Synthetic method for quinazolinone FPR2 formyl peptide receptor agonist

A formyl peptide receptor and quinazolinone technology, which is applied in the field of synthesis of quinazolinone FPR2 formyl peptide receptor agonists, can solve the problems of complicated preparation steps, achieve simplified preparation process, and mild reaction conditions , solvent non-toxic effect

Active Publication Date: 2016-03-09
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to provide a synthetic method of quinazolinone FPR2 formyl peptide receptor agonist, which solves the problem of complex preparation steps in the existing preparation methods

Method used

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  • Synthetic method for quinazolinone FPR2 formyl peptide receptor agonist
  • Synthetic method for quinazolinone FPR2 formyl peptide receptor agonist
  • Synthetic method for quinazolinone FPR2 formyl peptide receptor agonist

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Effect test

Embodiment 1

[0040] Weigh isatoic anhydride, aromatic hydrazide compounds, and aromatic aldehyde compounds as raw materials according to the ratio of the amount of substances 1:1:1; mix the weighed raw materials in ethanol, use nano-copper oxide as a catalyst, and add catalyst The ratio of the amount of the isatoic anhydride to the amount of the substance of isatoic anhydride is 1:0.02, and a one-pot synthesis reaction is carried out, the reaction temperature is 60 ° C, and the reaction time is 6 hours; the reactant after the reaction is separated and purified by column chromatography. A quinazolinone FPR2 formyl peptide receptor agonist is prepared.

Embodiment 2

[0042] Weigh isatoic anhydride, aromatic hydrazide compounds, and aromatic aldehyde compounds as raw materials according to the ratio of the amount of substances 1:1:1; mix the weighed raw materials in ethanol, use nano-cerium oxide as a catalyst, and add catalyst The ratio of the amount to the amount of isatoic anhydride is 1:0.05, and the one-pot synthesis reaction is carried out, the reaction temperature is 70 ° C, and the reaction time is 8 hours; the reactant after the reaction is separated and purified by column chromatography. A quinazolinone FPR2 formyl peptide receptor agonist is prepared.

Embodiment 3

[0044] Weigh isatoic anhydride, aromatic hydrazide compounds, and aromatic aldehyde compounds as raw materials according to the ratio of the amount of substances 1:1:1; mix the weighed raw materials in ethanol, and use nanometer iron tetroxide as a catalyst, The ratio of the amount of catalyst added to the amount of isatoic anhydride is 1:0.08, a one-pot synthesis reaction is carried out, the reaction temperature is 90 ° C, and the reaction time is 10 h; the reactants after the reaction are separated by column chromatography Purify to obtain quinazolinone FPR2 formyl peptide receptor agonist.

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Abstract

The invention discloses a synthetic method for a quinazolinone FPR2 formyl peptide receptor agonist. The method is specifically implemented according to the following steps of: weighing isatoic anhydride, an aromatic hydrazide compound and an aromatic aldehyde compound with the ratio of amount of substance of 1:1:1 as raw materials; after mixing the raw materials in a solvent, performing a one-pot synthetic reaction by taking a nano metal oxide as a catalyst; and separating and purifying a reaction product after the reaction by virtue of column chromatography to obtain the quinazolinone FPR2 formyl peptide receptor agonist. The synthetic method disclosed by the invention reduces the complexity of preparation by simplifying the preparation process, and moreover, the reaction condition is mild, the raw materials are low in price and are easily available, the product is high in yield, and the solvent in the preparation process is non-toxic, so that the synthetic method has a good industrial application prospect.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a synthesis method of a quinazolinone FPR2 formyl peptide receptor agonist. Background technique [0002] Quinazolinone compounds are an important nitrogen-containing heterocyclic compound. About 150 alkaloids isolated from natural products have quinazolinone ring skeletons, which exhibit good biological activities in antibacterial and anti-inflammatory. It also has good pharmacological activity in anti-hypertension, anti-tumor, and anti-HIV. The green and efficient synthesis of quinazolinone compounds with medicinal value has become a hot topic of widespread concern. QuinC1 is a non-peptide formyl peptide receptor agonist with quinazolinone as the backbone. Formyl peptide receptor agonists play a key role in the regulation of inflammatory responses and the defense of sensory cell dysfunction. , non-peptide small molecule agonists have become a better choice for clinical applicatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/92C07D401/12
CPCC07D239/92C07D401/12
Inventor 张金刘佳马养民程佩
Owner SHAANXI UNIV OF SCI & TECH
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