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Multi-element heterocyclic compound, preparation method thereof and application of multi-element heterocyclic compound in cysteine detection

A technology of heterocyclic compounds and cysteine, which is applied in the field of multi-component heterocyclic compounds and its preparation and its application in the detection of cysteine. Solve problems such as large organic solvents, achieve high sensitivity, stable bioluminescent signal, and high-sensitivity detection

Active Publication Date: 2019-12-20
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, there are many methods for the detection of cysteine, including methods such as colorimetry, HPLC and fluorescent probes, but the inventors of the present disclosure have found that, among these analytical methods, the detection precision of colorimetry is low; The use of organic solvents consumes a large amount of organic solvents, causing great environmental pollution, high detection costs, and it is difficult to achieve trace detection; the fluorescent probe method has disadvantages such as photobleaching and autofluorescence that cannot be ignored due to its dependence on the excitation light source. its further application

Method used

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  • Multi-element heterocyclic compound, preparation method thereof and application of multi-element heterocyclic compound in cysteine detection
  • Multi-element heterocyclic compound, preparation method thereof and application of multi-element heterocyclic compound in cysteine detection
  • Multi-element heterocyclic compound, preparation method thereof and application of multi-element heterocyclic compound in cysteine detection

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Experimental program
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Embodiment 1

[0051] The synthesis of compound shown in formula I, route is as follows:

[0052]

[0053] Proceed as follows:

[0054] Compound 1 (352mg, 2.0mmol) was placed in a round-bottomed flask, dissolved in 20mL of dichloromethane (DCM), stirred in an ice bath, triethylamine (832uL, 6.0mmol) was added, S-2 (576uL, 6.0mmol ) was dissolved in 10 mL of dichloromethane, added dropwise to the flask, and reacted at room temperature for 5 h. Compound 2 was obtained by column chromatography with a yield of 94.7%. 1 H NMR (400MHz, DMSO) δ8.30 (d, J = 9.0Hz, 1H), 8.21 (d, J = 2.3Hz, 1H), 7.55 (dd, J = 8.9, 2.4Hz, 1H), 7.26–7.14 (m,1H),6.21(dd,J=15.5,1.7Hz,1H),1.98(dd,J=6.9,1.7Hz,3H). 13 C NMR (101MHz, DMSO) δ163.94(s), 150.22(s), 149.36(s), 148.80(s), 137.43(s), 136.28(s), 125.21(s), 123.28(s), 121.01 (s), 115.94(s), 113.25(s), 18.00(s).

[0055] Compound 2 (122 mg, 0.5 mmol) was dissolved with a mixture of 8 mL of dichloromethane and methanol, and D-cysteine ​​hydrochloride dissolved ...

Embodiment 2

[0057] The synthesis of compound shown in formula II, route is as follows:

[0058]

[0059] Proceed as follows:

[0060] Compound 1 (88mg, 0.5mmol) was placed in a round bottom flask, dissolved in 5mL of dichloromethane (DCM), stirred in an ice bath, triethylamine (208uL, 1.5mmol) was added, S-1 (122uL, 1.5mmol ) was dissolved with 5mL of dichloromethane, added dropwise to the flask, and reacted at room temperature for 5h. Obtained by column chromatography (V 石油醚 :V 乙酸乙酯 =10:1~30:1) Solid compound 3, the yield was 94.8%. 1 H NMR (400MHz, DMSO) δ8.32(d, J=9.0Hz, 1H), 8.25(d, J=2.3Hz, 1H), 7.59(dd, J=9.0, 2.4Hz, 1H), 6.61(dd ,J=17.3,1.3Hz,1H),6.48(dd,J=17.3,10.2Hz,1H),6.23(dd,J=10.2,1.3Hz,1H). 13 C NMR (101MHz, DMSO) δ163.94(s), 150.02(s), 149.46(s), 137.57(s), 136.29(s), 134.34(s), 127.23(s), 125.29(s), 123.17 (s), 115.92(s), 113.23(s).

[0061] Compound 3 (115 mg, 0.5 mmol) was dissolved with a mixture of 8 mL of dichloromethane and methanol, and D-cysteine ​​hydroc...

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Abstract

The invention provides a multi-element heterocyclic compound, a preparation method thereof and an application of the multi-element heterocyclic compound in cysteine detection. The chemical structure of the multi-element heterocyclic compound is shown as a formula I. The multi-element heterocyclic compound is used as a bioluminescence probe for cysteine detection, and cysteine can be detected qualitatively and semi-quantitatively with high selectivity and high sensitivity.

Description

technical field [0001] The disclosure relates to a polyheterocyclic compound, a preparation method and its application in detecting cysteine. Background technique [0002] The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art. [0003] Cysteine ​​(Cys) is a sulfhydryl-containing amino acid that plays a very important role in many biological activities, such as metal cofactor binders in biological enzymes, protein structure stabilizers, and biological detoxifiers. In addition, cysteine ​​itself, as one of the twenty basic amino acids, participates in protein synthesis and cell growth. Cysteine ​​deficiency is also associated with many human epidemic diseases, such as cysteine ​​deficiency can lead to slow growth, hair loss, edema, lethargy, skin damage, liver damage, muscle and fat loss, and significant weight loss in children. Skeletal muscle also malfunctions; excess levels of cysteine ​​...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/62C09K11/06G01N21/64
CPCC07D277/62C09K11/06C09K2211/1037G01N21/6428G01N21/6486
Inventor 李敏勇陈新新
Owner SHANDONG UNIV
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