A kind of synthetic method of paeonol and its structural analogs

A technology similar in structure to paeonol, which is applied in the field of synthesis of natural products, can solve the problems of inability to carry out biological activity testing and evaluation, chemical synthesis method reporting, etc., and achieve the effect of simple operation and low cost

Inactive Publication Date: 2018-01-12
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And carried out preliminary biological activity test and evaluation to it, but because the amount of natural product that is separated is very limited (5 kilograms of dry Radix Paeoniae Alba root only obtains 1.6 milligrams of Radix Paeoniae Alba, can't carry out systematic biological activity test and evaluation
Up to now, there is no relevant chemical synthesis method reported at home and abroad

Method used

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  • A kind of synthetic method of paeonol and its structural analogs
  • A kind of synthetic method of paeonol and its structural analogs
  • A kind of synthetic method of paeonol and its structural analogs

Examples

Experimental program
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Effect test

Embodiment 1

[0017]

[0018] 1. Dissolve 3.2g (21mmol) of the salicylaldehyde derivative shown in formula 2-1 in 30mL of toluene and THF in a mixed solvent with a volume ratio of 1:1, cool the system to -78°C, add 3mL (90 %, 25mmol) ethyl diazoacetate, 0.4mL (50%, 0.21mmol) tetrafluoroborate ethyl ether complex, the system was slowly warmed up to room temperature, after 12 hours of reaction, the organic solvent was removed under reduced pressure, and added to the system 3mL of concentrated sulfuric acid, stirred for 1 hour, extracted with ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the organic solvent was removed under reduced pressure, and the residue was separated by silica gel column chromatography to obtain benzene represented by formula 3-1. And furyl ester, its productive rate is 90%, and structural characterization data is as follows: 1 H NMR (600MHz, acetone) δ: 8.37(s, 1H), 8.33(s, 1H), 7.49(s, 1H), 7.35(s, 1H), 4.35(q, J=7.1Hz, 2H), 2.34 (s, 3...

Embodiment 2

[0022]

[0023] 1. Take 2.0g (16.4mmol) of salicylaldehyde shown in formula 2-2 and dissolve it in 30mL of toluene and THF in a mixed solvent with a volume ratio of 1:1, cool the system to -78°C, add 2.6mL (90 %, 24.6mmol) ethyl diazoacetate, 0.3mL (50%, 0.16mmol) tetrafluoroborate ethyl ether complex, the system was slowly warmed up to room temperature, after 12 hours of reaction, the solvent was removed under reduced pressure, and the system was added 3mL of concentrated sulfuric acid, stirred for 1 hour, extracted with ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the organic solvent was removed under reduced pressure, and the residue was separated by silica gel column chromatography to obtain the benzene compound shown in formula 3-2. And furyl ester, its productive rate is 92%, and structural characterization data is as follows: 1 H NMR (600MHz, CDCl 3 )δ: 8.24 (s, 1H), 8.10-8.04 (m, 1H), 7.54-7.49 (m, 1H), 7.38-7.32 (m, 2H), 4.40 (q, J=...

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Abstract

The invention discloses a synthetic method of paeonia veitchii lynch alcohol and a structural analogue thereof. The method comprises the following steps: forming a benzofuran derivative under the catalysis of lewis acid by adopting commercially available or known salicylaldehyde or a derivative thereof and ethyl diazoacetate as raw materials, and performing intermolecular cycloaddition reaction between a reduction product of the benzofuran derivative and a salicyl alcohol compound to obtain a paeonia veichii lynch alcohol natural product or a structural analogue thereof, so that the first chemical synthesis of the paeonia veitchii lynch alcohol and the structural analogue thereof is realized. The gram-scale preparation of the natural product paeonia veitchii lynch alcohol and the structural analogue thereof can be realized only by virtue of three steps of chemical transformation in a whole synthetic route, and the synthetic route has the advantages of simplicity, high efficiency, simplicity in operation, low cost and the like and is suitable for the mass synthesis of the paeonia veitchii lynch alcohol and the structural analogue thereof, so that an important substance foundation is provided for evaluating the biological activity of the natural product paeonia veitchii lynch alcohol and the structural analogue thereof.

Description

technical field [0001] The invention belongs to the technical field of synthesis of natural products, and in particular relates to a synthesis method of paeonol and structural analogues thereof. Background technique [0002] Natural products are an important source of drug discovery and play an important role in modern drug development. According to statistics, during the period from 2008 to 2013, 100 natural products and their derivatives were approved by the US FDA or the EU EMA to enter clinical research, and 8 of them were finally approved for marketing as new drugs. Under the current background of large investment in new drug research and development, long time period, and low drug success rate, it is not difficult to find that natural products and their derivatives have an irreplaceable position in modern drug research and development. However, since the amount of natural products obtained by isolation is usually very small, scientists have not had the opportunity to ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 赵玉明徐伦王瑄徐利文
Owner SHAANXI NORMAL UNIV
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