Pair of isomers, and preparation method and application thereof

An isomer, a pair of technology, applied in organic chemistry methods, chemical instruments and methods, analytical materials, etc., can solve problems such as peripheral system toxicity and side effects, and achieve simple post-processing methods, high yields, and fluorescent properties. stable effect

Active Publication Date: 2021-03-12
HENAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many reported compounds are not selective for the inhibition of AChE and BChE, thus causing toxic side effects on the peripheral system

Method used

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  • Pair of isomers, and preparation method and application thereof
  • Pair of isomers, and preparation method and application thereof
  • Pair of isomers, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Isomers (I) and (II), such as figure 1 As shown, its synthesis steps are as follows:

[0040] (E)-2-(2-((Z)-1,3,3-Trimethylindole-2-ethylene)ethylene)furo[2,3-b]quinoline-3, 4(2H,9H)-diketone (384 mg, 1.0 mmol) and anhydrous K 2 CO 3 (207 mg, 1.5 mmol) was added to 30 mL of anhydrous DMF, and 10 mL of a DMF solution containing diethyl sulfate (231 mg, 1.5 mmol) was added dropwise with a constant pressure dropping funnel under stirring. After the dropwise addition was completed, the temperature was raised to 60°C and the reaction was stirred for 30 minutes. After the reaction was completed, the filtrate was obtained by filtration, and the filter cake was washed three times with chloroform, 10 mL each time. The combined solutions were evaporated to dryness, 30 mL of ice water was added, and extracted three times with 30 mL of chloroform. The organic layers were combined, dried over anhydrous sodium sulfate, evaporated to dryness and purified by column chromatography....

Embodiment 2

[0045] The synthesis steps of isomers (I) and (II) of this embodiment are as follows:

[0046] (E)-2-(2-((Z)-1,3,3-Trimethylindole-2-ethylene)ethylene)furo[2,3-b]quinoline-3, 4(2H,9H)-diketone (384 mg, 1.0 mmol) and anhydrous Na 2 CO 3 (318 mg, 3.0 mmol) was added to 30 mL of acetonitrile, and 10 mL of acetonitrile solution containing diethyl sulfate (231 mg, 1.5 mmol) was added dropwise with stirring. After the dropwise addition, the temperature was raised to 70°C and stirred for 30 minutes. After the reaction was completed, the reaction solution was filtered, and the filter cake was washed three times with chloroform, 20 mL each time. Combine the filtrates, evaporate the solvent to dryness, add 30 mL of ice water, extract three times with 30 mL of chloroform, combine the organic layers, dry over anhydrous sodium sulfate, evaporate to dryness and purify by column chromatography. The eluent was petroleum ether / ethyl acetate=2:1 (volume ratio), and 196 mg of isomer (I) was o...

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Abstract

The invention discloses a pair of isomers, and a preparation method and application thereof, and the chemical structures of the pair of isomers are shown as formulas (I) and (II): the preparation method comprises the following steps: mixing (E)-2-(2-(Z)-1, 3, 3-trimethylindole-2-ethylene) ethylene) furan [2, 3-b] quinoline-3, 4 (2H, 9H)-diketone, diethyl sulfate, anhydrous potassium carbonate andan organic solvent, performing heating and reacting, concentrating an organic phase, and performing separating to obtain a product. According to the invention, two compounds are prepared by adopting aone-pot method, and the small organic molecule (I) can realize positioning and fluorescence response to lipid droplets in cells, and has the advantages of high sensitivity, rapid response, high specificity and the like; the small organic molecule (II) has fluorescence response to solution viscosity, can be used for detecting system viscosity, has strong acetylcholin esterase inhibition activity and can be used for treating related diseases.

Description

technical field [0001] The invention belongs to the fields of pharmaceutical chemical industry and biological detection. It specifically relates to a pair of isomers, their preparation method and application. Background technique [0002] The core of lipid droplets is composed of neutral fat, mainly including triglyceride and cholesteryl ester, and there is a single layer of phospholipid molecules and various protein packages outside the core. The phospholipid molecules are mainly phosphatidylcholine and phosphatidylethanolamine, followed by phosphatidylinositol. Lipid droplets interact with other organelles and may play important roles in lipid metabolism and storage, membrane transport, protein degradation, and signal transduction. In addition, studies have also shown that a variety of metabolic diseases, such as obesity, fatty liver, cardiovascular disease and diabetes, and neutral fat storage diseases are related. [0003] Commercial lipid droplet fluorescent probes, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C09K11/06G01N21/64A61P25/28
CPCA61P25/28C07B2200/09C07D491/048C09K11/06C09K2211/1029C09K2211/1033G01N21/6428
Inventor 罗稳李景华黄抗龚慧媛赵永梅
Owner HENAN UNIVERSITY
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