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Bis-benzimidazole fluorescent dye as well as preparation method and application thereof

A bibenzimidazole and fluorescent dye technology, applied in the field of biological fluorescent dyes, can solve the problems of increased post-processing difficulty, a large amount of impurities, and reduced yields, and achieve rapid labeling and detection of DNA, mild conditions, and improved sensitivity and accuracy Effect

Active Publication Date: 2022-05-24
TIANJIN QUANHECHENG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the present invention finds in the research process that if this step is used to react, the cyano group will be hydrogenated in the reductive hydrogenation process, resulting in a large amount of impurities, 2,4-diaminoaniline, which reduces the reaction efficiency on the one hand. Yield, on the other hand increased the post-processing difficulty of reaction

Method used

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  • Bis-benzimidazole fluorescent dye as well as preparation method and application thereof
  • Bis-benzimidazole fluorescent dye as well as preparation method and application thereof
  • Bis-benzimidazole fluorescent dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of compound 3

[0041] Combine 5-chloro-2-nitroaniline (2.59g, 15mmol), methylpiperazine (1.5g, 15mmol) and carbonic acid

[0042] Potassium (2.1 g, 15 mmol) was added to DMF, mixed, and refluxed until the reaction was complete. The mixture was poured into cold water, extracted with ethyl acetate, the organic layer was separated, washed with water, dried over anhydrous sodium sulfate, concentrated, and subjected to silica gel column chromatography to obtain 3 g of a pale yellow solid with a yield of 85%. 1 H NMR (500 MHz, DMSO) δ7.83 (d, 1H), 7.13 (s, 1H), 6.39 (d, 1H), 6.27 (s, 1H), 3.61 – 3.53 (t, 2H), 3.47 – 3.39 (t, 2H), 2.55 (t, 2H), 2.40 (t, 2H), 2.25 (s, 3H).

Embodiment 2

[0044] Preparation of compound 4

[0045] Compound 3 (30 g, 127 mmol) and 5% palladium on carbon (18 g) were added to anhydrous ethanol, and at room temperature, hydrogen

[0046] Hydrogenation was carried out in the solution, the catalyst was removed by filtration, and the solvent was evaporated to dryness to obtain 24.5 g of a yellow-brown precipitate with a yield of 93.5%. 1 H NMR (500 MHz, CDCl 3 ) δ = 6.26 (d, 1H), 6.02 (m, 1H), 5.78 (d, 1H), 4.22 (m, 4H), 3.69 – 3.59 (t, 2H), 3.53 – 3.43 (t, 2H), 2.66 – 2.54 (t, 2H), 2.47 –2.38 (t, 2H), 2.29 (s, 3H).

Embodiment 3

[0048] Preparation of compound 5a

[0049] 3-Nitro-4-aminobenzonitrile (4.8 g, 30 mmol) was dissolved in absolute ethanol. After cooling in the ice bath, hydrogen chloride gas was bubbled through the solution, maintaining the temperature between 0-1 ºC. The reaction mixture was stored in a refrigerator (4°C) for 4-5 days to obtain an orange-yellow precipitate, which was filtered and washed with anhydrous ether to obtain a precipitate of 7.2 g with a yield of 98%. 1 H NMR (500 MHz, DMSO) δ 7.54 (s, 1H), 7.44 (dd, 1H), 6.94 (d, 1H), 3.67 (m, 2H), 1.31 (t, 3H).

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Abstract

The invention relates to a bis-benzimidazole fluorescent dye as well as a preparation method and application thereof. Aiming at the defects of the DNA fluorescent dye in the prior art, the invention provides the fluorescent dye which is simple in structure, high in fluorescence intensity and good in membrane permeability. The fluorescent dye can be prepared through simple synthesis steps, and industrial application is facilitated.

Description

technical field [0001] The invention relates to the field of biological fluorescent dyes, in particular to a bisbenzimidazole fluorescent dye compound, a preparation method and an application thereof. The fluorescent dye can be used for DNA dyeing and DNA detection by fluorescence. Background technique [0002] Nucleic acid, divided into deoxyribonucleic acid (DNA) and ribonucleic acid [0003] Acid, RNA), is the genetic material in living organisms. Complete access to the spatiotemporal distribution of nucleic acid synthesis, transport, and processing is critical for cellular function and behavior under conditions of disease, health, and external stimuli. Therefore, great efforts have been devoted to studying nucleic acid probe imaging in living cells. At present, although oligonucleotide probe methods such as molecular beacons have been widely studied, due to the advantages of low molecular weight, good membrane permeability, and fast reaction, fluorescent staining is mo...

Claims

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Application Information

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IPC IPC(8): C07D235/18C09K11/06C09B57/00G01N21/64
CPCC07D235/18C09K11/06C09B57/00G01N21/6428G01N21/6456C09K2211/1044G01N2021/6439
Inventor 杜池敏李汝娟程友文宋艳民
Owner TIANJIN QUANHECHENG TECH