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P-isosulfhydryl phenyl five-membered nitrogen heterocyclic ring tetraacethyl chelate and preparation thereof

A kind of technology of isothiocyanophenyl, europium pentadecanetetraacetate, applied in the field of organic heterocyclic compound synthesis

Inactive Publication Date: 2009-01-21
INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no research reports on the chelation of its derivatives with lanthanides as time-resolved fluorescent immunoassay reagents

Method used

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  • P-isosulfhydryl phenyl five-membered nitrogen heterocyclic ring tetraacethyl chelate and preparation thereof
  • P-isosulfhydryl phenyl five-membered nitrogen heterocyclic ring tetraacethyl chelate and preparation thereof
  • P-isosulfhydryl phenyl five-membered nitrogen heterocyclic ring tetraacethyl chelate and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] N, N'-di-p-toluenesulfonyl hydroxyethyl-N, N'-di-p-toluenesulfonyl ethylenediamine (compound III)

[0041] 77g (0.4mol) of p-toluenesulfonyl chloride in 100ml of pyridine, under vigorous stirring, was added dropwise a solution of 14.8g (0.1mol) of N, N'-di(2-hydroxyethyl)ethylenediamine in 200ml of pyridine, dropwise Stir at room temperature for 3 hours. Pour the solution into 250ml of ice and 250ml of concentrated hydrochloric acid to filter, wash with water, and recrystallize from ethanol to obtain pale yellow crystals, mp: 99-100°C (70%).

Embodiment 2

[0043] N, N', N"-tri-p-toluenesulfonyldiethylenetriamine (Compound IV)

[0044] Add 10.3g (0.1mol) of diethylenetriamine to 106ml (0.4mol) of sodium hydroxide solution, and under vigorous stirring, add dropwise 57.1g (0.3mol) of p-toluenesulfonyl chloride in 375ml of diethyl ether solution at 0°C, and the addition is complete. Continue to stir for 1 hour, filter to obtain the crude product, recrystallize with ethanol, mp: 200-202 ° C (60%)

Embodiment 3

[0046] N, N', N"-tri-p-toluenesulfonyldiethylenetriamine disodium salt (Compound V)

[0047] 56.4g (0.1mol) of compound 2 was added to 13.6g (0.2mol) of sodium ethoxide and heated in 150ml of absolute ethanol solution at 80°C for 1 hour, the solvent was removed under reduced pressure, and the product was obtained by vacuum drying.

[0048] Preparation Example

[0049] Example 1

[0050] 1,4,7,10,13-penta-toluenesulfonylpentaazacyclopentadecane (compound VI)

[0051] First add 100ml of DMF, then blow nitrogen, heat at 100°C, and slowly add dropwise a solution of 76.4g (0.1mol) of compound III in 200ml of DMF and a solution of 61g (0.1mol) of compound V in 200ml of DMF while stirring. After dropping, brown The reaction solution was reacted at 100-110° C. for 3 hours. Cool, stir, pour into water, filter out the precipitate, wash with water, wash with alcohol, and recrystallize with ethanol to obtain white crystals mp: 289-290°C (document: 290-291°C, 278-280°C) (65%).

[0052]...

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Abstract

The invention relates to a chelate of isothiocyanate phenyl pentaazacyclo tetraacetic acid and a method for preparing the same. The method comprises the following steps of condensation, hydrolysis, and substitution, the product of which undergoes condensation with bromoacetate, and chelating with a lanthanide to produce p-nitrobenzene pentaazacyclo tetraacetic acid which undergoes deoxidization with 5 percent Pd / C and finally the reaction with thiophosgene to obtain the target compound I. The chelate of isothiocyanate phenyl pentaazacyclo tetraacetic acid is an unknown compound, and the formed rigid aperture compound is chelated with the lanthanide including europium, indium, scythe, and terbium, and the structure of the chelate is determined through element analysis, analysis with infrared and ultraviolet, magnetic resonance imaging, and mass spectrum, the prepared chelate is mainly used for time-resolved fluoroimmunoassay.

Description

technical field [0001] The invention belongs to the technical field of synthesis of organic heterocyclic compounds, and relates to p-isothiocyanatophenyl pentaazacyclic tetraacetic acid chelate and its preparation method and the chelate used as a homogeneous time-resolved fluorescent immunoassay reagent for immunoassay Analysis applications. Background technique [0002] The time-resolved fluorescence immunoassay has been rapidly developed and widely used because of its high sensitivity, rapidity, the use of automatic analytical instruments and the development of technology. The method uses lanthanide elements as markers to label antibodies (or antigens), oligonucleotides, biomacromolecules, target cells, etc., and then perform immune reactions of antigens and antibodies to generate immune complexes, or perform nucleic acid hybridization analysis , DNA sequence detection, etc. The principle is that lanthanide ions such as europium, samarium, terbium, and dysprosium are chel...

Claims

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Application Information

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IPC IPC(8): C07D257/00C07F5/00G01N33/52G01N33/58
Inventor 施培基王荣先王浩李美佳周晓靓傅榕赓尹鹏黄海舟吕茜茜
Owner INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI
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