of 2-nitro-acridone compound, 160 mg (4.0 mmol) of sodium hydride, stir at room temperature for 1 h, and then add 6 mmol of 3, 5-Dimethoxybenzyl chloride, 99mg (0.6mmol) potassium iodide, stirred overnight, added water, stirred rapidly under ice-water bath, yellow crystals precipitated, filtered to obtain a yellow solid, recrystallized with chloroform to obtain 790mg yellow crystals, filtrate After spin-drying and analyzing by column chromatography, 99 mg of the product was obtained, and the yield was 76%. m.p.242-244°C.

[0070] The structural confirmation data are as follows:

[0071] 1 H NMR (300MHz, DMSO-d6) δ: 3.67 (s, 6H), 5.79 (s, 2H), 6.33 (brs, 2H), 6.44 (brs, 1H), 7.47 (m, 1H), 7.70 (m, 1H), 7.79-7.88(m, 2H), 8.38(m, 1H), 8.50(m, 1H), 9.07(m, 1H).

Embodiment 3

[0072] The preparation of embodiment 3,9-(3,5-dimethoxybenzyl)-2-aminoacridone

[0073] Under argon protection, in a 50ml three-necked round-bottomed flask, add 780mg (2mmol) 9-(3,5-dimethoxybenzyl)-2-nitroacridone compound, 10ml ethanol, 5ml 30% sulfurized Sodium aqueous solution, stirred overnight at about 100°C, added water, stirred rapidly under an ice-water bath, yellow crystals precipitated, filtered to obtain 670 mg of yellow crystals by recrystallization from ethanol as a yellow solid, with a yield of 93%. m.p.290-291°C.

[0074] The structural confirmation data are as follows:

[0075] 1 H NMR (300MHz, DMSO-d6) δ: 3.66(s, 6H), 5.31(s, 2H), 5.65(s, 2H), 6.27(m, 2H), 6.42(m, 1H), 7.14(m, 1H), 7.25(m, 1H), 7.43(m, 1H), 7.53~7.55(m, 2H), 7.67(m, 1H), 8.34(m, 1H);

[0076] 13 C NMR (75MHz, DMSO-d6) δ: 49.4, 55.6, 98.7, 104.6, 107.7, 116.2, 117.6, 120.9, 121.0, 123.5, 123.9, 127.2, 134.0, 134.5, 139.8, 141.9, 144.3, 161.4, 176.6.

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Abstract

The invention discloses N-benzyl-acridone, derivatives of the N-benzyl-acridone and preparation methods and application of the N-benzyl-acridone and the derivatives. A structural formula of a compound is shown as a formula (I), wherein R1, R2, R3, R4 and R5 are all randomly selected from the following substituent groups: H, OH, NH2, Cl, F, Br, I, CN, NO2, CH3, OCH2Ph and O(CH2)nCH3; n in O(CH2)nCH3 is an integer in the range of 0 to 3; Z is randomly selected from the following substituent groups: CH2 and SO2; A is randomly selected form the following substituent groups: S, O and NH; R6, R7, R8, R9, R10, R11, R12 and R13 are all randomly selected from the following substituent groups: H, OH, NH2, Cl, F, Br, I, CN, NO2, CH3 and the following a and b; necessarily, only one substituent group of the R6, the R7, the R8, the R9, the R10, the R11, the R12 and the R13 is a or b; a represents NHCO(CH2)nR or CONH(CH2)nR, wherein n is an integer in the range of 0 to 3 and R represents tertiary amine; and b represents NHCOBNH2 or CONHBNH2, wherein B is an alkyl connection chain or an alkyl connection chain substituted heteroatom. A cell proliferation inhibition test result shows that the compound in the formula I can better inhibit cancer cell CCRF-CEM from growing, wherein part of compounds show higher activities than a parent compound (10-(3,5-dimethoxyphenyl) acridone). (the formula I).

Description

technical field [0001] The present invention relates to N-benzyl-acridone and its derivatives as well as their preparation method and application. Background technique [0002] Malignant tumor is a common and frequently-occurring disease that seriously threatens human life and health. The mortality rate of human beings caused by malignant tumors is the first among all diseases. Therefore, the research on its prevention and treatment has always been valued by countries all over the world. [0003] During the DNA replication process, a high degree of helicalization of DNA occurs at the front of the replicator, which hinders the replicator from moving along the DNA chain; the same problem also exists in the process of DNA transcription. DNA topoisomerases are a class of enzymes that exist in the nucleus. They can catalyze the breaking and joining of DNA strands, thereby controlling the topological state of DNA. In this process, in order to maintain the integrity of DNA, the t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/08C07D401/12C07D413/12A61K31/473A61K31/5377A61P35/00
CPCY02P20/55
Inventor 蒋宇扬高春梅刘峰栾旭东谭春燕刘红霞
Owner SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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