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O-nitro aryl nitrogen mustard derivative and preparation methods and application thereof

A technology for nitroaroyl mustard and derivatives, which is applied in the field of o-nitroaroyl mustard derivatives, can solve the problems of low selectivity, high toxicity, and many adverse reactions of nitrogen mustard compounds, and achieves improved selectivity. , easy handling, and cheap reagents

Inactive Publication Date: 2012-09-19
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, nitrogen mustard compounds have problems such as many adverse reactions, high toxicity, and low selectivity.

Method used

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  • O-nitro aryl nitrogen mustard derivative and preparation methods and application thereof
  • O-nitro aryl nitrogen mustard derivative and preparation methods and application thereof
  • O-nitro aryl nitrogen mustard derivative and preparation methods and application thereof

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Embodiment Construction

[0016] Two different alternative preparation methods of o-nitroaroyl mustard derivatives of the present invention are given below:

[0017] The first preparation method of the compound of the present invention is to use sodium carbonate as an acid-binding agent, heat and stir the acid chloride in dry acetone, and drop the acetone solution of diethanolamine. Reflux for 10 h, evaporate acetone to dryness, add distilled water to dissolve, extract with ethyl acetate three times, combine extracts, concentrate, and perform silica gel column chromatography. The dihydroxy compound is obtained. Then react the obtained dihydroxy compound with thionyl chloride in dichloromethane to obtain the target compound.

[0018]

[0019] The second preparation method of the compound of the present invention is: dissolve diethanolamine and thionyl chloride in dichloromethane, stir in an ice bath for 3 hours, and distill off excess thionyl chloride and dichloromethane under reduced pressure to ob...

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PUM

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Abstract

The invention discloses an o-nitro aryl nitrogen mustard derivative and a preparation method and application thereof. The o-nitro aryl nitrogen mustard derivative is figured in the following formula; and in the formula, R is o-nitro phenyl or o-nitro phenoxyl. The preparation method of the o-nitro aryl nitrogen mustard derivative is that sodium carbonate is adopted as acid-binding agent, acyl chloride is subjected to reaction, extraction and silica gel column chromatography in dry acetone to obtain dihydroxy compound, and then the dihydroxy compound and thionyl chloride reacts with each other in methylene chloride to obtain the target substance. The invention further provides another preparation method of the o-nitro aryl nitrogen mustard derivative.

Description

technical field [0001] The invention relates to an organic compound, as well as a preparation method and application of the compound. More precisely, the present invention relates to a derivative of o-nitroaroyl mustard, as well as the preparation method and application of the derivative. Background technique [0002] Nitrogen mustard is one of the earliest anticancer drugs. It forms highly active ethyleneiminium ions or carbocations in the body, becoming an electrophilic strong alkylating agent, and then interacts with electron-rich groups in biological macromolecules (such as DNA, RNA or some important enzymes) Groups (such as hydroxyl, amino, carboxyl, phosphate, etc.) are covalently bonded to inactivate them or break DNA molecules, thereby achieving the purpose of anti-tumor. [0003] Nitrogen mustard compounds belong to cytotoxic drugs and are non-structurally specific anti-tumor bioalkylating agents, wherein N, N-(2-chloroethyl)amino is an anti-tumor active functiona...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/13C07C235/20C07C231/12C07C231/02A61P35/00
Inventor 贺殿杨欢邱楠楠董永喜
Owner LANZHOU UNIVERSITY
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