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Preparation method of racemic beta-aryl-gamma-butyrolactone compound

A compound, butyrolactone technology, applied in organic chemistry and other directions, can solve problems such as inability to act on static leukemia stem cells

Active Publication Date: 2020-07-10
INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the progression of acute myeloid leukemia has been delayed to some extent by a variety of treatments and bone marrow transplantation, commonly used drugs such as cytarabine can only act on the active cell cycle and not on quiescent leukemia stem cells

Method used

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  • Preparation method of racemic beta-aryl-gamma-butyrolactone compound
  • Preparation method of racemic beta-aryl-gamma-butyrolactone compound
  • Preparation method of racemic beta-aryl-gamma-butyrolactone compound

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Experimental program
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Embodiment Construction

[0026] 1. Preparation of compound 3aa

[0027]

[0028] Take 1a (1.0mmol, 184.2mg, 1.0eq.), 2a (2.0mmol, 280.1mg, 2.0eq.), catalyst (0.033mmol, 11.7mg, 0.033eq.), toluene (2.0mL), water (4.0mL ), base (5.0mmol, 506.0mg, 5eq.) under nitrogen protection, and stirred at room temperature for 24 hours. After the reaction, a small amount of saturated ammonium chloride was added, extracted three times with ethyl acetate, and the ester layer was dried by adding anhydrous sodium sulfate for 0.5 hours, filtered with suction, the solution was concentrated, purified by silica gel column chromatography, and obtained by ethyl acetate:petroleum ether= 1:8 is used as a flushing agent, and after concentration, 3aa is a colorless oily liquid. Yield: 96%. 1 H NMR (400MHz, CDCl 3 )δ7.27(dd, J=8.5,5.3Hz,2H),7.09(t,J=8.5Hz,2H),4.29–4.09(m,3H),3.97(d,J=13.0Hz,1H), 1.58(s,3H),1.25(t,J=7.1Hz,3H),1.10(s,3H). 13 C NMR (101MHz, CDCl 3 )δ169.9, 167.1, 163.8, 161.3, 129.7 (dd, J=24.2, 5.7Hz), 116....

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Abstract

The invention discloses a preparation method of a racemic beta-aryl-gamma-butyrolactone compound. According to the preparation method, an arylboronic acid compound and gamma, gamma-disubstituted furanone are subjected to an organic catalytic asymmetric Michael addition reaction. According to the efficient preparation method provided by the invention, the gamma-butyrolactone compound reacts with aryl, and the racemic beta-aryl-gamma-butyrolactone compound with a yield as high as 98% is obtained. In addition, an intermediate is provided for preparation of a leukemia stem cell inhibitor with moreeffective activity.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical compounds, and relates to a preparation method of racemic β-aryl-γ-butyrolactone compounds. Background technique [0002] Acute myeloid leukemia is a malignant disease, and the 5-year overall survival rate of patients is only 19.8%. Therapies for acute myeloid leukemia have not progressed significantly in the past 40 years. Although the progression of acute myeloid leukemia has been delayed to some extent by a variety of treatments and bone marrow transplantation, commonly used drugs such as cytarabine can only act on the active cell cycle and not on quiescent leukemia stem cells. Leukemic stem cells are the root of leukemia relapse, which have similar properties to normal stem cells, capable of unlimited proliferation and self-renewal, and can resist the therapeutic effects of chemical drugs when they are in the quiescent phase, resulting in relapse and refractory leukemia. Therefore,...

Claims

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Application Information

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IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor 刘爱芹白著双刘文倩孙帆李好佳许士琪张书铭陈泳怡
Owner INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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