Benzofuroxan derivative and preparation method and application thereof

A technology of benzofurazan and derivatives, applied in the field of medicine, can solve the problems of poor long-term curative effect, high toxicity and the like

Inactive Publication Date: 2015-09-02
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the commonly used anti-tumor drugs in clinic mainly include alkylating agents, antimetabolite drugs, anti-tumor an...

Method used

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  • Benzofuroxan derivative and preparation method and application thereof
  • Benzofuroxan derivative and preparation method and application thereof
  • Benzofuroxan derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Example 1: Preparation of class A benzofurazan derivatives 4-amino-7-nitrobenzofurazan

[0080] (1) Preparation of intermediate 2, 6-dichloronitrosobenzene

[0081] In a 100 ml reaction flask, add 2,6-dichloroaniline (1.62 g, 10 mmol), 35 ml of glacial acetic acid and 30% hydrogen peroxide (8.0 ml, 70 mmol), mix well, and react at 35°C for 48 h. After suction filtration and natural drying, 2, 6-dichloronitrosobenzene (1.49 g) was obtained as an off-white flaky solid with a yield of 85.0% and a melting point of 174-175°C.

[0082] (2) Preparation of intermediate 4-chlorobenzofurazan

[0083] In a 100 ml reaction flask, add 2, 6-dichloronitrosobenzene (1.44 g, 8.2 mmol), sodium azide (0.70 g, 11 mmol) and 25 ml of dimethyl sulfoxide, and heat to 100°C , after the bubbling stopped, the temperature was raised to 120°C, and the reaction was continued for 0.5 h. 50 ml of water was added to the reaction system, and a large amount of solid was precipitated. Suction filtrati...

Embodiment 2

[0089] Example 2: Preparation of Class B benzofurazan derivatives 5-amino-6-nitro-1-oxybenzofurazan

[0090] (1) Preparation of intermediate 1, 5-dichloro-2, 4-dinitrobenzene

[0091] In a 100 ml reaction flask, add 15 ml of fuming nitric acid, lower to 0°C, slowly add 2,4-dichloronitrobenzene (4.60 g, 24.3 mmol) dropwise, after the drop is completed, heat up to 50°C, and react for 12 h . The reaction solution was slowly poured into an appropriate amount of crushed ice in batches, and a pale yellow solid was precipitated, which was filtered by suction. The filter cake was washed with water and air-dried to obtain light yellow powder 1, 5-dichloro-2, 4-dinitrobenzene (5.45 g), yield 94.6%, melting point: 100~101°C.

[0092] (2) Preparation of intermediate 1-chloro-5-(4-benzylamino)-2, 4-dinitrobenzene

[0093] In a 50 ml reaction bottle, add 1, 5-dichloro-2, 4-dinitrobenzene (0.59 g, 2.5 mmol), 10 ml absolute ethanol, benzylamine (0.27 g, 2.5 mmol) and triethylamine (0.4 ml...

Embodiment 3

[0099] Example 3: Preparation of Class C Benzofurazan Derivatives 5-Amino-6-Nitrobenzofurazan

[0100] (1) Preparation of 5-(4-benzylamino)-6-nitrobenzofurazan (C 1 )

[0101] Dissolve 5-(4-benzylamino)-6-nitro-1-benzofurazan oxide in an appropriate amount of toluene, add triphenylphosphine, and react at 80°C for 3 hours to generate 5-(4-benzylamino)- 6-Nitrobenzofurazan C 1 (48 mg), yield 29.2%, melting point: 94~95℃. (Spectral data see Table 1 in C 1 )

[0102] Compound C in Table 1 2 The R group is 4-phenylpiperazinyl, and the method is the same as above.

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Abstract

The invention relates to the field of a medical technology and discloses a Benzofuroxan derivative and a preparation method and an application thereof. According to the invention, 1,4,5,6,7 sites of a Benzofuroxan structure are subjected to derivatization to obtain the Benzofuroxan derivative. The general molecular formula of the Benzofuroxan derivative is as shown in the specification. The compound provided by the invention has an obvious inhibiting effect on tumor cells and can be used in the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to benzofurazan derivatives and their preparation methods and uses. Background technique [0002] Malignant tumors seriously threaten human health. Clinical tumor treatment methods include surgery, chemical drug therapy, and radiotherapy. Among them, chemotherapy has become an important means of tumor treatment. At present, the commonly used anti-tumor drugs mainly include alkylating agents, antimetabolites, anti-tumor antibiotics, anti-tumor herbal medicines, hormones, etc., but they have the disadvantages of high toxicity and poor long-term efficacy. Therefore, research and development of anti-tumor compounds with new structural types has important theoretical significance. [0003] The structure of nitrogen-containing heterocyclic compounds is similar to that of purine, pyrimidine and other bases, and has good compatibility with the biological environment, and has broad appli...

Claims

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Application Information

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IPC IPC(8): C07D271/12C07D413/04A61P35/00
CPCC07D271/12C07D413/04
Inventor 孟庆国杜广营谭文娟杨帆柴晓云刘兴东朱伟伟白国静徐阳荣王文智杨静静李新利蔡艺张晰月
Owner YANTAI UNIV
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