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Compound i and compound ii based on phenanthroimidazole and their preparation method and application

A compound, naphthyl technology, applied in the field of analysis and detection, can solve problems such as the inability to realize the application of fluorescent probes, and achieve the effects of improving molecular compatibility, high fluorescence quantum yield, and broad application prospects

Active Publication Date: 2019-10-22
HKUST SHENZHEN RES INST
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  • Description
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Problems solved by technology

[0006] The object of the present invention is to provide the general structural formula as the compound of formula I and formula II and its preparation method and application, i.e. compound I and compound II and its preparation method and application, specifically to provide a class of carboxyl substituted based on phenanthroimidazole N1 Acid and carboxylic acid derivatives solve the problem that phenanthroimidazole compounds in the prior art cannot be used as fluorescent probes

Method used

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  • Compound i and compound ii based on phenanthroimidazole and their preparation method and application
  • Compound i and compound ii based on phenanthroimidazole and their preparation method and application
  • Compound i and compound ii based on phenanthroimidazole and their preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Embodiment 1: the synthesis of phenyl-phenanthroimidazole-N1-carboxylic acid and derivatives

[0071]

[0072] React appropriate amount of benzaldehyde, phenanthrenequinone, p-aminobenzoic acid and excess ammonium acetate in glacial acetic acid at 120°C for 3 hours, cool to room temperature, and filter to obtain carboxylic acid derivatives. Dissolve it in a mixed solvent of N,N-dimethylformamide and thionyl chloride, react at 80°C for 4 hours, and then spin off unreacted thionyl chloride. Excessive aniline was added to reflux for 4 hours, and the structure of the target compound was obtained through chromatographic column separation. 1 H NMR(DMSO,500MHz):δ:10.6(s,1H),8.96(d,1H),8.90(d,1H),8.70(d,1H),8.21(d,2H),7.85(d,2H ),7.79(t,1H),7.71(t,1H),7.60-7.56(m,5H),7.40-7.37(m,7H),7.11(d,1H).MALDI-TOF(m / z): [M+]calcd.C 34 h 23 N 3 O, 489.5659; found, 490.59.

Embodiment 2

[0073] Embodiment 2: Synthesis of 1-naphthyl-phenanthroimidazole-N1-carboxylic acid and derivatives

[0074]

[0075] React an appropriate amount of 1-naphthaldehyde, phenanthrenequinone, p-aminobenzoic acid and excess ammonium acetate in glacial acetic acid at 120°C for 3 hours, cool to room temperature, and filter to obtain a carboxylic acid derivative. Dissolve it in a mixed solvent of N,N-dimethylformamide and thionyl chloride, react at 80°C for 4 hours, and then spin off unreacted thionyl chloride. Excess aniline was added to reflux for 4 hours, and the structure of the target compound was obtained through chromatographic column separation. 1 H NMR (500MHz, DMSO-d 6)δ13.27(s,1H),9.02-8.97(m,1H),8.94(d,J=8.3Hz,1H),8.67(dd,J=7.9,1.4Hz,1H), 8.02-7.93(m ,4H),7.91(dd,J=8.2,1.4Hz,1H),7.83-7.65(m,5H),7.61(ddd,J=8.4,7.0,1.4Hz,1H),7.60-7.45(m,3H ),7.41(ddd, J=8.1,6.9,1.1Hz,1H),7.14(dd,J=8.3,1.2Hz,1H).MALDI-TOF(m / z):[M+]calcd.C 38 h 25 N 3 O, 539.6246; found, 540.77.

Embodiment 3

[0076] Embodiment 3: Synthesis of 2-naphthyl-phenanthroimidazole-N1-carboxylic acid and derivatives

[0077]

[0078] React an appropriate amount of 2-naphthaldehyde, phenanthrenequinone, p-aminobenzoic acid and excess ammonium acetate in glacial acetic acid at 120°C for 3 hours, cool to room temperature, and filter to obtain a carboxylic acid derivative. Dissolve it in a mixed solvent of N,N-dimethylformamide and thionyl chloride, react at 80°C for 4 hours, and then spin off unreacted thionyl chloride. Excessive aniline was added to reflux for 4 hours, and the structure of the target compound was obtained through chromatographic column separation. 1 HNMR (500MHz, DMSO-d 6 )δ10.36(s,1H),8.98(dd,J=28.1,8.4Hz,2H),8.67(dd,J=8.0,1.4Hz,1H),8.04-7.90(m,5H),7.83-7.69 (m,7H),7.66-7.49(m,4H),7.43(ddd,J=8.2,7.0,1.1Hz,1H),7.35(t,J=7.9Hz,2H),7.18(dd,J=8.4 ,1.2Hz,1H),7.11(dd,J=8.0,6.7Hz,1H).MALDI-TOF(m / z):[M+]calcd.C 38 h 25 N 3 O, 539.6246; found, 540.45.

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Abstract

Provided are compound I and compound II, a preparation method for both, and applications thereof. By introducing different substituent structures at an Ar site, implemented is the regulation of the light emission colors and efficiency of the compounds. This effectively contains loss in efficiency of the compounds in a solid-state and implements a high fluorescent quantum yield in aqueous conditions. By selecting different amino carboxylic acid structures as reactants, different carboxylic acid structures are introduced at an N1 benzene ring site, and various carboxylic acid-derived structures are prepared by means of appropriate methods, thus increasing the molecular compatibility and recognition capability of the compound structures. With compound I and compound II serving as a category of novel probe structures, phenanthrene imidazole carboxylic acid and carboxylic acid derivatives are capable of freely entering and exiting cells and selectively recognizing and imaging with respect to certain structures, thus providing extremely broad application prospects in the fields of biology, medicine, healthcare, and monitoring.

Description

technical field [0001] The present invention relates to the technical field of analysis and detection, more specifically, relates to compound I and compound II and their preparation methods and applications. Background technique [0002] With the rapid development of the national economy and the continuous improvement of people's living standards, real-time monitoring of personal health, disease prevention and treatment have gradually become people's livelihood issues that people pay more attention to. Compared with the delay of traditional in vitro chemical testing and the harmfulness of online radiation detection, fluorescence online imaging technology has gradually entered people's field of vision with its advantages of high efficiency, greenness and strong real-time performance, and has been widely used in cellular immunology, microbiology, etc. Science, molecular biology, genetics, neurobiology, pathology, oncology, clinical laboratory science, medicine, botany and othe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/02C09K11/06
Inventor 唐本忠王志明赵祖金秦安军张晓娟于大伟
Owner HKUST SHENZHEN RES INST
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