1,8-naphthoylamido(2-R-acridinyl)thiourea silver ion probe and preparation method thereof

A technology based on acridine group and naphthyl amide group is applied in 1 field and achieves the effects of simple and easy preparation method, high yield, and convenience for use and storage

Active Publication Date: 2018-07-06
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are few effective silver ion-selective fluorescent probes, so it is very meaningful to develop high-sensitivity colorimetric and fluorescent probes for Ag+ detection

Method used

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  • 1,8-naphthoylamido(2-R-acridinyl)thiourea silver ion probe and preparation method thereof
  • 1,8-naphthoylamido(2-R-acridinyl)thiourea silver ion probe and preparation method thereof
  • 1,8-naphthoylamido(2-R-acridinyl)thiourea silver ion probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation method of 1,8-naphthylamide (2-methoxyacridinyl) thiourea includes the following steps:

[0029] Step 1. Add 1.94g of 1,8-naphthalene anhydride and 95mL of DMF into a three-necked flask. Add 6.93g of hydrazine hydrate dropwise under stirring. Heat at 105°C for 3.5h. After the reaction, immerse in water to precipitate The yellow solid was washed with distilled water, filtered with suction, and dried to obtain a golden yellow powder, namely N-amino-1,8-naphthimide.

[0030] Step 2. Add 0.05g of N-amino-1,8-naphthimide, 20mL of acetonitrile or absolute ethanol or methanol into the round bottom flask, and add 0.092g of 2-methoxy- 7-Acridine isothiocyanate was refluxed and stirred at 75°C for 11.5h. After the reaction was monitored by TCL, filtered while hot, and the filtered solid was washed with a detergent at 75°C to obtain 1, 8-naphthylamide (2 -Methoxyacridinyl)thiourea.

Embodiment 2

[0032] The preparation method of 1,8-naphthylamide (2-methoxyacridinyl) thiourea includes the following steps:

[0033] Step 1. Add 2.04g of 1,8-naphthalene anhydride, 105mL of DMF into a three-necked flask, add 7.23g of hydrazine hydrate dropwise under stirring, heat at 115℃ for 4.5h, after the reaction is immersed in water to precipitate The yellow solid was washed with distilled water, filtered with suction, and dried to obtain a golden yellow powder, namely N-amino-1,8-naphthimide.

[0034] Step 2. Add 0.15g of N-amino-1,8-naphthimide, 30mL of acetonitrile or absolute ethanol or methanol into a round bottom flask, and then add 0.551g of 2-methoxy- 7-Acridine isothiocyanate, reflux and stir at 85°C for 12.5h. After the reaction is monitored by TCL, filter while hot, and wash the filtered solid with a detergent at 85°C to obtain 1, 8-naphthylamide (2 -Methoxyacridinyl)thiourea.

Embodiment 3

[0036] The preparation method of 1,8-naphthylamide (2-methoxyacridinyl) thiourea includes the following steps:

[0037] Step 1. Add 1.99g of 1,8-naphthalene anhydride and 100mL of DMF into a three-necked flask. Add 6.98g of hydrazine hydrate dropwise under stirring. Heat at 110°C for 4h. After the reaction, immerse in water to precipitate yellow. The solid was washed with distilled water, filtered with suction, and dried to obtain a golden yellow powder, namely N-amino-1,8-naphthoyl, with a yield of 82%, mp260-263°C.

[0038] Step 2. Add 0.1g of N-amino-1,8-naphthimide, 25mL of acetonitrile or absolute ethanol or methanol in a round bottom flask, and then add 0.242g of 2-methoxy- 7-Acridine isothiocyanate was refluxed and stirred at 80°C for 12h. After the reaction was monitored by TCL, it was filtered while hot. The filtered solid was washed with a detergent at 80°C to obtain 1,8-naphthylamide (2- An orange-yellow powder solid of methoxyacridinyl)thiourea, the yield is 55.96%, mp...

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Abstract

The invention discloses a 1,8-naphthoylamido(2-R-acridinyl)thiourea silver ion probe of which the chemical structural formula is as shown in the formula (II) in the description, wherein the R group ismethyl or methoxyl. The invention also provides a preparation method of the 1,8-naphthoylamido(2-R-acridinyl)thiourea silver ion probe. The 1,8-naphthoylamido(2-R-acridinyl)thiourea prepared by the preparation method provided by the invention has very high selectively to silver ions when being used for a fluorescent probe; and furthermore, the preparation method of the 1,8-naphthoylamido(2-R-acridinyl)thiourea, provided by the invention, is simple and easy, is high in yield and low in cost and has good popularization prospects.

Description

Technical field [0001] The invention relates to the technical field of organic fluorescent probes. More specifically, the present invention relates to a 1,8-naphthylamide (2-R acridinyl) thiourea silver ion probe and its preparation method. Background technique [0002] Metal ions are closely related to environmental sciences, life sciences, medicine and other fields, and their identification and detection also occupy an important position in analytical chemistry. Silver ion is one of the heavy metal ions that are threatening and harmful to the human body and the environment. Long-term exposure of humans or animals to the silver environment can cause anemia, heart dilation, slow growth, embryo toxicity, and liver cirrhosis. Because silver is widely used in industrial production processes such as electroplating, metallurgy, military industry, etc., the detection of silver ions and the study of biological processes have become research hotspots in recent years. Fluorescent probe...

Claims

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Application Information

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IPC IPC(8): C07D401/12C09K11/06G01N21/64
CPCC07D401/12C09K11/06C09K2211/1029G01N21/643
Inventor 霍丽妮陈睿李培源贾智若韦燕飞卢澄生
Owner GUANGXI UNIV OF CHINESE MEDICINE
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