Application of alkannin glucoside to preparation of pyruvate kinase inhibitor

A technology of pyruvate kinase and shikonin, applied in medical preparations containing active ingredients, organic active ingredients, drug combinations, etc.

Inactive Publication Date: 2012-07-11
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] So far, there is no report that shikonin glycosides have pyruvate kinase inhibitory activity

Method used

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  • Application of alkannin glucoside to preparation of pyruvate kinase inhibitor
  • Application of alkannin glucoside to preparation of pyruvate kinase inhibitor
  • Application of alkannin glucoside to preparation of pyruvate kinase inhibitor

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Embodiment Construction

[0028] The present invention is further described below in conjunction with specific embodiment, but protection scope of the present invention is not limited thereto:

[0029] Experimental Materials:

[0030] Shikonin glycosides are synthesized by themselves in the present invention, and the synthesis method is as follows:

[0031] Under the protection of nitrogen, add activated 4A molecular sieve to trichloroacetimide ester containing glycosyl or acetyl-substituted glycosyl and 1 to 2 times the mole of shikonin, and dissolve dichloro The boron trifluoride ether solution of 0.1 times the molar amount of methane was added dropwise in about 30 minutes, and the reaction was continued for 1 hour, and the reaction process was tracked by TLC. After the reaction, triethylamine was added to neutralize the boron trifluoride in the reaction solution, and then the solution was changed from dark blue to red with acetic acid, filtered, the filtrate was spin-dried, and separated by column ...

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Abstract

The invention provides an inhibitor of M2 type pyruvate kinase (PKM2)-a type of carbamic acid alkannin ester compound. Compound 3 is the currently reported M2 type pyruvate kinase inhibitor. The inhibition effect of carbamic acid alkannin ester on PKM2 is found to be higher than that of the Compound 3. Therefore, as an inhibitor of pyruvic acid, the carbamic acid alkannin ester has important application value. A type of new pyruvate kinase inhibitor-carbamic acid alkannin ester is provided, provides basis for selection of new medicaments and has important application prospect.

Description

(1) Technical field [0001] The present invention mainly relates to the application of shikonin glycoside in the preparation of pyruvate kinase inhibitors. (2) Background technology [0002] The shikonin glycoside mainly involved in the present invention is an artificially synthesized naphthoquinone compound, and the synthesis method refers to Chinese patent CN 200910152938.4. [0003] Pyruvate kinase is a key rate-limiting enzyme in glycolysis and plays a key role in energy metabolism. The M2-type pyruvate kinase (PKM2 for short) involved in the present invention mainly exists in the early development of individuals and tumor tissues. There are few PKM2 inhibitors reported so far, among which small molecule compound inhibitors are only one case of compound 3 (Vander Heiden MG, Christofk HR, Schuman E, Subtelny AO, Sharfi H, Harlow EE et al. Biochem Pharmacol2010, 79, 1118) , the amount of which inhibits 50% of the enzyme activity (ie IC50) is 50 μM. [0004] So far, there...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/7032A61P35/00
Inventor 胡汛陈晶苏叶华姜政王彦广
Owner ZHEJIANG UNIV
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