Double-addition fulleropyrrolidine and preparation method thereof

A technology of fullerene pyrrolidine and double addition, applied in the direction of organic chemistry, can solve the problems of limited research and application, limited solubility, etc., and achieve the effect of avoiding aggregation and improving solubility

Inactive Publication Date: 2014-06-25
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the strong lipophilicity of the carbon cage structure of fullerene, its solubility in polar solvents such as water is very limited, which limits its research and application in biological systems.

Method used

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  • Double-addition fulleropyrrolidine and preparation method thereof
  • Double-addition fulleropyrrolidine and preparation method thereof
  • Double-addition fulleropyrrolidine and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0026] Embodiment 1 double addition fullerene pyrrolidine

[0027] 1. Synthesis of N-substituted benzyl aminoacetate - Ammonolysis

[0028] In a 250mL three-neck round bottom flask with a dropping funnel, under magnetic stirring and nitrogen protection, add 2.5 mL (25 mmol) 2-(2-aminoethoxy) ethanol and add 90 mL CH 2 Cl 2 Diluted 2.5 mL of triethylamine, added dropwise in 1 h at 0°C with 10 mL of CH 2 Cl 2 Dissolve and dilute 2.5 mL (15.9 mmol) benzyl 2-bromoacetate, stir at room temperature for 4 hours, then extract the organic phase with distilled water 3 times (100 mL / time), and saturated saline for 3 times (80 mL / time), with anhydrous Na 2 SO 4 Dry overnight, filter and rotary evaporate to dryness, over SiO 2 Silica gel column (100-200 mesh), 99:1 v / v ethyl acetate / methanol for elution, collected the desired components, rotary evaporation, and vacuum drying to obtain a gray-yellow viscous oily compound, namely benzyl N-substituted aminoacetate (1.5 g, 37% yield)...

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Abstract

The invention discloses double-addition fulleropyrrolidine and a preparation method thereof, relating to the field of medicinal chemistry. Double-addition N-substituted fulleropyrrolidine is obtained by introducing two water-soluble ethylene glycol arms on a fullerene molecule through cycloaddition, so that not only is the solubility increased, but also the double-addition N-substituted fulleropyrrolidine can be prevented from being aggregated and can be more uniformly dispersed in a water solution. The double-addition fulleropyrrolidine has the structural formula as shown in the specification. The problems that the traditional fullerene is poor in biocompatibility and single-addition fulleropyrrolidine is easy to aggregate are effectively solved.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a double-addition fullerene pyrrolidine and a preparation method thereof. Background technique [0002] [60] Fullerene molecule is a closed network cage structure formed by 60 carbon atoms self-combined. It has been found through research that fullerene has the functions of scavenging free radicals, cleaving DNA, inhibiting HIV activity, killing tumor cells, Biological effects such as protecting nerves. Since the entire cage is completely composed of approximately sp 2 Composed of hybridized carbon atoms, it has strong electrophilic ability, and the efficiency of generating singlet oxygen after photoexcitation is as high as 100%. The active oxygen is highly reactive and can exhibit obvious cytotoxicity; C60 is extremely easy The electrochemical properties of reacting with free radicals produced by biological systems are called "sponges absorbing free radicals", which can be u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/08
CPCC07D487/10
Inventor 张静李园
Owner ZHENGZHOU UNIV
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