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Novel pyruvate kinase M2 activator and its synthetic method

A technology of pyruvate kinase and synthesis method, which is applied in the field of new pyruvate kinase M2 activator and its synthesis, can solve problems such as complex process, and achieve the effect of reducing synthesis cost

Inactive Publication Date: 2015-02-25
SUZHOU VIVOTIDE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Technical problem to be solved: In the synthesis method of pyruvate kinase M2 activator reported in the literature, the process is relatively complicated, and the purification generally adopts the method of passing through the silica gel column, and even the high-efficiency preparation of the liquid phase is required to achieve the purpose of purifying the product

Method used

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  • Novel pyruvate kinase M2 activator and its synthetic method

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Embodiment 1

[0030] Step 1) Sodium (2.76 g, 120 mmol) was added portionwise to anhydrous EtOH (120 mL). After the sodium was completely dissolved, the solution was cooled to -10°C in an ice-salt bath, and 5-bromo-2-formylthiophene (5.73 g, 30 mmol) and ethyl azidoacetate (10.1 g, 60 mmol mol) mixture, added dropwise to the reaction system within 30 minutes. Stir at this temperature for one hour, then react at 0°C for one hour, remove the ice bath, and stir the reaction mixture at room temperature for another 30 minutes. TLC monitored the completion of the reaction. The reaction solution was added with saturated aqueous ammonium chloride solution (100 ml), and then poured into 5 times the volume of cold water, stirred, and solids were precipitated. After filtration, the solid was washed three times with water. As a light yellow solid, this solid was used directly in the next step.

[0031] Step 2) Dissolve the light yellow powder from the previous step in toluene (50 ml), dry it with an...

Embodiment 2

[0041] Step 1) Sodium (27.6 g, 1.2 mol) was added in portions to anhydrous EtOH (1.2 L). After the sodium was completely dissolved, the solution was cooled to -10°C in an ice-salt bath, and 5-bromo-2-formylthiophene (57.3 g, 300 mmol) and ethyl azidoacetate (101 g, 600 mmol mol) mixture, added dropwise to the reaction system within 30 minutes. Stir at this temperature for one hour, then react at 0°C for one hour, remove the ice bath, and stir the reaction mixture at room temperature for another 30 minutes. TLC monitored the completion of the reaction. Add saturated ammonium chloride aqueous solution (1 liter) to the reaction solution, then pour it into 5 times the volume of cold water, stir, and solid precipitates out. After filtration, the solid was washed three times with water. As a light yellow solid, this solid was used directly in the next step.

[0042] Step 2) Dissolve the light yellow powder from the previous step in toluene (500 ml), dry with anhydrous sodium sul...

Embodiment 3

[0052] Step 1) Sodium (55 g, 2.4 mol) was added portionwise to anhydrous EtOH (2.4 L). After the sodium was completely dissolved, the solution was cooled to -10°C in an ice-salt bath, and 5-bromo-2-formylthiophene (114.6 g, 600 mmol) and ethyl azidoacetate (200 g, 1.2 mole ) mixture was added dropwise to the reaction system within 30 minutes. Stir at this temperature for one hour, then react at 0°C for one hour, remove the ice bath, and stir the reaction mixture at room temperature for another 30 minutes. TLC monitored the completion of the reaction. Add saturated ammonium chloride aqueous solution (2 liters) to the reaction solution, then pour it into 5 times the volume of cold water, stir, and solid precipitates out. After filtration, the solid was washed three times with water. As a light yellow solid, this solid was used directly in the next step.

[0053] Step 2) Dissolve the light yellow solid powder in the previous step in toluene (1 liter), dry it with anhydrous so...

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Abstract

The invention relates to a synthetic method of a novel pyruvate kinase M2 activator. The structural formula of the pyruvate kinase M2 activator is shown in the specification. The method comprises the following steps: 1, condensing 5-bromo-2-formylthiophene and ethyl triazoacetate to generate a compound A; 2, refluxing the compound A in toluene to carry out loop closing in order to generate a compound B; 3, reacting the compound B with DMF and POCl3 to introduce an aldehyde group in order to generate a compound C; 4, introducing a methyl group to the compound C by using iodomethane in order to generate a compound D; 5, carrying out ring formation on the compound D under the action of hydrazine hydrate to generate a compound E; 6, condensing the compound E and 3-nitrobenzyl bromide to generate a compound F; 7, carrying out a reaction on the compound F under the action of reduced iron powder to generate a compound G; 8, reacting the compound G with sodium methyl mercaptide to generate a compound H; and 9, oxidizing the compound H by m-chloroperbenzoic acid to generate the product I.

Description

technical field [0001] The invention belongs to the technical field of biomedicine and relates to a pyruvate kinase activator and a synthesis method thereof, in particular to a novel pyruvate kinase M2 activator and a synthesis method thereof. Background technique [0002] In the 1920s, German scientist Otto Warburg discovered that the regulation of cell metabolism in rapidly growing tissues (such as embryos or tumors) is different from that of normal mature cells. Through glycolysis or the Warburg effect, cancer cells are more than other Cells absorb glucose with greater efficiency and produce energy and grow rapidly. Normal cells can only carry out glycolysis under the condition of hypoxia, while tumor cells preferentially carry out glycolysis even without hypoxia, consume more glucose and produce more lactic acid, which is the famous Warburg effect , Mr. Warburg also won the Nobel Prize in Medicine. [0003] In recent years, the field of tumor metabolism research has de...

Claims

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Application Information

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IPC IPC(8): C07D495/14A61K31/5025A61P35/00
CPCC07D495/14
Inventor 凌静刘金永王彦军
Owner SUZHOU VIVOTIDE BIOTECH
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