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Heterocyclic-fused naphthalimide and preparation method and application thereof

A reaction and cycloalkyl technology, applied in the field of fluorescent dyes, can solve the problems that the accuracy of detection is easily affected by changes in probe concentration, wide detection range, and fluctuations, and achieve good chemical/photostability and strong specificity , the effect of high yield

Inactive Publication Date: 2013-01-23
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the response of most fluorescent molecular probes to pH is based on the increase or decrease of fluorescence intensity, and its detection accuracy is easily affected by changes in probe concentration and fluctuations in light sources and detectors, and may also be affected by non-target molecules in complex systems. and other factors such as the environment
In addition, most pH probes have the problem of wide detection range

Method used

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  • Heterocyclic-fused naphthalimide and preparation method and application thereof
  • Heterocyclic-fused naphthalimide and preparation method and application thereof
  • Heterocyclic-fused naphthalimide and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1, the synthesis of heterocyclic naphthalimide (ENNA)

[0047] Heterocyclic naphthalimide (ENNA) (R 1 for -(CH 2 ) 2 OH,R 2 , R 3 , R 4 , R 5 or R 6 Both are H), the chemical name is: N-hydroxyethyl-4H-1,2,4-triazole (1,5-a) diazacyclo-1,8-naphthalimide synthetic route is as follows :

[0048]

[0049] 1. N-hydroxyethyl-4-bromo-1,8-naphthalimide (B 1 )Synthesis

[0050]

[0051] Add 2g (7.22mmol) 4-bromo-1,8-naphthalic anhydride (A) into a 250ml single-necked round bottom bottle, add 160ml of ethanol and heat to reflux. After heating and stirring for a while, cool to 50°C, slowly add 440 μl of ethanolamine (7.3 mmol) in 5 ml of ethanol solution dropwise, heat up to reflux after dripping, the cloudy solution becomes clear at once, continue to reflux for 1 hour, the reaction ends, and solids precipitate out after cooling , suction filtration, the solid was washed three times with water and ethanol, and dried to obtain compound B (off-white soli...

Embodiment 2

[0059] Embodiment 2, the synthesis of heterocyclic naphthalimide (BNNA)

[0060] And heterocyclic BNNA (R 1 for -(CH 2 ) 3 CH 3 , R 2 , R 3 , R 4 , R 5 or R 6 Both are H) chemical name: N-butyl-4H-1,2,4-triazole (1,5-a)diazacyclo-1,8-naphthalimide, the synthetic route is as follows:

[0061]

[0062] 1. N-butyl-4-bromo-1,8-naphthalimide (B 2 )Synthesis

[0063]

[0064] Add 1.5g (5.42mmol) of 4-bromo-1,8-naphthalic anhydride (A) into a 250ml single-necked round bottom bottle, add 120ml of ethanol and heat to reflux. After heating and stirring for a while, cool to 50°C, slowly add 400 μl n-butylamine (5.6 mmol) in 5 ml ethanol solution dropwise, and heat up to reflux after dropping, the turbid solution becomes clear at once, the color deepens, turns orange, and continues to reflux After 40 minutes, the reaction was completed, and the precipitate was precipitated by adding water, filtered by suction, washed three times with water and ethanol respectively, and dr...

Embodiment 3

[0074] Embodiment 3, the synthesis of heterocyclic naphthalimide (HNNA)

[0075] And heterocyclic HNNA (R 1 for -(CH 2 ) 5 COOH, R 2 , R 3 , R 4 , R 5 or R 6 Both are H): N-hexanoyl-4H-1,2,4-triazole (1,5-a)diazacyclo-1,8-naphthalimide synthetic route is as follows:

[0076]

[0077] 1. N-hexanoyl-4-bromo-1,8-naphthalimide (B 3 )Synthesis

[0078]

[0079] Add 1.5g (5.42mmol) of 4-bromo-1,8-naphthalene dicarboxylic anhydride (A) in a 250ml single-port round bottom bottle, and 0.74mg of 6-aminocaproic acid (5.6mmol), then add 100ml of ethanol and heat to In the reflux state, when the reaction solution changes from the initial milky white turbid liquid to a brown clear liquid, the reaction is completed, cooled, added water to precipitate the precipitate, filtered with suction, washed the solid with water and ethanol three times, and dried to obtain compound B 3 (off-white solid B 3 ), weighing 1.08g, yield 50.9%, the temperature of the above-mentioned reflux is ...

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Abstract

The invention discloses a heterocyclic-fused naphthalimide and a preparation method and application thereof. The preparation method of the compound provided by the invention comprises the following steps: 1) 4-bromine-1, 8-naphthalic anhydride and an N-R1 compound are reacted in a solvent A to obtain a compound B; and 2) the compound B obtained in step 1), 1, 2, 4-triazole and K2CO3 are reacted in a solvent B, and the reaction liquid is collected to obtain the compound disclosed in formula (I). An experiment in the invention proves that the compound prepared in the method disclosed by the invention can be used as a naphthalimide fluorescent probe used for monitoring pH, can be used for sensitively monitoring the subtle change of the pH under a physiological condition in a water solution with the pH of 5.5-7.5, and has a narrow range of response.

Description

technical field [0001] The invention relates to fluorescent dyes, in particular to a heterocyclic naphthalimide and its preparation method and application. Background technique [0002] l, 8-Naphthimide is an excellent precursor for the synthesis of fluorescent probes. It has good photostability, high fluorescence quantum yield, moderate fluorescence emission wavelength and large Stokes shift. It is widely used In many fields, fluorescent molecular probes with different effects can be designed and synthesized by modifying the N- and 4-positions. [0003] With the application of various natural and synthetic fluorescent probes and the emergence of new instruments such as microscopes and flow cytometers, fluorescence analysis methods have been widely used in life sciences. Detecting microenvironmental changes of substances related to biological systems has become an important research field. Among them, pH plays an important basis for judgment in physiological and pathologic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/16C09K11/06G01N21/64
Inventor 上官棣华周进刘祥军方灿良
Owner INST OF CHEM CHINESE ACAD OF SCI
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