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4'-pyridylpyrimidine compound and synthetic method and application thereof

A kind of technology of pyridyl pyrimidine and synthesis method, which is applied in the field of fine organic synthesis and achieves the effect of good practicability

Inactive Publication Date: 2017-12-05
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, no 4′-pyridylpyrimidine compound has been synthesized and used for Cu 2+ Related reports on ion detection

Method used

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  • 4'-pyridylpyrimidine compound and synthetic method and application thereof
  • 4'-pyridylpyrimidine compound and synthetic method and application thereof
  • 4'-pyridylpyrimidine compound and synthetic method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0029] The synthetic method of 4'-pyridyl pyrimidine compound, synthetic process is:

[0030]

[0031] Specific steps are as follows:

[0032] 1) Preparation of 7-(pyridin-4'-yl-methylene) isolongifanone:

[0033] Put 8mmol of isolongifolanone, 12mmol of 4-pyridinecarbaldehyde, 16mmol of sodium ethoxide and 30mL of ethanol in a three-necked flask equipped with a stirrer, a thermometer and a reflux condenser in sequence, and heat it to reflux at 80-90°C to react for 5 hours From about to isolonganone, the conversion rate reaches over 95% (GC tracking detection). The reactant was extracted 3 times with 25 mL of ethyl acetate, the organic phases were combined, and then washed several times with saturated brine until neutral, and the organic phase was dried with anhydrous sodium sulfate; the solvent was recovered by filtration and concentration to obtain 7-(pyridine-4 '-yl-methylene) isolongifolanone; carry out recrystallization with ethanol-ethyl acetate, obtain colorless an...

Embodiment 2

[0037] The 6,6,10,10-tetramethyl-4-(pyridin-4'-yl)-5,7,8,9,10,10a-hexahydro-6H-6a,9- Endomethylenebenzo-2-quinazolinamine formulated as 1 × 10 -5 M's HEPES buffer solution (20mM, pH=7.2, 80% (v / v) C 2 h 5 OH), the Cu 2+ Ions were formulated with the same HEPES buffer at a concentration of 0.1 to 1.0×10 -4 M's solution. Measured different concentrations of Cu 2+ Ion pair 6,6,10,10-tetramethyl-4-(pyridin-4′-yl)-5,7,8,9,10,10a-hexahydro-6H-6a,9-methanomethene The fluorescence intensity of benzo-2-quinazolinamine, then carry out linear fitting to the fluorescence intensity at 450nm place, obtain as figure 1 The straight line shown, further calculated by the formula, the detection limit of the compound for copper ions is as low as 4×10 -8 M.

Embodiment 3

[0039] 6,6,10,10-tetramethyl-4-(pyridin-4′-yl)-5,7,8,9,10,10a-hexahydro-6H-6a,9-methanobenzene And-2-quinazolinamine was dissolved in pure ethanol to prepare a concentration of 1×10 -5 The solution of M, its solution is colorless and transparent under fluorescent lamp, with 1.5×10 -4 The addition of different metal ions of M, the color of the solution did not change significantly, and then observed under a 365nm ultraviolet lamp, as figure 2 As shown, adding Cu 2+ The blue fluorescence of the solution of ions has disappeared, and by adding the same amount of other metal ions, such as Hg 2+ ,Al 3+ , Ag + ,La 3+ ,Pb 2+ , Fe 3+ , Fe 2+ ,Cr 3+ ,Co 2+ ,Zn 2+ Plasma contrast, the fluorescence of the compound did not change significantly, indicating that the compound can be used as an effective identification of Cu 2+ Ionic fluorescent probes.

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Abstract

The invention discloses a 4'-pyridylpyrimidine compound and a synthetic method and application thereof. By using a derivative iso-longitolanone of natural renewable resource turpentine as a raw material, a novel 4'-pyridylpyrimidine compound is prepared. Iso-longitolanone and 4-pyridylaldehyde are subjected to condensation to generate 7-(pyridine-4'-yl-methylene)iso-longitolanone; 7-(pyridine-4'-yl-methylene)iso-longitolanone and guanidine hydrochloride are subjected to condensation and cyclization to obtain a 4'-pyridylpyrimidine compound 6,6,10,10-tetramethyl-4-(pyridine-4'-yl)-5,7,8,9,10,10a-hexahydro-6H-6a,9-methanobenzo-2-quinazolinamine. The compound can specifically recognize copper ion, can be specifically complexed with Cu<2+> ion and generates quenching of blue fluorescence. Thus, the compound can be used as a fluorescence probe for detection of copper ion and has good practicality.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a 4'-pyridylpyrimidine fluorescent probe, a preparation method thereof and a fluorescence detection for copper ions. It specifically relates to 4'-pyridyl pyrimidine compounds, their synthesis method and application. Background technique [0002] Cu 2+ It is one of the essential trace elements for the human body, and it usually exists in the form of copper protein in the human body. It is a very important biocatalyst, and it plays a very important role in the human body's hematopoiesis, softening of blood vessel walls and hormone secretion. Excessive intake and enrichment of copper ions will lead to chronic poisoning of the human body and severe damage to the liver and other organs. In the past, due to the shortcomings of low sensitivity and complicated operation, the conventional analysis and detection methods could not detect the copper ions in the organism effe...

Claims

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Application Information

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IPC IPC(8): C07D401/04C09K11/07G01N21/64
Inventor 王石发王忠龙谷文徐徐杨益琴徐海军匡红波杨丽娟姜倩张燕刘艳芳
Owner NANJING FORESTRY UNIV
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