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Inhibitor of glyceraldehyde-3-phosphate dehydrogenase, preparation method and application thereof

A technology of glyceraldehyde phosphate dehydrogenase and inhibitors, applied in the field of inhibitors of glyceraldehyde phosphate dehydrogenase and its preparation, can solve the problems of twice the result with half the effort in cancer drug treatment, and achieve good anticancer activity

Active Publication Date: 2015-12-23
SUN YAT SEN UNIV CANCER CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the drug resistance of tumor cells makes cancer drug treatment often less effective

Method used

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  • Inhibitor of glyceraldehyde-3-phosphate dehydrogenase, preparation method and application thereof
  • Inhibitor of glyceraldehyde-3-phosphate dehydrogenase, preparation method and application thereof
  • Inhibitor of glyceraldehyde-3-phosphate dehydrogenase, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 compound 1, the synthesis of 3-bromo-2 oxopropionic acid phenylethyl ester

[0023]

[0024] Add concentrated sulfuric acid (87μL, 1.64mmol) to the turbid solution of magnesium sulfate (788mg, 6.55mmol) in anhydrous dichloromethane (4mL), stir at room temperature for half an hour, then add 3-bromopyruvate (410mg, 2.46mmol) and phenylethyl alcohol (0.2 mL, 1.64 mmol). The reaction was carried out at room temperature, and the progress of the reaction was monitored by TLC and 1H-NMR. After the reaction, the reaction solution was diluted with dichloromethane, filtered under reduced pressure with a funnel covered with diatomaceous earth, and the filtrate was washed with saturated brine to remove excess 3-bromopyruvate, then dried with anhydrous sodium sulfate, and finally The solvent was evaporated under reduced pressure and dried in vacuo to obtain 1 as an orange liquid with a yield of 95%. 1 HNMR (400MHz, CDCl 3 ): δ7.36-7.26(m, 5H), 4.55(t, J=7.2Hz, 2H)...

Embodiment 2

[0025] Embodiment 2, compound 2, the synthesis of 3-bromo-2 oxopropionic acid-1-phenylethyl-ester

[0026]

[0027] Using the same conditions for the synthesis of phenylethyl 3-bromo-2-oxopropionate 1, 2 was successfully prepared as a green liquid with a yield of 93%. 1 HNMR (400MHz, CDCl 3 ):δ7.41-7.32(m,5H),6.03(q,J=6.4Hz,1H),4.30(s,2H),1.68(d,J=6.8Hz,3H); 13 CNMR (100MHz, CDCl 3 ): δ184.6, 158.7, 139.8, 128.7, 128.6, 127.0, 126.3, 76.0, 30.8, 21.9; IR (KBr, cm-1): υ1733, 1390, 1274, 1163, 1053.

Embodiment 3

[0028] Embodiment 3, the synthesis of compound 3,3-bromo-2 oxopropionic acid 3-pentyl ester

[0029]

[0030] Using the same conditions for the synthesis of phenylethyl 3-bromo-2-oxopropionate 1, 3 was successfully prepared as a yellow liquid with a yield of 72%. 1 HNMR (400MHz, CDCl 3 ):δ4.97-4.91(m,1H),4.29(s,2H),1.73-1.66(m,4H),0.954-0.910(m,6H); 13 CNMR (100MHz, CDCl 3 ): δ185.1, 159.5, 80.9, 30.7, 26.3, 9.5; IR (KBr, cm-1): υ1736, 1399, 1265, 671.

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Abstract

The invention provides an inhibitor of glyceraldehyde-3-phosphate dehydrogenase, a preparation method and anticancer application thereof. According to the invention, pharmacological experiments show that the compound has strong killing effect on human colon cancer cells, human gastric cancer cells and leukemia cells, and can significantly induce the apoptosis of cancer cells. Further experiments indicate that the compound inhibits the production of ATP by inhibiting the glyceraldehyde-3-phosphate dehydrogenase (GAPDH) in cancer cell glycolysis so as to kill cancer cells.

Description

technical field [0001] The present invention relates to an inhibitor, more specifically, to an inhibitor of 3-phosphate glyceraldehyde dehydrogenase and its preparation method and application. Background technique [0002] Cancer has replaced cardiovascular disease as the disease with the largest number of deaths in the world. In recent decades, cancer drug treatment has made significant progress, and some anti-tumor drugs have been developed, which effectively prolong the survival of patients or improve the patient's quality of life. However, the drug resistance of tumor cells makes the drug treatment of cancer often less effective. The unlimited malignant proliferation ability and drug resistance of tumor cells depend on tumor stem cells with special biological characteristics in tumor tissues, and its existence has been confirmed in various tumors such as breast cancer. In most tumors, even under aerobic conditions, the activity of glycolysis is higher than that of norm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/78C07C235/74C07C231/02C07C69/716C07C67/08A61K31/22A61K31/16A61K31/165A61P35/00
Inventor 黄蓬文石军胡寓旻李敏崔庆彬
Owner SUN YAT SEN UNIV CANCER CENT