Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Arylamine nitrogen mustard derivative N,N-bis(2-chloroethyl)-N'-acetyl-1,4-phenylenediamine and preparation method thereof

A technology of arylamine nitrogen mustard and chloroethyl, which is applied in the preparation of carboxylic acid amides, amino compounds, organic compounds, etc., can solve the problems of blocking and killing, reducing the body's defense function, etc., and achieve enhanced therapeutic index, Reduce the risk of complications and reduce the effect of toxic side effects

Inactive Publication Date: 2017-05-10
CHANGAN UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Nitrogen mustards are commonly used anti-tumor drugs with particularly good anti-tumor activity. However, as traditional cytotoxic drugs, they still have the unique disadvantages of bioalkylating agents. At the same time, it also has an inhibitory effect on other normal cells that proliferate rapidly, for example, it also has the effect of blocking and killing some bone marrow cells, intestinal epithelial cells, and some hair cells, which will cause nausea, vomiting, Hair loss and other serious adverse reactions; in addition, nitrogen mustard drugs also have immunosuppressive effects, which will reduce the body's defense function, allowing bacteria and viruses to enter and cause various infections

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Arylamine nitrogen mustard derivative N,N-bis(2-chloroethyl)-N'-acetyl-1,4-phenylenediamine and preparation method thereof
  • Arylamine nitrogen mustard derivative N,N-bis(2-chloroethyl)-N'-acetyl-1,4-phenylenediamine and preparation method thereof
  • Arylamine nitrogen mustard derivative N,N-bis(2-chloroethyl)-N'-acetyl-1,4-phenylenediamine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0039] The preparation method of arylamine nitrogen mustard derivative N,N-bis(2-chloroethyl)-N'-acetyl-1,4-phenylenediamine comprises the following steps:

[0040] Step 1, preparing N,N-bis(2-chloroethyl)-1,4-phenylenediamine;

[0041] Substep 1a, first prepare N,N-di(2-hydroxyethyl)-4-nitroaniline according to the following steps: 4-chloronitrobenzene, diethanolamine, potassium carbonate and 1% CuSO 4Add the solution into the reactor one by one, stir evenly, when the temperature rises to 82°C, add toluene into the reactor, continue to heat up to 115-120°C, keep stirring at a constant temperature for 6-9 hours, after the reaction is complete, remove the toluene by distillation, distill The final mother liquor was poured into hot water at 40°C-60°C, stirred, and after standing overnight, the water layer was suction filtered to obtain the crude product, which was recrystallized with absolute ethanol to obtain yellow needle-shaped crystals N,N-di( 2-Hydroxyethyl)-4-nitroaniline...

Embodiment 1

[0046] 1.1 Synthesis of N,N-bis(2-hydroxyethyl)-4-nitroaniline

[0047]

[0048] Add 12.64g (0.080mol) of 4-chloronitrobenzene, 10.99g (0.104mol) of diethanolamine and 7.18g (0.052mol) of potassium carbonate to a 250mL three-necked flask, and finally add 1.2mL of CuSO with a mass concentration of 1%. 4 solution, mix well. Heat to raise the temperature. When the temperature reaches 82°C, add 5.0mL of toluene to the reaction liquid, continue to raise the temperature to control the reaction temperature to 117°C, use thin-layer chromatography to track the reaction progress, and stir at constant temperature for 6h. After the reaction is complete, remove the toluene by distillation, pour the distilled mother liquor into hot water at 40°C, stir vigorously, let it stand overnight, and remove the water layer by suction filtration to obtain the crude product, which is recrystallized with absolute ethanol to obtain a yellow needle Crystalline N,N-bis(2-hydroxyethyl)-4-nitroaniline 11...

Embodiment 2

[0059] 1.1 Synthesis of N,N-bis(2-hydroxyethyl)-4-nitroaniline

[0060]

[0061] Add 4-chloronitrobenzene, diethanolamine and potassium carbonate at a molar ratio of 1:1.2:0.6 to a 250mL three-necked flask, and finally add CuSO with a mass concentration of 1%. 4 solution, and the mass concentration is 1% CuSO 4 The dosage ratio of the solution to 4-chloronitrobenzene is 0.5mL:3g, mix well; heat up the temperature, when the temperature reaches 82°C, add toluene to the reaction solution, and the dosage of toluene and 4-chloronitrobenzene The ratio was 1mL:2g; continue to increase the temperature to control the reaction temperature to 120°C, use thin-layer chromatography to track the reaction progress, and stir the reaction at constant temperature for 9h. After the reaction is complete, toluene is removed by distillation, and the mother liquor after distillation is poured into hot water at 60°C, stirred vigorously, left to stand overnight, and the water layer is removed by su...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
boiling pointaaaaaaaaaa
Login to View More

Abstract

The invention specifically discloses a structural formula of an arylamine nitrogen mustard derivative N,N-bis(2-chloroethyl)-N'-acetyl-1,4-phenylenediamine and a preparation method of the derivative. The method comprises the following steps: preparing N,N-bis(2-chloroethyl)-1,4-phenylenediamine; filling a reactor with N,N-bis(2-chloroethyl)-1,4-phenylenediamine, dichloromethane and triethylamine, cooling in an ice-water bath, stirring, dropwise adding a mixed solution of acetyl chloride and dichloromethane into the reactor, removing the ice-water bath after dropwise adding, reacting at the room temperature for 2-14 hours, washing, drying and distilling after the reaction is completed, purifying the distilled filter cake, thereby obtaining the product. The arylamine nitrogen mustard derivative disclosed by the invention can effectively reduce the toxic or side effects of nitrogen mustard on the premise of enhancing the therapeutic index of the nitrogen mustard and has the curative effects of sterilizing and diminishing inflammation so as to reduce the risk of causing complications due to decrease in immunity after chemotherapy of a patient.

Description

technical field [0001] The invention relates to the technical field of nitrogen mustard antitumor drugs, in particular to N,N-bis(2-chloroethyl)-N'-acetyl-1,4-phenylenediamine, an arylamine nitrogen mustard derivative, and its preparation method. Background technique [0002] Nitrogen mustards are commonly used anti-tumor drugs with particularly good anti-tumor activity. However, as traditional cytotoxic drugs, they still have the unique disadvantages of bioalkylating agents. At the same time, it also has an inhibitory effect on other fast-proliferating normal cells, such as some bone marrow cells, intestinal epithelial cells, and some hair cells, which can cause nausea, vomiting, Hair loss and other serious adverse reactions; in addition, nitrogen mustard drugs also have an immunosuppressive effect, which will reduce the body's defense function, allowing bacteria and viruses to enter and cause various infections. [0003] Nitrogen mustard anti-tumor drugs are composed of ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/43C07C231/02A61P35/00A61P29/00A61P31/00
CPCC07C209/325C07C209/74C07C213/02C07C231/02C07C233/43
Inventor 李春荣李发明邓红章郭靖茹王广华姬雨
Owner CHANGAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com