Pyrazolopyrimidine piperazinone compounds as well as preparation method and application thereof

A compound, pyrazolo technology, applied in the field of organic compound synthesis and pharmaceutical application, can solve the problem of weak inhibitory activity of Akt1 kinase

Pending Publication Date: 2020-09-11
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, the inventors found that the Akt1 kinase inhibitors reported i...

Method used

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  • Pyrazolopyrimidine piperazinone compounds as well as preparation method and application thereof
  • Pyrazolopyrimidine piperazinone compounds as well as preparation method and application thereof
  • Pyrazolopyrimidine piperazinone compounds as well as preparation method and application thereof

Examples

Experimental program
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Embodiment

[0103] 1) Preparation of intermediate 2

[0104] 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine (1) (6.47mmol) was placed in a 100ml reaction flask, 20ml of DMF solution was added, and magnetically stirred until dissolved. Stir at room temperature and add NBS (6.79mmol), react at room temperature for 24h, TLC detects that the reaction is complete, pour the reaction solution into 200ml of ice water to quench, and gradually precipitate a white solid under stirring. After suction filtration, the filter cake was washed with water, filtered and dried to obtain Intermediate 2 as a white solid with a yield of 98.7%. Mp: 276-280°C. 1 H NMR (400MHz, DMSO-d 6 )δ(ppm):14.86(s,1H),8.86(s,1H).MS(ESI)m / z:233[M+H] + .

[0105] 2) Preparation of intermediate 3

[0106] Intermediate 2 (4.28mmol) and 1-Boc-piperazine (6.43mmol) were placed in a 250ml reaction flask, 20ml of dioxane solution was added, and magnetically stirred until dissolved. Add DIEA (8.57mmol) dropwise at room temperature, react...

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Abstract

The invention provides a pyrazolopyrimidine piperazinone compound as well as a preparation method and application thereof, and belongs to the field of organic compound synthesis and medical application. The structural formula of the pyrazolopyrimidine piperazinone compound is shown in the specification. Tests prove that the pyrazolopyrimidine piperazinone compound provided by the invention has strong inhibitory activity on Akt1 kinase, has anti-proliferative activity on mantle cell lymphoma (MCL) and has good practical application value.

Description

technical field [0001] The invention relates to the fields of organic compound synthesis and medical application, in particular to pyrazolopyrimidine piperazinone compounds and their preparation methods and applications. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Phosphatidylinositol 3-kinase (phosphatidylinositol 3-kinase, PI3K) / protein kinase B (protein kinase B, PKB, also known as Akt) signaling pathway plays an important role in regulating cell growth, proliferation, autophagy and apoptosis . Overactivation of this pathway is often observed in various tumor cells such as lymphoma, prostate cancer, myeloma, ovarian cancer, endometrial cancer, liver cancer, lung c...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/519A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07D487/04Y02P20/55
Inventor 赵桂森李玉霞郑静郭凯文禚慧君段晓明
Owner SHANDONG UNIV
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