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A kind of 3,5-dibenzimidazolyl-8-p-cyanophenyl fluorine boron derivatives and its preparation method and application

A technology based on benzimidazolyl and fluorine-based fluorine, which is applied in the field of fluorine-fluorine derivatives, can solve the problems of complex structure, high price and inconvenient synthesis of endoplasmic reticulum targeting reagents, and achieve low-cost and low-cost products , low cost effect

Active Publication Date: 2020-08-11
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a small molecule of fluorine-boron derivatives that can be used for endoplasmic reticulum labeling. Using the fluorine-boron derivatives of the present invention for fluorescent labeling of endoplasmic reticulum can effectively solve the internal problems in the prior art. Plasma reticulum targeting reagents are complex in structure, inconvenient to synthesize, and expensive

Method used

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  • A kind of 3,5-dibenzimidazolyl-8-p-cyanophenyl fluorine boron derivatives and its preparation method and application
  • A kind of 3,5-dibenzimidazolyl-8-p-cyanophenyl fluorine boron derivatives and its preparation method and application
  • A kind of 3,5-dibenzimidazolyl-8-p-cyanophenyl fluorine boron derivatives and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis of 3,5-dibenzimidazolyl-8-p-cyanophenylfluoroborin

[0051] 8-p-Cyanophenylfluoroborate (14.6mg, 0.05mmol), benzimidazole (23.6mg, 0.20mmol), AgOAc (33.4mg, 4.0equiv), dimethyl sulfoxide (1.0mL) were added to the reaction tube, stirred evenly under nitrogen, heated to 80°C, and reacted for 12 hours; the specific reaction formula is as follows:

[0052]

[0053] After the reaction is complete, cool the reaction tube to room temperature, remove the solvent and add 10 mL of dichloromethane to dissolve the reaction system, then filter through diatomaceous earth and wash with 10-20 mL of dichloromethane, combine the filtrates, remove the solvent under reduced pressure, The residue was separated and purified by silica gel column chromatography (dichloromethane / petroleum ether / ethyl acetate=2:2:1, v / v / v), and after vacuum drying, the target product 3,5-dibenzimidazole was obtained as a black solid 15.7 mg of 1-8-p-cyanophenylfluoroborate, the yield was 60%.

[0...

Embodiment 2

[0057] The ultraviolet-visible-near-infrared absorption spectrum and fluorescence emission spectrum of the compound 3,5-dibenzimidazolyl-8-p-cyanophenylfluoroborate prepared in Example 1

[0058] The compound 3,5-dibenzimidazolyl-8-p-cyanophenylfluoroboron was dissolved in dichloromethane to form 1×10 - 5 mol / L, take 2.5mL and put it into a cuvette, and measure the UV-visible-near-infrared absorption and fluorescence emission spectra.

[0059] Figure 4 It is the UV-visible absorption spectrum and fluorescence emission spectrum of the compound 3,5-dibenzimidazolyl-8-p-cyanophenylfluoroborate, wherein the black solid line represents the UV-vis absorption spectrum, and the black dotted line represents the fluorescence emission spectrum. From Figure 4 It can be seen that the maximum absorption peak of the absorption spectrum of the compound 3,5-dibenzimidazolyl-8-p-cyanophenylfluoroborate is located at 561nm; the maximum absorption peak of the fluorescence emission spectrum i...

Embodiment 3

[0061] The compound 3,5-dibenzimidazolyl-8-p-cyanophenylfluoroborate prepared in Example 1 and the commercially available endoplasmic reticulum stain ER-Tracker TM Fluorescence confocal confocal imaging of Green in HepG2 cells

[0062] First, add 5% CO to the DMEM(H) medium containing 10% fetal bovine serum 2 , HepG2 cells were cultured at 37°C for 24 hours. The culture medium was removed, and 2.5 μM of the compound 3,5-dibenzimidazolyl-8-p-cyanophenylfluoroborate in phosphate buffer was added, followed by 1 μM of the commercially available endoplasmic reticulum stain ER-Tracker TM Green was co-incubated at 37°C for 30 minutes. After the culture is over, take out the culture glass-bottom dish, wash it with phosphate buffer saline for 2 to 3 times, and image the culture glass-bottom dish through a fluorescent confocal microscope.

[0063] Figure 5 It is the fluorescence imaging image of the compound 3,5-dibenzimidazolyl-8-p-cyanophenylfluoroborate (excitation wavelength:...

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Abstract

The invention provides a 3,5-dibenzimidazolyl-8-p-cyanophenyl boron-dipyrromethene derivative, and belongs to the technical field of boron-dipyrromethene derivatives. The boron-dipyrromethene derivative has the structure represented by the following formula I in the specification. The present invention also provides a preparation method of the boron-dipyrromethene derivative method. A synthetic route used in the method is a C-H / N-H direct oxidative coupling reaction, compared with a conventional ammoniation preparation method of the boron-dipyrromethene derivative, organic synthesis steps areshortened, a cumbersome process of pre-activation of a substrate is avoided, the compatibility of the reaction is increased, and the overall yield of the synthesis reaction is improved. The boron-dipyrromethene derivative is applied to cell endoplasmic reticulum specific fluorescence development and fluorescent labeling, is far lower in price than a commercially available endoplasmic reticulum labeling reagent, and can solve the problems of complicated reagent structure, inconvenient synthesis and expensive price of an endoplasmic reticulum targeting agent in the prior art.

Description

technical field [0001] The invention belongs to the technical field of borofluorene derivatives, and specifically relates to a 3,5-dibenzimidazolyl-8-p-cyanophenylfluoroborofluorine derivative and a preparation method and application thereof. Background technique [0002] The endoplasmic reticulum is a very important multifunctional organelle in eukaryotic cells. The synthesis, folding and modification of intracellular proteins, the synthesis of lipids and sterols take place in the endoplasmic reticulum. While completing these basic physiological functions, the endoplasmic reticulum has become a hub platform for coordinating signal transduction by virtue of its huge membrane structure, maintaining the stability of the intracellular environment. When genetic or environmental damage causes endoplasmic reticulum stress, excessive endoplasmic reticulum stress or prolonged endoplasmic reticulum stress can cause apoptosis, which can lead to a series of diseases [see: J.E.Vance, Tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09B57/00C09K11/06G01N21/33G01N21/64
CPCC07F5/022C09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1055G01N21/33G01N21/6428
Inventor 吴迪章华星兰静波杨宇东杨修光梁文博
Owner SICHUAN UNIV
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