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Pyridine-2-formic acid derivate and preparation method and application thereof

A technology of derivatives and formic acid, which is applied in the field of pyridine-2-carboxylic acid derivatives and their preparation, can solve the problems that the biological activity needs to be further improved and the like

Active Publication Date: 2019-07-30
XIAMEN INST OF RARE EARTH MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the biological activity of the above drugs still needs to be further improved.

Method used

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  • Pyridine-2-formic acid derivate and preparation method and application thereof
  • Pyridine-2-formic acid derivate and preparation method and application thereof
  • Pyridine-2-formic acid derivate and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Example 1 Synthesis of intermediate 3-substituted phenyl-5-hydroxymethyl-isoxazole (II) or intermediate 3-substituted phenyl-5-aminomethyl-isoxazole (III):

[0076] Using substituted benzaldehyde as raw material, it is prepared by synthesis of oxime, 1,3-dipolar cycloaddition reaction, methylsulfonyl esterification reaction, azidation and reduction reaction (R 2 and n as above), see the following process for details:

[0077]

[0078] For the specific synthesis process of intermediate 3-substituted phenyl-5-hydroxymethyl-isoxazole (II) or intermediate 3-substituted phenyl-5-aminomethyl-isoxazole (III), see patent document CN103360382A , CN103664991A and CN103601762A, the full texts of these three applications are incorporated herein by reference.

Embodiment 2

[0079] Synthesis of pyridine-2-carboxylate derivatives (I-1) shown in embodiment 2 formula (I)

[0080] Wherein take the reaction of 5-bromo-pyridine-2-carboxylic acid and 3-(4-chlorophenyl)-5-hydroxymethyl-isoxazole as an example to illustrate:

[0081] Synthesis of [(3-(4-chlorophenyl)-isoxazol-5-yl)-methyl]-5-bromo-pyridine-2-carboxylate (YP-51)

[0082]

[0083] Add 0.202g (1mmol) of 5-bromo-pyridine-2-carboxylic acid and 0.206g (1mmol) of DCC into a 50mL round bottom flask, add 10mL of dry THF, and stir in an ice bath for 30min to dissolve 0.175g (1mmol) of 5 -Hydroxymethyl-3-(4-chlorophenyl)-isoxazole and 0.209 g (1 mmol) DMAP in 10 mL THF were slowly added dropwise to the reaction system, stirred in an ice bath for 30 min, and then naturally rose to room temperature for reaction. After the TLC detection reaction was completed, the reaction solution was concentrated in vacuo, and the residue was directly separated from the column. (石油醚) :V (乙酸乙酯) =5:1~2:1) to obtai...

Embodiment 3

[0084] Synthesis of pyridine-2-formic acid amide derivatives (I-2) shown in embodiment 3 formula (I)

[0085] Wherein take the reaction of 5-bromo-pyridine-2-carboxylic acid and 3-(4-chlorophenyl)-5-aminomethyl-isoxazole as an example to illustrate:

[0086] Synthesis of N[(3-(4-chlorophenyl)-isoxazol-5-yl)-methyl]-5-bromo-pyridine-2-carboxamide (YP-108)

[0087]

[0088]Add 0.202g (1mmol) of 5-bromo-pyridine-2-carboxylic acid, 0.206g (1mmol) of DCC and 0.135g (1 mmol) of HOBT into a 50mL round bottom flask, add 10mL of dry THF, and stir in an ice bath for 30 minutes. Add 0.174g (1 mmol) 5-aminomethyl-3-(4-chlorophenyl)-isoxazole and 0.208g (1 mmol) DMAP in 10mL THF solution slowly to the reaction system dropwise, and stir for 30min in an ice bath Then naturally rise to room temperature to react. After the completion of the TLC detection reaction, the reaction solution was concentrated in vacuo, and the residue was directly separated from the column. (石油醚) :V (乙酸乙酯) =5:...

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Abstract

The invention belongs to the field of medicinal chemistry, and particularly relates to a pyridine-2-formic acid derivative of a novel structure and a preparation method and application thereof, in particular to the pyridine-2-formic acid derivative represented by formula (I), a stereoisomer, racemate, tautomer or pharmaceutically acceptable salt of the pyridine-2-formic acid derivative, a preparation thereof of the pyridine-2-formic acid derivative and the application of the pyridine-2-formic acid derivative in preparing anti-cancer drugs.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a class of novel pyridine-2-carboxylic acid derivatives and their preparation methods and uses. Background technique [0002] Cancer has become the most important lethal disease worldwide. Cancer can occur in various organs and tissues at any age. The main types of cancer that cause death are: lung cancer, breast cancer, colorectal cancer, prostate cancer and stomach cancer. [0003] Judging from the composition of the top 10 malignant tumors in urban and rural areas in my country in recent years, the incidence of lung cancer is also the highest. For men, gastric cancer, liver cancer, colorectal cancer, and esophageal cancer are high-incidence cancers; for women, breast cancer, colorectal cancer, thyroid cancer, and gastric cancer are also high-incidence cancers. According to statistics: lung cancer has replaced liver cancer as the first lethal malignant tumor in m...

Claims

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Application Information

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IPC IPC(8): C07D413/12A61P35/00A61K31/4439
CPCA61P35/00C07D413/12
Inventor 雍建平卢灿忠
Owner XIAMEN INST OF RARE EARTH MATERIALS
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