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Fluorenyl salicylaldehyde hydrazine derivatives, preparation method and application thereof

A technology of fluorenyl salicylaldehyde hydrazine, which is applied in the field of fluorenyl salicylaldehyde hydrazine derivatives and their preparation, can solve the problems of difference and large fluorescence shift, and achieve increased Stokes shift and electron-withdrawing ability , The effect of preventing self-absorption phenomenon

Active Publication Date: 2019-02-12
HKUST SHENZHEN RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to provide a kind of fluorenyl salicylaldehyde hydrazine derivatives and its preparation method and application, to solve the fluorescence behavior (fluorescence main peak position or luminous color) and probe in the solid state in the prior art in lipid droplets. There are obvious differences in the situation and the problem of large fluorescence shift

Method used

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  • Fluorenyl salicylaldehyde hydrazine derivatives, preparation method and application thereof
  • Fluorenyl salicylaldehyde hydrazine derivatives, preparation method and application thereof
  • Fluorenyl salicylaldehyde hydrazine derivatives, preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0065] Embodiment 1: the synthesis (FAS) of fluorenyl salicylaldehyde hydrazine

[0066]

[0067] Reflux 10g of fluorenone and 20ml of hydrazine hydrate (85%) under 100ml for 4h. After cooling, a large number of needle-like solids precipitated. After filtering, recrystallize twice with ethanol to obtain light yellow needle-packed crystals with a purity of 99% and a yield of 95%. %; take 2g of hydrazine hydrate crystals and 2ml of salicylaldehyde in 20ml of ethanol to reflux for 4h, after cooling to obtain light yellow needle-packed crystals, after filtering, wash with 75% ethanol solution to obtain the FAS structure, the yield is 99%. MALDI-TOF(m / z):[M+]calcd.C 20 h 14 N 2 O, 298.34; found, 299.34. Anal Calc. for C 20 h 14 N 2 O: C, 80.52; H, 4.73; N, 9.39; O, 5.36. Found: C, 80.62; H, 4.71; N, 9.19; O, 5.36.

Embodiment 2

[0068] Embodiment 2: Synthesis of FAS derivatives (1)

[0069]

[0070] Get 500mg of hydrazine hydrate crystals and equimolar m-hydroxysalicylaldehyde (or m-bromosalicylaldehyde) derivatives to react in 10ml of ethanol at 60°C for 4h. After cooling, light yellow crystals are obtained. After filtration, use 75% ethanol solution After cleaning, the corresponding FAS-derived structure was obtained by chromatography of the product, and the yield was >90%.

[0071] m-FAS-OH:MALDI-TOF(m / z):[M+]calcd.C 20 h 14 N 2 o 2 ,314.34; found, 315.24.AnalCalc.for C 20 h 14 N 2 o 2 H, 4.49; N, 8.91; O, 10.18. Found: C, 75.32; H, 4.48; N, 8.35; O, 10.09.

[0072] p-FAS-Br:MALDI-TOF(m / z):[M+]calcd.C 20 h 13 BrN 2 O, 377.23; found, 299.34. AnalCalc.for C 20 h 13 BrN 2 O: C, 63.68; H, 3.47; Br, 21.18; N, 7.43; O, 4.24. Found: C, 63.58; H, 3.40;

Embodiment 3

[0073] Example 3: Synthesis of FAS derivatives (2)

[0074]

[0075] Take 500mg of hydrazine hydrate crystals and equimolar N,N-diethylaminosalicylaldehyde in 10ml of ethanol and react at 60°C for 4 hours. After cooling, a red oily substance is obtained. After filtering, wash with 75% ethanol solution to obtain the product layer The corresponding FAS derivative structure was obtained by analysis with a yield of 85%.

[0076] p-FAS-N22: MALDI-TOF(m / z):[M+]calcd.C 24 h 23 N 3 O: 369.18; found, 370.66; AnalCalc.for C 24 h 23 N 3 O: C, 78.02; H, 6.27; N, 11.37; O, 4.33. Found, C, 77.93; H, 6.10; N, 11.25; O, 4.45.

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Abstract

The invention relates to the technical field of biological chemistry detection, in particular to a fluorenyl salicylaldehyde buzane derivative and a preparation method and application thereof. The compound can freely get in and out of cells and be specifically enriched at the lipid droplet positions in cells, is free of fluorescence originally and now has strong fluorescence, meanwhile, large Stokes shift is displayed under the effect of excited state intramolecular proton transfer, yellow, orange red or red fluorescence is displayed, no displacement exists basically compared with solid fluorescence outside the living body, and the probe localization position can be accurately judged, so that the cell lipid droplet, behavior and physiological process are monitored. The derivative has an extremely wide application prospect in the fields of biology, medical treatment, health and energy.

Description

technical field [0001] The invention relates to the technical field of biochemical detection, in particular to a fluorenyl salicylaldehyde hydrazine derivative and a preparation method and application thereof. 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 ot...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/88C07C249/16C07D333/32C07D209/88C07D215/233C07D219/06C07D213/65C07D213/68C07D209/36C07D239/36C07D213/53C07D209/86C12Q1/02
Inventor 唐本忠王志明赵祖金秦安军赵恩贵归晨
Owner HKUST SHENZHEN RES INST
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