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Compound I and compound II based on phenanthroimidazole, and preparation method and applications thereof

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, broad application prospects, and high fluorescence quantum yield

Active Publication Date: 2017-05-10
HKUST SHENZHEN RES INST
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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 preparation method and applications thereof
  • Compound I and compound II based on phenanthroimidazole, and preparation method and applications thereof
  • Compound I and compound II based on phenanthroimidazole, and preparation method and applications thereof

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Experimental program
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Effect test

Embodiment 1

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

[0071]

[0072] React an 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 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 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. 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 (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

The invention relates to a compound I and a compound II, and a preparation method and applications thereof. According to the preparation method, different substituent group structures are introduced at the Ar sites of compounds so as to realize adjusting of emitting color and efficiency of the compounds; efficiency loss of the compounds at solid states is inhibited effectively, and high fluorescent quantum yield at water conditions is realized; different amine carboxylic acid structures are selected as reactants, different carboxylic acid structures are introduced at N1 benzene ring sites, and different carboxylic acid derivative structures are prepared via appropriate methods so as to improve molecular compatibility and identification capability of the compound structures; the compound I and the compound II are taken as novel probe structures, phenanthroimidazole carboxylic acid and carboxylic acid derivatives are capable of entering and exiting cells freely, selective identification and imaging on specific structures are carried out, and application prospect in the fields of biology, medical treatment, and monitoring is promising.

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 Applications(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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