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Kdm5b inhibitor and preparation method thereof

A KDM5B and inhibitor technology, applied in the field of KDM5B inhibitor and its preparation, can solve the problems of unclear mechanism of action, obvious off-target effect, poor PD/PK properties, etc., and achieve the effect of feasible synthesis method and high yield

Active Publication Date: 2020-04-17
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although KDM5A / B inhibitors with different structural skeleton types have been reported, there are no small molecule inhibitors due to poor selectivity, unclear mechanism of action, obvious off-target effects, lack of intracellular activity or poor PD / PK properties. clinical development stage

Method used

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  • Kdm5b inhibitor and preparation method thereof
  • Kdm5b inhibitor and preparation method thereof
  • Kdm5b inhibitor and preparation method thereof

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Embodiment Construction

[0013] The technical solutions of the present invention will be described in further detail below through specific implementation methods.

[0014] The embodiment of the present invention provides a KDM5B inhibitor, the chemical name is 4,5,6,7-tetrahydro-8H-cyclopentadiene[d][1,2,4]triazolo[1,5- a] pyrimidin-8-one, the structural formula is The preparation route of this compound is as follows:

[0015]

[0016] Add 1g (about 11.89mmoL) of 3-amino-4-hydrogen-1,2,4-triazole to the reaction flask, then add 20mL of glacial acetic acid, then slowly add 2.22mL (about 17.84mmoL) of 2-oxo Methyl cyclopentanecarboxylate was heated to reflux at 120°C, and the reaction was monitored by TLC. After the reaction was completed, the reaction system was put into ice water, a large amount of white solids were precipitated, and the white solids were directly obtained by suction filtration. After the white solid was washed with acetone, it was dried in an oven at 60°C for 6 hours to obtai...

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Abstract

The invention provides a KDM5B inhibitor, which has a chemical name of 4, 5, 6, 7-tetrahydro-8H-cyclopenta[d][1, 2, 4]triazolo[1, 5-a]pyrimidine-8-one and a structural formula shown as the specification. The invention also provides a preparation method of the above KDM5B inhibitor. The method includes: reacting 3-amino-4-hydrogen-1, 2, 4-triazole with methyl 2-oxocyclopentanecarboxylate in an acidic solvent at 115DEG C-125DEG C to synthesize the KDM5B inhibitor. The KDM5B inhibitor has the group structural unit of pyrimido1, 2, 4-triazole, and a series of KDM5B targeted compounds with antitumor activity can be prepared based on the pyrimido1, 2, 4-triazole basic skeleton. In addition, the synthesis method of the KDM5B inhibitor is feasible and has high yield.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a KDM5B inhibitor and a preparation method thereof. Background technique [0002] Cancer is a disease that seriously threatens human health and life. According to the global cancer statistics released by the World Health Organization, there were about 14.1 million new cancer cases and 8.2 million deaths in the world in 2012, of which lung cancer is the most common and deadly in the world. highest cancer. Lung cancer is a serious threat to human health. Due to the influence of external factors such as population aging, smoking and environmental pollution, the incidence and mortality of lung cancer are much higher than other cancers. As an important class of histone demethylases, KDM5B is highly expressed in tissues of lung cancer patients, and is closely related to the proliferation, invasion and metastasis, poor prognosis and multi-drug resistance of lung cancer. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61P35/00
CPCA61P35/00C07D487/04
Inventor 刘宏民余斌王帅
Owner ZHENGZHOU UNIV