N-aryl pyridine thiazolothiazole-cucurbituril compound as well as preparation method and application thereof

A technology of arylpyridinethiazole and cucurbituril, which is applied in the field of nanozymes, to achieve precise controllability, good application prospects, and avoid background interference and biological body damage

Active Publication Date: 2022-03-25
ZHENGZHOU UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above-mentioned technical problems, the present invention proposes a kind of N-arylpyridinethiazolothiazole-cucurbituril compound and its preparation method, in order to solve the prior art There is no research on the enzymatic activity of thiazolothiazole derivatives in

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  • N-aryl pyridine thiazolothiazole-cucurbituril compound as well as preparation method and application thereof
  • N-aryl pyridine thiazolothiazole-cucurbituril compound as well as preparation method and application thereof
  • N-aryl pyridine thiazolothiazole-cucurbituril compound as well as preparation method and application thereof

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preparation example Construction

[0049] A preparation method of N-arylpyridinethiazolothiazole-cucurbituril complex, comprising the steps of:

[0050] S1. According to the report of the document "Thiazolothiazole Fluorophores ExhibitingStrong Fluorescence and Viologen-Like Reversible Electrochromism" published on JACS, synthesize 2,5-bis(4-pyridyl)thiazolothiazole, the 2,5-bis(4-pyridine base) thiazolothiazole as an intermediate, which is dissolved in 2,4-dinitrofluorobenzene, and 2,5-bis(4-pyridyl)thiazolothiazole and 2,4-dinitrofluoro The molar ratio of benzene is 1:(42-85), then heated at 90°C for 48 h, cooled, washed three times with n-hexane, and vacuum-dried to obtain Zincke salt, that is, N-aryl or N-alkylpyridinium salt;

[0051] S2. the Zincke salt obtained in step S1 and p-chloroaniline are placed in a round-bottomed flask according to a molar ratio of 1:(2-4), add 20 mL of ethanol and water and mix, wherein the volume ratio of ethanol and water is 3 : 2, then heated to reflux at 100°C for 48 h, af...

Embodiment 1

[0053] Example 1, 0.126 g of Zincke salt, 0.153 g of p-chloroaniline, 12 mL of ethanol and 8 mL of water were placed in a 100 mL round bottom flask. The reaction mixture was refluxed at 100 °C for 48 h. After the reaction was completed, it was washed with ether, and the obtained crude product was recrystallized in methanol solution to obtain pure grass-green N-arylpyridinium salt (38.6 mg, 33.7% yield).

[0054] 1 H NMR (600 MHz, D 2 O): δ 9.19 (d, J = 6.4 Hz, 4H), 8.75 (d, J = 6.6Hz, 4H), 7.73 (d, J = 2.8 Hz, 8H).

[0055] 0.126 g of Zincke's salt, 0.0765 g of p-chloroaniline, 12 mL of ethanol and 8 mL of water were placed in a 100 mL round bottom flask. The reaction mixture was refluxed at 100 °C for 48 h. After the reaction is completed, wash with ether, and recrystallize the obtained crude product in a methanol solution to obtain a pure grass-green N-arylpyridinethiazolothiazole molecule.

[0056] N-arylpyridinethiazolothiazole molecules and cucurbituril 8 were respec...

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Abstract

The invention provides a preparation method of an N-aryl pyridine thiazolothiazole-cucurbituril compound, which comprises the following steps: dissolving 2, 5-bis (4-pyridyl) thiazolothiazole in 2, 4-dinitrofluorobenzene, heating, cooling, washing with n-hexane, and carrying out vacuum drying to obtain a Zincke salt; the preparation method comprises the following steps: adding ethanol and water into Zincke salt and parachloroaniline, uniformly mixing, heating and refluxing, cleaning with diethyl ether, and recrystallizing an obtained crude product in a methanol solution to obtain N-aryl pyridine thiazolothiazole molecules; the molecule and cucurbituril 8 are respectively dissolved by dimethyl sulfoxide and then are mixed to prepare a storage solution. The oxidoid enzyme activity of the thiazolothiazole derivative is found for the first time, and the compound and macrocyclic molecule cucurbituril are self-assembled, so that the photoinduced oxidase activity of N-aryl pyridine thiazolothiazole is greatly improved, and the nano compound with excellent photoinduced oxidase activity is constructed. And the method has a better application prospect in nano-enzyme biological treatment and sensing.

Description

technical field [0001] The invention relates to the technical field of nanozymes, in particular to an N-arylpyridinethiazolothiazole-cucurbituril complex and a preparation method and application thereof. Background technique [0002] Nanozymes are a class of nanomaterials with similar catalytic activity and kinetic characteristics of natural enzymes. Compared with natural enzymes, nanozymes have good stability, easy preparation and synthesis, controllable and adjustable enzyme activity and other properties, and have attracted increasing attention in practical applications. The development of highly active enzyme-like lead compounds is a hot spot in the field of nanozyme research. [0003] Thiazolothiazole derivatives are a new class of organic molecules discovered for the first time in 2017. These molecules have excellent photochromic and electrochemical catalytic activities, and have attracted everyone's attention in the field of batteries. However, there is no report abo...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07D513/04B01J31/02B01J35/00G01N21/33G01N21/78A61L2/08
CPCC07D513/04C07D487/22B01J31/003B01J31/0244B01J31/0249G01N21/33G01N21/78A61L2/088B01J35/39
Inventor 杨冉孙远强豆优李朝辉屈凌波
Owner ZHENGZHOU UNIV
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