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Furanocoumarin-Tr*ger's Base derivative as well as synthesis method and application thereof

A synthetic method and -base technology, which is applied in the field of furanocoumarin Base derivatives and their synthesis, can solve the problem of not being able to detect two metabolites at the same time, achieve good scale application prospects, high yield, and reaction The effect of mild conditions

Active Publication Date: 2019-12-10
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the methods used to detect neuroblastoma can only detect one of the metabolites, and cannot detect the presence of two metabolites at the same time.

Method used

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  • Furanocoumarin-Tr*ger's Base derivative as well as synthesis method and application thereof
  • Furanocoumarin-Tr*ger's Base derivative as well as synthesis method and application thereof
  • Furanocoumarin-Tr*ger's Base derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Furocoumarins of the present invention The synthetic route of Base derivative is as follows:

[0056]

[0057] Specifically include:

[0058] (1) Preparation of Intermediate 1

[0059]Add p-bromoaniline (60mmol) and paraformaldehyde (n=3) (150mmol) into a 250mL dry round bottom flask, cool to minus 15°C, slowly add 120mL trifluoroacetic acid dropwise through a constant pressure dropping funnel, after the drop The reaction system was moved to room temperature and reacted for 7 days, quenched with ice water, adjusted the pH to neutral with ammonia water, extracted with dichloromethane (50mL×3), and the organic phase was extracted with saturated brine, dried over anhydrous sodium sulfate, and Chromatographic separation and purification (petroleum ether: ethyl acetate = 5:1), and finally recrystallized with acetone, dried to obtain intermediate 1.

[0060] (2) Preparation of Intermediate 2

[0061] Add intermediate 1 (5mmol) to a 100mL dry round bottom flask, then a...

Embodiment 2

[0366] Embodiment 2 antitumor activity:

[0367] Compounds 6 and 7 were preliminarily tested on human triple-negative breast cancer cells (MDA-MB-231), human liver cancer cells (HepG-2), human lung cancer cells (A549) and human liver immortalized cells (THLE) by MTT method. , Cytotoxicity of human bronchial epithelial cells (HBE). The results are shown in Table 2. There are three compounds (7h, 7i, 7l) at different concentrations (μg / mL), showing different degrees of inhibition and no inhibition on human bronchial epithelial cells (HBE).

[0368] Table 2. The inhibitory rate of compound 7 on cancer cells and normal cells a (IC 50 ,μg / mL)

[0369]

[0370] a IC 50 Values ​​above 50 are marked as "-"

Embodiment 3

[0371] Example 3 Compound recognition of neuroblastoma markers homovanillic acid (HVA) and mandelic vanillic acid (VMA)

[0372] This embodiment is to test the fluorescent properties of compounds 6 and 7 to detect their recognition of neuroblastoma markers homovanillic acid (HVA) and mandelic vanillic acid (VMA). The test results are as follows: Figure 1-5 and shown in Table 3 below. Wherein, table 3 is the fluorescent property of compound 6h to HVA and VMA, figure 1 Fluorescence emission spectrum for 6h interacting with HVA and MVA, figure 2 Fluorescence emission spectra for 6h in the presence of different concentrations of HVA, image 3 is the standard curve of compound 6h to HVA, Figure 4 Fluorescence emission spectra for 6h in the presence of different concentrations of VMA, Figure 5 It is the standard curve of compound 6h to VMA. After testing, it was found that 6h has a fluorescent recognition effect on both HVA and VMA, and can be used for simultaneous qualitat...

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Abstract

The invention provides a furanocoumarin-Base derivative, wherein the structural formula of the derivative is as shown in the following formula 6 or 7; the derivative is synthesized by performing ringformation and coupling reaction on parabromoaniline,paraformaldehyde, 4-hydroxycoumarin, isonitrile and n-butyllithium; and the synthesis process is mild in reaction condition, short in reaction timeand high in yield. The Base derivative containing a coumarin fragment has excellent luminescent property and high bioactivity; some of the products have anti-tumor activity, show high-selectivity inhibition on human triple negative breast cancer cells (MDA-MB-231) and have research value of being further developed into anti-tumor medicines; and the other products can be applied to synchronous detection on neuroblastoma metabolites homovanillic acid (HVA) and vanilmandelic acid (VMA) and have the potential of being developed into a high-efficiency fluorescent probe for human neuroblastoma earlywarning and definite diagnosis.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a class of furanocoumarins Base derivatives and their synthesis methods and applications. Background technique [0002] Neuroblastoma (Neuroblastoma, NB) is the most common extracranial solid malignant tumor in children. Nearly half of neuroblastoma occurs in infants under 2 years old. The incidence of neuroblastoma in children is second only to leukemia and CNS tumors. Nervous system tumors. NB can occur anywhere in the sympathetic nervous system and adrenal medulla, and the neck, mediastinum, and abdomen are common sites. Neuroblastoma is relatively insidious in onset but develops rapidly. Most of the children had already developed distant metastases at the time of treatment, and the clinical manifestations were irregular and varied. [0003] Early detection and diagnosis of neuroblastoma is of great significance to saving more patients' lives. It has been found that hom...

Claims

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Application Information

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IPC IPC(8): C07D519/00C09K11/06A61P35/00G01N21/64
CPCC07D519/00C09K11/06A61P35/00G01N21/643C09K2211/1044C09K2211/1088
Inventor 苑睿张珑严宛瑜吴翚
Owner XUZHOU NORMAL UNIVERSITY
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