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Preparation and application of sigma-2 fluorescent ligand

A kind of use and acceptor technology, applied in the field of new sigma-2 fluorescent ligand compounds, can solve the problems of low accuracy, great damage to the body, and high cost

Active Publication Date: 2022-05-13
GUANGDONG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantages of these methods are their high cost, low accuracy (high false positive, false negative), great damage to the body

Method used

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  • Preparation and application of sigma-2 fluorescent ligand
  • Preparation and application of sigma-2 fluorescent ligand
  • Preparation and application of sigma-2 fluorescent ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0037] In one aspect, the present invention provides a compound represented by structural formula I or an isomer, prodrug, pharmaceutically acceptable salt or solvate thereof.

[0038]

[0039] Among them, R 1 -R 5 independently selected from: hydrogen atom, amino group, hydroxyl group, halogen, amido group, C 1-6 Alkyl, alkylamino, alkoxy, preferably hydrogen atom, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Alkoxy; n is selected from 0, 1, 2, 3, 4, 5, preferably 1, 2, 3.

[0040] According to any of the preceding aspects, said C 1 -C 6 Alkyl is selected from methyl, methylene, ethyl, propyl, butyl, pentyl, hexyl.

[0041] According to any of the preceding aspects, said C 1 -C 6 Alkoxy is selected from methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy.

[0042] According to any of the preceding aspects, preferably, R 1 selected from: hydrogen atom, hydroxyl, methyl, methylene, ethyl, propyl, butyl, pentyl, hexyl; or R 1 Selected from: methoxy, ethoxy, propoxy, butox...

Embodiment 1

[0070] Embodiment 1: the synthesis of intermediate

[0071] 1. Synthesis of intermediate 7-methoxybenzopyran-2-oxo-3-carboxylic acid

[0072]

[0073] Take 2.0g (13.15mmol) of 2-hydroxy-4-methoxybenzaldehyde, 4.3g (26.3mmol) of diethyl malonate, 0.57g (6.56mmol) of anhydrous piperazine in a 50ml flask, add 15ml of ethanol , added to reflux, dropwise added 5 drops of glacial acetic acid (0.1mL), refluxed for 4h, cooled to room temperature, spin-dried the reaction solution, added 10% potassium hydroxide solution (100mL, 178.3mmol) and refluxed for 1.5 hours, and the solid was precipitated by suction filtration , dried, and the solid was recrystallized from ethyl acetate and methanol to obtain 1.81 g of the product, with a yield of 63.2%.

[0074] 1 H NMR (CDCl 3 ,ppm)δ12.24(b,1H),8.87(s,1H),7.65(d,1H),7.03(dd,2.4Hz,1H),6.94(d,1H),3.97(s,3H); 13 C NMR (CDCl 3 , ppm) δ166.3, 164.6, 163.1, 157.1, 151.3, 131.7, 115.2, 112.3, 110.9, 100.8, 56.3.

[0075] 2. Synthesis of inte...

Embodiment 2

[0086] Example 2: N-(2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline)ethyl)-7-methoxy-2-oxo-benzopyridine Synthesis of furan-3-carboxamide (SF-1)

[0087]

[0088] Take 0.17g (0.77mmol) of 7-methoxy-2-oxo-chromene-3-carboxylic acid, dissolve it in 10ml of thionyl chloride, reflux for 6 hours, spin dry thionyl chloride under reduced pressure, and obtain yellow solid. Dissolve 0.17g (0.72mmol) of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-ethylamine in 20ml of DCM, add 0.36g (3.6mmol) of triethylamine , ice-bathed to 0°C, and the DCM solution of the above-mentioned acid chloride was slowly added, and after the dropwise addition was completed, the temperature was raised to room temperature to react overnight. TLC monitored the completion of the reaction and added 50ml of water, extracted with dichloromethane (3×50ml), collected the organic phase, dried over anhydrous sodium sulfate to give 0.34g of a yellow solid, and recrystallized with methanol to give 0.19g of a yello...

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Abstract

The invention mainly relates to the synthesis of a series of sigma-2 fluorescent ligands and their application in the fields of pharmacy and medicine. Specifically, the present invention relates to a series of compounds containing benzopyran structure and having high affinity activity and selectivity for sigma-2 receptor. These compounds have good affinity activity for sigma-2 receptors, and have diagnostic and therapeutic effects on tumor cells highly expressing sigma-2 receptors, brain cells of Alzheimer's disease patients, and the like.

Description

technical field [0001] The present invention relates to the diagnosis or treatment of tumors, Alzheimer's disease, etc., and particularly relates to a new sigma-2 fluorescent ligand compound, its preparation method and its application in the fields of pharmacy and medicine. Background technique [0002] The sigma-2 receptor is highly expressed in tumor cells, and its density in amplified tumor cells is more than 10 times higher than that in normal cells (Br J Cancer 2000,82,1223-1232; British JCancer 1999,81,925- 933). Therefore, the sigma-2 receptor is considered as a biomarker for tumor cell expansion. Selective sigma-2 ligand compounds can be used as probes (such as fluorescent labels, radioactive labels, etc.) to diagnose the state of the tumor, that is, malignant or benign (Med Res Rev 2014, 34(3), 532–566, 2014; Biochimica et Biophysica Acta 2015, 1848, 2703–2714). [0003] β-amyloidβ-protein (Aβ) has a molecular weight of about 4kDa, is hydrolyzed from β-amyloid pr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C09K11/06A61K31/4725A61K49/00A61P25/28
CPCC07D405/12C09K11/06A61K49/0039A61P25/28C09K2211/1029C09K2211/1088
Inventor 黄云生徐道华谢晓阳李玉运马文辉陈爱芳
Owner GUANGDONG MEDICAL UNIV
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