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Synthetic method of nitrogen mustard-glycerol phosphatidyl choline compound

A technology of glycerol phosphatidylcholine and synthesis method, which is applied in the field of drug synthesis, can solve the problems of low reaction efficiency, high reaction temperature, and long time, and achieve the effects of solvent saving, short reaction time, and mild reaction conditions

Inactive Publication Date: 2014-09-03
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the synthesis methods of nitrogen mustard-glycerol phosphatidylcholine compound are mainly acid anhydride method and acid chloride method, the reaction temperature is higher, the time is longer, and the reaction efficiency is lower

Method used

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  • Synthetic method of nitrogen mustard-glycerol phosphatidyl choline compound
  • Synthetic method of nitrogen mustard-glycerol phosphatidyl choline compound
  • Synthetic method of nitrogen mustard-glycerol phosphatidyl choline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of Compound I

[0025]

[0026] In round bottom flask, add benzoic acid mustard (1mol), CDI (0.5mol), dichloromethane is made solvent, room temperature reaction 0.5 hour, after TLC (thin layer chromatography) shows that reaction is finished, adds GPC (0.2 mol) in the system. mol) and DBU (0.8mol), reacted for 1 hour, TLC showed that after the reaction was completed, a white or yellowish product was obtained by precipitation and column separation, with a yield of 90%.

Embodiment 2

[0028] Synthesis of Compound II

[0029]

[0030] Add chlorambucil (1mol), CDI (1.3mol) and THF as solvent in the round bottom flask, react at room temperature for 1 hour, after TLC shows that the reaction is complete, add GPC (0.2mol) and DBU (1.1mol) to the system ), reacted for 4 hours, TLC showed that after the reaction was completed, a white or off-yellow product was obtained by precipitation and column separation, and the yield was 80%.

Embodiment 3

[0032] Synthesis of Compound I

[0033] In the round bottom flask, add benzoic acid mustard (1mol), CDI (1mol), and ethylene dichloride is used as solvent, react at room temperature for 3 hours, after TLC shows that the reaction is complete, add GPC (0.5mol) and DBU (1mol) in the system ), reacted for 3 hours, TLC showed that after the completion of the reaction, a white or off-yellow product was obtained by precipitation and column separation, and the yield was 92%.

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Abstract

The invention discloses a synthetic method of a nitrogen mustard-glycerol phosphatidyl choline compound. The synthetic method comprises the following step of reacting at room temperature by taking a nitrogen mustard-type compound and glycerol phosphatidyl choline as raw materials, taking N, N'-carbonyldimidazole and 1, 8-diazabicyclo C11-7-alkene and taking an aprotic solvent as a reaction solvent, thereby preparing the nitrogen mustard-glycerol phosphatidyl choline compound. The method disclosed by the invention is simple to operate, is mild in reaction condition, and is high in yield.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and relates to a synthesis method of nitrogen mustard-glycerol phosphatidylcholine compound. Background technique [0002] The nitrogen mustard-glycerol phosphatidylcholine compound is a new type of compound formed by linking the alkylated part of the nitrogen mustard drug as a hydrophobic tail and a phospholipid hydrophilic head through a covalent bond. Their antitumor activity and liposome-forming properties hold great potential for development in the field of cancer therapy. At present, the synthetic methods of nitrogen mustard-glycerol phosphatidylcholine compound are mainly acid anhydride method and acid chloride method, the reaction temperature is higher, the time is longer, and the reaction efficiency is lower. Therefore, it is necessary to invent new methods and techniques to prepare high-yield nitrogen mustard-glycerol phosphatidylcholine compounds. [0003] N,N'-Carbonyldii...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/10A61P35/00
Inventor 李新松方硕
Owner SOUTHEAST UNIV
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