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Preparation method of chiral gamma-butyrolactone compounds and derivatives thereof and application thereof

A butyrolactone and compound technology, applied in the field of preparation of chiral γ-butyrolactone compounds and their derivatives, can solve problems such as compound configuration changes

Pending Publication Date: 2020-06-05
INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, there is currently no report that asymmetric Michael addition of aldehydes and 2(5H)-furanone can be used to synthesize chiral γ-butyrolactone, which is a simple, fast and effective method for constructing multiple chiral centers, and chiral γ-butyrolactone compounds have strict requirements on environmental conditions and are easy to undergo racemization, thereby changing the configuration of the compound

Method used

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  • Preparation method of chiral gamma-butyrolactone compounds and derivatives thereof and application thereof
  • Preparation method of chiral gamma-butyrolactone compounds and derivatives thereof and application thereof
  • Preparation method of chiral gamma-butyrolactone compounds and derivatives thereof and application thereof

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[0049] 1. Preparation of compound 3aa

[0050]

[0051] Take 1a (1.0mmol, 36.8mg, 1.0eq.), catalyst (0.2mmol, 26mg, 0.2eq.), toluene (2.0mL), 2a (2.0mmol, 28.8mg, 2.0eq.), nitrogen protection, room temperature The reaction was stirred for 24 hours. After the reaction, add a small amount of saturated ammonium chloride, extract 3 times with ethyl acetate, add anhydrous sodium sulfate to the ester layer and dry it for 0.5 hours, filter with suction, spin dry, go through silica gel column chromatography, and use ethyl acetate:petroleum ether =1:4 as a flushing agent, separated and purified, spin-dried, added 2.0mL of dichloromethane, and added p-toluenesulfonylhydrazide (1.5mmol, 1.5eq.) under the condition of stirring below 0°C, and added enough Measure anhydrous magnesium sulfate, stir, react at room temperature for 24 hours, filter with suction, spin dry, go through silica gel column chromatography, use ethyl acetate: petroleum ether = 1:2 as eluent, separate and purify, an...

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Abstract

The invention discloses a chiral gamma-butyrolactone compound and a preparation method and an application of a derivative of the chiral gamma-butyrolactone compound. According to the preparation method, an aldehyde compound and 2-furanone are subjected to an organic catalytic asymmetric Michael addition reaction. The invention provides an effective method for combining chiral gamma-butyrolactone with three continuous chiral carbons to obtain the chiral gamma-butyrolactone compound with the yield of 89%, the dr of 9.2:1 and the ee of 99% and the derivative thereof. In addition, a cell activitytest is carried out on the chiral gamma-butyrolactone derivative obtained in the invention, so that the compound has an inhibition effect on proliferation of U251, Saos2, MGC803, 293T and Hela cell lines, and can be used as a broad-spectrum drug in treatment of various tumors.

Description

technical field [0001] The invention belongs to the field of synthesis of medical compounds, and relates to a preparation method and application of chiral γ-butyrolactone compounds and derivatives thereof. Background technique [0002] The γ-butyrolactone skeleton widely exists in various natural products and has important biological activities, such as anti-inflammation, anti-cancer and anti-virus. The Michael addition reaction based on furanone is one of the commonly used methods to construct γ-butyrolactone compounds. In recent years, asymmetric reactions catalyzed by small organic molecules have received great attention due to their advantages such as mild reaction conditions, high stereoselectivity and easy recovery. Based on this, we carried out research on the catalytic asymmetric reaction of organic small molecules to construct chiral γ-butyrolactone compounds based on furanone skeleton. Multifunctional γ-butyrolactone compounds are important intermediates in the s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33C07D307/94A61P35/00
CPCC07D307/33C07D307/94A61P35/00
Inventor 白著双朱文宁尤晓刘爱芹陈付民杜加成李佳萌田成港陈泳怡张书铭诸葛慧
Owner INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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