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6,8-methano-tetrahydroquinazoline-2-amine schiff base iron ion fluorescence probe, and preparation method and application thereof

A technology of endomethylenetetrahydroquinazoline and endomethylenequinazoline, which is applied in the field of fine organic synthesis, and can solve the problems of not synthesizing nopinone pyridine Schiff base compounds, etc.

Inactive Publication Date: 2018-05-11
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the nopinone pyridine Schiff base compound has not been synthesized and used for Fe 3+ Related reports on ion detection

Method used

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  • 6,8-methano-tetrahydroquinazoline-2-amine schiff base iron ion fluorescence probe, and preparation method and application thereof
  • 6,8-methano-tetrahydroquinazoline-2-amine schiff base iron ion fluorescence probe, and preparation method and application thereof
  • 6,8-methano-tetrahydroquinazoline-2-amine schiff base iron ion fluorescence probe, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation method of 6,8-methanotetrahydroquinazolin-2-amine Schiff base compound is:

[0026]

[0027] Specific steps are as follows:

[0028] Preparation of 6,8-methanotetrahydroquinazolin-2-amine Schiff bases:

[0029] 2.0mmol 7,7-dimethyl-4-phenyl-5,6,7,8-tetrahydro-6,8-methanoquinazolin-2-amine, 2.4mmol pyridine-2-carbaldehyde , 2.5mmol acetic acid and 60mL ethanol were sequentially added to a three-necked flask equipped with a stirrer, a thermometer and a reflux condenser, heated to reflux for 28 hours, followed by LC-MS detection until the compound was converted again, the reaction was terminated, and the reactant was concentrated to 8mL , then cooled to room temperature, and after standing for 2 days, a pale yellow crystal 7,7-dimethyl-4-phenyl-N-(pyridine-2-methylene)-5,6,7,8-tetrahydro- 6,8-Methylenequinazolin-2-amine is compound (1), and the yield is 42%.

[0030] The product is characterized, the data are as follows:

[0031] mp:58.2-58.6℃;IR(KBr...

Embodiment 2

[0036] Compound (1) was prepared as 1×10 -4 The ethanol solution of M, all kinds of metal ions are also dissolved in ethanol to make a concentration of 1×10 -4 M's solution. Measure the fluorescence emission spectra of different metal ions to compound (1), such as figure 1 shown. The results show that with the addition of iron ions, the fluorescence intensity of the system is significantly reduced, and by adding the same amount of other metal ions, such as Mn 2+ ,Zn 2+ , K + , Ni 2+ , Ca 2+ ,Cd 2+ , Fe 2+ ,Cu 2+ , Ag + ,Co 2+ ,Cr 3+ According to plasma contrast observation, the fluorescence spectrum of the compound does not change significantly, which indicates that the compound can be used as a fluorescent probe for specifically recognizing iron ions.

[0037] Compound (2) was prepared as 1×10 -4 The ethanol solution of M, all kinds of metal ions are also dissolved in ethanol to make a concentration of 1×10 -4 M's solution. Measure the fluorescence spectrum of...

Embodiment 3

[0039] Compound (1) was prepared as 1×10 -4 M ethanol solution, dissolving iron ions in ethanol solution to make a concentration of 0~2.4×10 -4 M's solution. Measure the fluorescence emission spectra of different concentrations of iron ions to compound (1), such as image 3 shown. The results showed that with the continuous increase of iron ion concentration in the system, the fluorescence intensity of the compound decreased, which indicated that the compound could be used as a fluorescent probe for sensitive detection of iron ion.

[0040] Compound (2) was prepared as 1×10 -4 M ethanol solution, dissolving iron ions in ethanol solution to make a concentration of 0~2.4×10 -4 M's solution. Measure the fluorescence spectra of different concentrations of iron ions to compound (2), such as Figure 4 shown. The results showed that in the process of increasing the concentration of iron ions, the fluorescence intensity of the compound decreased continuously until it was comple...

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Abstract

The invention discloses a 6,8-methano tetrahydroquinazoline-2-amine schiff base iron ion fluorescence probe, and a preparation method and application thereof. A beta-pinene derivative 7,7-dimethyl-4-phenyl-5,6,7,8-tetrahydro-6,8-methano quinazoline-2-amine raw material is utilized to make condensation reaction with pyridine-2-formaldehyde and pyridine-4-formaldehyde, so that two novel 6,8-methanotetrahydroquinazoline-2-amine schiff base derivatives: 7,7-dimethyl-4-phenyl-N- (pyridine-2-methylene)-5,6,7,8-tetrahydro-6,8-methano quinazoline-2-amine (1) and 7,7-dimethyl-4-phenyl-N-(pyridine-4-methylene)-5,6,7,8-tetrahydro-6,8-methano quinazoline-2-amine (2) are obtained. The compounds (1) and (2) can be exclusively complexed with an iron ion so as to produce quenching of blue fluorescence, and thus can be used as fluorescence probes for detecting the iron ion, so as to have favorable practicability.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a 6,8-methanomethylenetetrahydroquinazoline-2-amine Schiff base iron ion fluorescent probe and a preparation method and application thereof. Background technique [0002] Fe 3+ It is an important metal ion, which is widely distributed in various living organisms and environments, and plays a vital role in human cell metabolism, enzyme reaction, oxygen transport, protein storage, etc. Free iron ions are distributed in almost all important tissues of the human body. However, lack or excess of iron ions will cause physiological disorders, such as anemia, liver function damage and Parkinson's syndrome, etc. Therefore, for Fe 3+ Specific and sensitive detection is particularly important. [0003] In recent years, various fluorophores with unique fluorescent properties have been successfully used as parent nuclei to construct Fe 3+ Organic fluorescent probes, such as: r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D401/12G01N21/64
CPCC07D401/12C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044G01N21/643G01N2021/6432
Inventor 王石发张燕王忠龙谷文徐徐杨益琴姜倩李明新匡红波
Owner NANJING FORESTRY UNIV
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