Polyhaloacridones compound, intermediate and synthetic method thereof

A polyhalogenated acridone and compound technology, which is applied in the field of polyhalogenated acridone compounds, can solve the problems that the photoelectric properties of acridone derivatives have not been reported.

Inactive Publication Date: 2009-03-25
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the synthesis and photoelectric properties of polyhalogenated acridone derivatives on the benzene ring

Method used

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  • Polyhaloacridones compound, intermediate and synthetic method thereof
  • Polyhaloacridones compound, intermediate and synthetic method thereof
  • Polyhaloacridones compound, intermediate and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] 2,4,5-trichloro-6-phenylamino-1,3-phthalonitrile preparation (IV-A): 10.635 grams (0.04mol) chlorothalonil was added to a 250 ml three-necked bottle, and 150 Milliliter of N, N-dimethylformamide, 7.4 ml of aniline was slowly added under electromagnetic stirring, and the reaction was continued for 8 hours at room temperature. After the reaction was detected by TLC, the reaction solution was poured into 150 ml of water and stirred, and suction filtered to obtain The white solid was dried and recrystallized from acetone to obtain 10.1 g of white solid (yield 78.3%). Melting point: >250°C; MS (m / z, %): 322.0 (M + +H).

Embodiment 2

[0098] Preparation of 5-chloro-2,6-difluoro-6-phenylamino-1,3-phthalonitrile (IV-I): 10.8 grams (0.05mol) of 5-chloro-2,4,6-trifluoro -1,3-phthalonitrile was added to a 250 ml three-necked flask, 150 ml of N,N-dimethylformamide was added, and 10 grams of potassium carbonate was added, and 5 ml of aniline was slowly added under electromagnetic stirring, and at room temperature The reaction was continued for 3 hours. After the reaction was detected by TLC, the reaction solution was poured into 100 ml of water and stirred, and filtered with suction to obtain a white solid. After drying, it was recrystallized with acetone to obtain 13.3 g of a white solid (91.7% yield). Melting point: >250°C; MS (m / z, %): 290.0 (M + +H).

Embodiment 3

[0100] Preparation of 5-chloro-2,6-difluoro-6-p-chloroanilino-1,3-phthalonitrile (IV-J): 10.8 grams (0.05mol) of 5-chloro-2,4,6- Trifluoro-1,3-phthalonitrile was added to a 250 ml three-necked flask, 150 ml of N,N-dimethylformamide was added, 10 grams of potassium carbonate was added, and 4.2 grams of p-chloroaniline was added under electromagnetic stirring. The reaction was continued at room temperature for 18 hours. After the reaction was detected by TLC, the reaction solution was poured into 100 ml of water and stirred, filtered with suction to obtain a white solid. After drying, it was recrystallized with acetone to obtain 13.8 g of a white solid (yield 85.2%). Melting point: >250°C; MS (m / z, %): 324.0 (M + +H).

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Abstract

The invention discloses multi-halogenated acridone compounds, intermediates and a synthetic method thereof, wherein, the synthetic method comprises the steps: under the condition of alkali or no alkali, multi-halogenated m-phthalonitrile with the structural formula of (II) and phenylamine compound with the structural formula of (III) are reacted in a non-protonic solvent at certain temperature ( 0 to 90 DEG C ), thus generating the intermediate with the structural formula of (IV); then the intermediate (IV) is reacted with sulphuric acid to synthetize the multi-halogenated acridone compound with the structural formula of (V), and then the formula (V) is treated with alkylation or arylation reaction of nitrogen atoms to synthetize the multi-halogenated acridone compound (I).

Description

technical field [0001] The invention relates to polyhalogenated acridone compounds, intermediates and synthesis methods thereof. Background technique [0002] Many acridone compounds have good physiological activity and pharmacological activity (Chun, M.W.et al.Bioorg Med Chem Lett, 1997, 7 (7): 789-792; Itoigawa, M.et al.Cancer Lett, 2003,193 (2): 133-138; Kawa II, S. et al. Leukemia Res, 1999, 23(3): 263-269; Walser, A. et al. J. Med. Chem. 1991, 34, 1209-1221 ), such as 3,4-dihydro-2-(2H)-acridone has obvious killing effect on staphylococcus and yeast; 9-amino-3,4-di-hydrogen (2H)-acridone Derivatives have the physiological activity of enhancing memory; some acridone derivatives have low toxicity and high analgesic activity. More importantly, acridone compounds have anti-cancer (Antonini, I.et al.J.Med.Chem.1997,40,3749-3755; Taraporewala, I.B.et al.J.Med.Chem.1992,35 , 2744-2752), anti-HIV activity. Acridone compounds have attracted much attention. [0003] On the o...

Claims

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Application Information

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IPC IPC(8): C07D219/04C07D219/06
Inventor 严胜骄林军黄超李艳梅颜妤芸
Owner YUNNAN UNIV
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