Amion thiazolidone compound, method for preparing same and application thereof in preparing antitumor drugs

A technology of aminothiazolidinone and compound, applied in the field of medicinal chemistry, can solve the problem that there is still no effective inhibition of Plk1

Active Publication Date: 2012-07-18
XIANGBEI WELMAN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far there is no drug that effectively inhibits Plk1

Method used

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  • Amion thiazolidone compound, method for preparing same and application thereof in preparing antitumor drugs
  • Amion thiazolidone compound, method for preparing same and application thereof in preparing antitumor drugs
  • Amion thiazolidone compound, method for preparing same and application thereof in preparing antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] The preparation of embodiment 1 intermediate 2-amino-5-(3-pyridine methylene)-4(5H)-thiazolone

[0063] To a suspension of 13.4 g (125 mmol) of 3-pyridinecarbaldehyde and 9.67 g (83.36 mmol) of thiazolamine in 60 mL of acetic acid was added 5.2 g (58.4 mmol) of alanine at room temperature. The suspension was heated at 100°C for 4 hours. Then the suspended solid was filtered and the filter cake was washed with a small amount of acetic acid and then washed with water, and dried in vacuum (40°C, 10mmHg) to obtain white 2-amino-5-(3-pyridylmethylene)-4(5H)- Thiazolone solid (16 g, yield: 62.5%).

Embodiment 2

[0064] Example 2 The preparation method of the intermediate 2-amino-5-(3-(5-fluoropyridyl)methylene)-4(5H)-thiazolone is the same as that of Example 1. 3-(5-Fluoropyridine)carbaldehyde was used as starting material.

Embodiment 3

[0065] Example 3 The preparation method of the intermediate 2-amino-5-(3-(2,4-dimethoxypyridine)methylene)-4(5H)-thiazolone is the same as that of Example 1. 3-(2,4-dimethoxypyridine)carbaldehyde was used as starting material.

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Abstract

The invention provides an amion thiazolidone compound, as shown in a formula I, wherein A1 is aryl or ceteroary; A2 is benzene ring or substituted benzene ring, double benzene nucleus or substituted double benzene nucleus, pyridine ring (including 2-, 3-, 4-pyridine) or substituted pyridine ring; and R1, R2, R3, R4, R5 and R6 are respectively H, halogen, hydroxy, cyan, amino or nitro or C1-C6 alkyl or C1-C6 alkoxy and the like; and R7 and R8 are respectively H, C1-C6 alkyl or C3-C6 naphthene base. The compound in the formula I comprises hydrate of the compound, solvate, stereoisomer, N-oxide, salt and crystalline forms which exist in various forms. Bioactivity tests show that: the compound in the formula I can restrain the activities of polo-like kinase 1 (PLK1) inside and outside the human body, and can be used for preparing antitumor drugs. The invention further provides a method for preparing the compound in the formula I.

Description

technical field [0001] The invention relates to medicinal chemistry, in particular to an aminothiazolidinone compound, its preparation method and its application in the preparation of antitumor drugs. Background technique [0002] Polo-like kinase (Plk) belongs to the family of serine-threonine kinases, which exist in various eukaryotes from yeast to mammals. Polo-like kinases in mammals include four proteins, Plk1, Plk2, Plk3 and Plk4, among which Plk1 protein performs most of the functions of Polo, Cdc5 and Plo3 (Barr, Sillje et al 2004 Nat.Rev.Mol.Cell Beol. 5, 429-440). The human Plk1 gene was first cloned and reported by Golsteyn et al. in 1994. It is located at 16p12, the mRNA is about 2.3kb long, and the molecular weight of the encoded protein is about 68kD. Extensive research in the past 10 years has shown that Plk1 is overexpressed in many malignant tumors, and it is related to the occurrence, biological behavior and prognosis of tumors. The role of Plk1 in promo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C07D277/40C07D277/54C07D407/06C07D417/14A61K31/4439A61K31/426A61K31/63A61P35/00
Inventor 孙明杰陈春麟王霆李伟孙天宇
Owner XIANGBEI WELMAN PHARMA CO LTD
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