Tetrahydroquinazoline-2-schiff base compounds as well as synthesis method and application thereof

A technology of tetrahydroquinazoline and synthetic method, applied in tetrahydroquinazoline-2-amine Schiff base fluorescent probe molecule and its preparation, tetrahydroquinazoline-2-amine Schiff base compound and its synthesis, detection of zinc ions in the field of application

Inactive Publication Date: 2015-11-25
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, tetrahydroquinazolin-2-amine Schiff base compounds have not been applied to Zn 2+ detection report

Method used

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  • Tetrahydroquinazoline-2-schiff base compounds as well as synthesis method and application thereof
  • Tetrahydroquinazoline-2-schiff base compounds as well as synthesis method and application thereof
  • Tetrahydroquinazoline-2-schiff base compounds as well as synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The synthetic method of tetrahydroquinazolin-2-amine Schiff base compound, synthetic process is:

[0035]

[0036] Specific steps are as follows:

[0037] 1) Preparation of 3-benzylidene nopinone:

[0038]In a 100mL three-necked flask equipped with a thermometer, a stirrer and a reflux condenser, add 1.38g (0.01mol) nopinone, 30mL distilled water, 6.00g (0.15mol) NaOH and 1.27g (0.012mol) benzaldehyde, and heat After about 8 hours of reflux reaction, the conversion rate of nopinone reaches over 95% (GC tracking detection). After cooling, saturated brine was added to the reaction solution and extracted three times with ethyl acetate (20mL×3), the combined organic phase was washed with saturated brine until neutral, washed with anhydrous Na 2 SO 4 After drying, filtering, and concentrating, the yellow solid crude product was obtained, which was then dissolved evenly with acetone and a small amount of ethanol, and left to crystallize to obtain 1.77 g of colorless tra...

Embodiment 2

[0044] The solid 2-[[5,6,7,8-tetrahydro-4-phenyl-7,7-dimethyl-6,8-methanoquinazolin-2-imino]methyl ] Phenol compounds and different metal ions were dissolved in 4-hydroxyethylpiperazineethanesulfonic acid (HEPES) buffer solution (20mM, pH = 7.2, 50% (v / v) C 2 h 5 OH), formulated as a probe compound and Zn 2+ The concentration is 1×10 -5 Eleven solutions of M. Under the condition of excitation wavelength of 425nm, the fluorescence intensity changes in the presence of different metal ions were measured, such as figure 1 shown. The results showed that the compounds on Zn 2+ has a strong fluorescence enhancement effect, while Cu 2+ , Fe 2+ and Fe 3+ It has a strong fluorescence quenching, indicating that the compound has a strong effect on Zn 2+ Has better selectivity.

Embodiment 3

[0046] The configured 2-[[5,6,7,8-tetrahydro-4-phenyl-7,7-dimethyl-6,8-methanoquinazoline-2-imino] Methyl]phenol (1×10 -5 M)+Zn 2+ (1×10 -5 M) solution (HEPES buffer, 20mM, pH=7.2, 50% (v / v) C 2 h 5 OH) were added with Zn 2+ Equimolar amount of K + , Ca 2+ , Ni 2+ ,Fe 2+ ,Fe 3+ ,Cd 2+ ,Co 2+ ,Mn 2+ , Ag + and Cu 2+ , the fluorescence spectrum was measured under the condition of excitation wavelength of 425nm, the results are as follows figure 2 shown. When adding Cu 2+ ,Fe 2+ and Fe 3+ Ionic, 2-[[5,6,7,8-tetrahydro-4-phenyl-7,7-dimethyl-6,8-methanoquinazolin-2-imino]methanol base]phenol+Zn2+ The fluorescence intensities of 2+ >Fe 2+ >Fe 3+ , while K + , Ca 2+ , Ni 2+ ,Cd 2+ ,Co 2+ ,Mn 2+ , Ag + Plasma has little effect.

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Abstract

The invention discloses tetrahydroquinazoline-2-schiff base compounds as well as a synthesis method and an application thereof. Novel tetrahydroquinazoline-2-schiff base compounds are prepared from a raw material of nopinone which is an oxidative product of a natural renewable resource, namely beta-pinene; nopinone and benzaldehyde have a condensation reaction to generate 3-benzylidene nopinone, 3-benzylidene nopinone has a condensation and cyclization reaction with guanidine hydrochloride, 5,6,7,8-tetrahydro-4-phenyl-7,7-dimethyl-6,8-bridged methylene quinazoline-2-amino is obtained and has a condensation reaction with 2-hydroxybenzaldehyde, and 2-[[5,6,7,8-tetrahydro-4-phenyl-7,7-dimethyl-6,8-bridged methylene quinazoline-2-imine] methyl] phenol is obtained; a tetrahydroquinazoline-2-schiff base compound, namely 2-[[5,6,7,8-tetrahydro-4-phenyl-7,7-dimethyl-6,8-bridged methylene quinazoline-2-imine] methyl] phenol is taken as a specific fluorescence probe molecule and has a good application in detection of zinc ions.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to tetrahydroquinazoline-2-amine Schiff base fluorescent probe molecules, a preparation method thereof and an application in detecting zinc ions. It specifically relates to tetrahydroquinazolin-2-amine Schiff base compounds and their synthesis methods and applications. Background technique [0002] Zn 2+ It is the second most abundant transition metal element in the human body and has very important biological functions. Zn 2+ It is an important inorganic element to maintain normal life activities and is widely distributed in organisms. It exists in hundreds of enzymes and thousands of proteins in mammals. It is an important component of many enzymes and transcription factors in the body (such as carbonic anhydrase, zinc finger protein etc.), are closely related to processes such as DNA synthesis, gene expression, apoptosis, neurotransmission, signal transduction and...

Claims

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Application Information

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IPC IPC(8): C07D239/70G01N21/64
CPCC07D239/70G01N21/6428
Inventor 王石发杨金来徐海军房仙颖徐徐杨益琴芮坚曹晓琴丁志斌王芸芸
Owner NANJING FORESTRY UNIV
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