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N-benzyl-9, 10- dihydro-acridine compound and preparation method thereof

A benzylacridone and compound technology, applied in the field of N-benzyl-9, can solve the problems of cumbersome reaction steps and harsh reaction conditions, and achieve the effect of simple operation and high yield

Inactive Publication Date: 2009-10-14
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

The synthesis of 9,10-dihydroacridine is currently mostly obtained by reducing the corresponding acridone with sodium / amyl alcohol or lithium aluminum hydride, but metal sodium and lithium aluminum hydride are particularly active and decompose rapidly when they meet water, so they must be in the absence of Operate under water anaerobic conditions, the reaction conditions are harsh; or use acridine as raw material, sequentially use boron trifluoride, sodium cyanoborohydride (Sodiumcyanoborohydride), etc. to prepare, the reaction steps are cumbersome

Method used

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  • N-benzyl-9, 10- dihydro-acridine compound and preparation method thereof
  • N-benzyl-9, 10- dihydro-acridine compound and preparation method thereof
  • N-benzyl-9, 10- dihydro-acridine compound and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0031] 1) Synthesis of N-benzylacridone

[0032] Under the protection of argon, in a three-necked round-bottomed flask containing 15 mL of dry N,N-dimethylformamide (DMF), add 585 mg (3 mmol) of acridone (purchased from Guangzhou Qihua Medical Equipment Co., Ltd., No. A0133), 160mg (4.0mmol) sodium hydride, stirred at room temperature for 1h, then added 6mmol benzyl chloride, 990mg (6mmol) potassium iodide, stirred overnight, added 30ml water, stirred rapidly under ice-water bath, yellow crystals were precipitated, filtered to obtain yellow Crystal: recrystallized with ethanol to obtain 770 mg of light yellow crystal N-benzylacridone with a yield of 90% and a melting point of 180-181° C. (determined by X-4 micro melting point apparatus). The characterization data of N-benzylacridone are as follows: 1 H NMR (300MHz, CDCl 3 ): δ5.61 (s, 2H), 7.20-7.37 (m, 9H), 7.62 (m, 2H), 8.60 (m, 2H).

[0033] 2) Synthesis of N-benzyl-9,10-dihydroacridine

[0034] Add N-benzylacridone (1m...

Embodiment 2

[0036] 1) Synthesis of N-(3,5-dimethoxy)benzylacridone

[0037] Under the protection of argon, in a three-necked round-bottomed flask containing 15 mL of dry N,N-dimethylformamide (DMF), add 585 mg (3 mmol) of acridone (purchased from Guangzhou Qihua Medical Equipment Co., Ltd., No. A0133), 160mg (4.0mmol) sodium hydride, stirred at room temperature for 1h, then added 6mmol 3,5-dimethoxyl-benzyl chloride (prepared according to the method in Gao Chunmei's 2007 doctoral dissertation of Guangzhou Institute of Chemistry, Chinese Academy of Sciences), 990mg ( 6mmol) potassium iodide, stirred overnight, added 30ml of water, stirred rapidly under an ice-water bath, yellow crystals were precipitated, filtered to obtain yellow crystals; recrystallized with ethanol to obtain yellow crystals, namely N-(3,5-dimethoxy) Benzylacridone 940mg, yield 91%, melting point: 229-230°C (determined by X-4 micro melting point apparatus). The characterization data of N-(3,5-dimethoxy)benzylacridone ar...

Embodiment 3

[0041] 1) Synthesis of N-(3,5-dibenzyloxy)benzylacridone

[0042] Under the protection of argon, in a three-necked round-bottomed flask containing 15 mL of dry N,N-dimethylformamide (DMF), add 585 mg (3 mmol) of acridone (purchased from Guangzhou Qihua Medical Equipment Co., Ltd., No. A0133), 160mg (4.0mmol) sodium hydride, stirred at room temperature for 1h, then added 6mmol3,5-dibenzyloxy-benzyl chloride (prepared according to the method in Gao Chunmei's doctoral dissertation of Guangzhou Institute of Chemistry, Chinese Academy of Sciences in 2007), 990mg (6mmol ) Potassium iodide, stirred overnight, added water, stirred rapidly under ice-water bath, yellow crystals were precipitated, filtered to obtain yellow crystals; recrystallized with ethanol to obtain light yellow crystals, namely N-(3,5-dibenzyloxy)benzyl Acridone 1.3g, yield 87%, melting point: 170-171°C. The characterization data of N-(3,5-dibenzyloxy)benzylacridone are as follows: 1 H NMR (500MHz, CDCl3): δ4.93(s...

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Abstract

The invention discloses an N-benzyl-9, 10-dihydro-acridine compound and a preparation method thereof. A structure of the N-benzyl-9, 10-dihydro-acridine compound is shown as a formula I, wherein the R1 is H, OCH2Ph or OCH3; the R2 is H or OCH3; the R3 is H, OCH2Ph or OCH3. The method for preparing the N-benzyl-9, 10-dihydro-acridine compound comprises the steps: under the oxygen isolating condition, adding sodium borohydride and an N-benzyl acridone compound into organic solvent (A) to react for 4-24h at 50-100 DEG C; and then, adding solvent (B) to continuously react for 0.5-1h at 50 -100 DEG C and obtaining the compound shown as the formula I, wherein the organic solvent (A) is diethylene glycol dimethyl ether or tetrahydrofuran, and solvent (B) is methanol or water. The compound has the outstanding advantages of cheap and available materials, simple and convenient synthetic method, higher yield, and the like.

Description

technical field [0001] The invention relates to N-benzyl-9,10-dihydroacridine compounds and a preparation method thereof. Background technique [0002] Acridine compounds are widely used in medicine, dyes and photosensitive materials, so they have attracted people's attention in terms of synthesis methods and application research. Most of the acridine compounds are colored and were used as pigments and dyes when they were first discovered. At the beginning of the 20th century, some acridine compounds were found to have antiseptic and antibacterial effects, and were used as antibacterial and antimalarial drugs during the First World War. The anticancer drug amsacrine (AMSA) has been widely used at home and abroad as a second-line treatment drug for acute leukemia. [0003] 9,10-dihydroacridines are a class of more important acridine compounds, they have good antioxidant properties and play an important role in the fields of organic synthesis and medicinal chemistry, so the ...

Claims

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Application Information

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IPC IPC(8): C07D219/02
Inventor 蒋宇扬高春梅
Owner SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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