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6-(5-pyridyl)-1,2,4-triazolopyridine compound, and preparation method and application thereof

A technology based on azolopyridine and pyridyl, which is applied in the field of anti-tumor compounds, can solve the problems of poor solubility, high production cost, and difficulty in the synthesis of imidazopyridazine derivatives, and achieves the advantages of easy synthesis method and easy-to-obtain synthetic raw materials Effect

Inactive Publication Date: 2013-02-13
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of imidazopyridazine derivatives is difficult, the production cost is high, and the solubility is not good

Method used

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  • 6-(5-pyridyl)-1,2,4-triazolopyridine compound, and preparation method and application thereof
  • 6-(5-pyridyl)-1,2,4-triazolopyridine compound, and preparation method and application thereof
  • 6-(5-pyridyl)-1,2,4-triazolopyridine compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 2-Acetamido-6-[2-chloro-3-(4-fluorobenzenesulfonylamino)-5-pyridyl]-1,2,4-triazol[1,5-α]pyridine (1) Preparation

[0048] Intermediate A: Preparation of 2-chloro-3-(4-fluorobenzenesulfonylamino)-5-bromopyridine (1A)

[0049] Reference J. Med. Chem. 2011, 54, 4735–4751 Synthesis.

[0050] Intermediate B: Preparation of 2-acetyl-6-[1,2,4-triazol[1,5-α]pyridinyl]boronic acid pinacol ester (1B).

[0051] Synthesized by reference WO 2009068482A1.

[0052] Synthesis of Compound 1:

[0053] Add 2-chloro-3-(4-fluorobenzenesulfonylamino)-5-bromopyridine (0.19g), 2-acetyl-6-[1,2,4-triazole[1 ,5-α]pyridyl]boronic acid pinacol ester (0.16g), PdCl 2 (pddf) (25mg), sodium carbonate (0.08g), ethylene glycol dimethyl ether (7.0mL), water (2.0mL), ethanol (3.0mL), the mixture was stirred and refluxed for 1h under nitrogen protection, and evaporated under reduced pressure The solvent and the residue were separated by silica gel column chromatography (chloroform: methanol ...

Embodiment 2

[0054] Example 2 2-Acetamido-6-[2-chloro-3-(4-methylbenzenesulfonylamino)-5-pyridyl]-1,2,4-triazol[1,5-α] Preparation of pyridine (2)

[0055] Reference J.Med.Chem.2011, 54, 4735-4751 Synthesis of 2-chloro-3-(4-methylbenzenesulfonylamino)-5-bromopyridine.

[0056] Replace 2-chloro-3-(4-fluorobenzenesulfonylamino)-5-bromopyridine with 2-chloro-3-(4-methylbenzenesulfonylamino)-5-bromopyridine, and the others are the same as in Example 1 Synthesis of compound 1. Yield 57.4%. 1 H-NMR: δ10.89(s,1H,NH),10.39(s,1H,NH),9.34(s,1H,Ar-H),8.68(s,1H,Ar-H),8.10(s, 1H,Ar-H),7.91(d,J=9.2Hz,1H,Ar-H),7.82(d,J=9.2Hz,1H,Ar-H),7.65(d,J=8.0Hz,2H, Ar-H)7.38(d,J=7.6Hz,2H,Ar-H),2.39(s,3H,CH 3 ),2.16(s,3H,CH 3 ).

Embodiment 3

[0057] Example 3 2-Acetamido-6-[2-methoxy-3-(4-fluorobenzenesulfonylamino)-5-pyridyl]-1,2,4-triazol[1,5-α] Preparation of pyridine (3)

[0058] Reference WO 2008157191A2 Synthesis of 2-methoxy-3-(4-fluorobenzenesulfonylamino)-5-bromopyridine.

[0059] Replace 2-chloro-3-(4-fluorobenzenesulfonylamino)-5-bromopyridine with 2-methoxy-3-(4-fluorobenzenesulfonylamino)-5-bromopyridine, and the others are the same as in Example 1 Synthesis of compound 1. Yield 70.4%. 1 H-NMR: δ10.84(s,1H,NH),10.08(s,1H,NH),9.23(s,1H,Ar-H),8.40(s,1H,Ar-H),8.00(s, 1H,Ar-H),7.90(d,J=9.2Hz,1H,Ar-H),7.81(m,3H,Ar-H),7.41(m,2H,Ar-H),3.64(s,3H ,OCH 3 ),2.16(s,3H,CH 3 ).

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Abstract

The invention discloses a 6-(5-pyridyl)-1,2,4-triazolopyridine compound, and a preparation method and application thereof. The medical compound is novel in structure, and the synthesis method is easy to realize. The compound has obvious antineoplastic activity and can be used for antineoplastic preparation. Determination of antineoplastic activity on cell proliferation indicates that the synthesized compound has obvious inhibiting action on the proliferation of human colon cancer cells HCT116 and human brain glioma cells U87.

Description

technical field [0001] The invention belongs to the technical field of antitumor compounds, and relates to 6-(5-pyridyl)-1,2,4-triazolopyridine compounds, their preparation method and application. Background technique [0002] Tumor is one of the malignant diseases that seriously threaten human health. In the past 20 years, the incidence and mortality of malignant tumors in my country have been increasing. The incidence of tumors is about 2 million per 100,000 people, with more than 2.2 million new cases each year, more than 1.6 million deaths, and more than 6 million patients under treatment. . [0003] At present, the treatment methods for tumors are still traditional surgery, radiation therapy and drug therapy, but to a large extent, drug therapy is still the main method. Therefore, it is of great significance to research and develop new antitumor drugs. [0004] In recent years, with the progress of tumor molecular biology research, more understanding of tumor pathogen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/444A61P35/00
Inventor 张三奇王晓朦梅其炳杨广德吕社民邵藤陈建刚
Owner XI AN JIAOTONG UNIV
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