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Benzyl-1H-pyrazol and benzyl-1H-pyrrole derivative and preparation method and application thereof

A technology of pyrrole derivatives and benzyl, which is applied in the field of chemical medicine and can solve problems such as poor pharmacokinetic properties, limited research, and poor activity

Inactive Publication Date: 2016-11-23
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Most of the necrosis inhibitors reported above have poor activity and poor pharmacokinetic properties, which limits their further research

Method used

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  • Benzyl-1H-pyrazol and benzyl-1H-pyrrole derivative and preparation method and application thereof
  • Benzyl-1H-pyrazol and benzyl-1H-pyrrole derivative and preparation method and application thereof
  • Benzyl-1H-pyrazol and benzyl-1H-pyrrole derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1 Preparation of 4-chloro-3-nitro-1H-pyrazole (intermediate 2a)

[0062]

[0063] Add 3-nitro-1H-pyrazole (5mmol) and NBS (5.5mmol) to the reaction flask, add 20mL DMF (N,N-dimethylformamide), then heat to 90°C and react overnight under nitrogen protection . After the reaction was complete, most of the DMF was distilled off under reduced pressure, and a large amount of solid was precipitated after adding water, filtered, washed with 20 mL of water, and dried to obtain the target product as a light yellow solid. (yield 87%)

[0064] 1 H-NMR (400MHz, DMSO-d 6 )δ:14.32(s,1H),8.37(s,1H); MS(ESI),m / z:148.1[M+H] + . Intermediates 2b, 2c were prepared by the same method as above.

Embodiment 2

[0065] Example 2 Preparation of 4-bromo-3-nitro-1H-pyrazole (intermediate 2b)

[0066]

[0067] Using the same method as the preparation of intermediate 2a, intermediate 2b was prepared with a yield of 55%.

[0068] 1 H-NMR (400MHz, DMSO-d 6 )δ:14.38(s,1H),8.45(s,1H); m / z:192.2[M+H] + .

Embodiment 3

[0069] Example 3 Preparation of 4-iodo-3-nitro-1H-pyrazole (intermediate 2c)

[0070]

[0071] Using the same method as the preparation of intermediate 2a, intermediate 2c was prepared with a yield of 20%.

[0072] 1 H-NMR (400MHz, DMSO-d 6 )δ:14.31(s,1H),8.27(s,1H); MS(ESI),m / z:148.1[M+H] + .

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Abstract

The invention belongs to the field of chemical pharmaceuticals, and particularly relates to a benzyl-1H-pyrazol and benzyl-1H-pyrrole derivative and a preparation method and application thereof. The structure of the benzyl-1H-pyrazol and benzyl-1H-pyrrole derivative is as shown in a formula I. According to the benzyl-1H-pyrazol and benzyl-1H-pyrrole derivative, the inhibitory activity on RIP1 kinase is significant, and the effect of treating ischemic myocyte necrosis in vivo is obvious. The solubility of the derivative is good, and the curative effect and pharmacokinetic property are greatly improved compared with Nec serial compounds. Meanwhile, the benzyl-1H-pyrazol and benzyl-1H-pyrrole derivative is simple in synthesis method and suitable for large-scale production. Please see the formula I in the description.

Description

technical field [0001] The invention belongs to the field of chemistry and medicine, and specifically relates to benzyl-1H-pyrazole, benzyl-1H-pyrrole derivatives and their preparation methods and applications. Background technique [0002] Programmed cell death is a new type of cell death discovered in recent years. It is a special cell death method with traditional necrosis-like cell death morphology but with programmed cell death. It usually occurs when the apoptotic pathway is inhibited, and the programmed death cells have mixed features of apoptosis and necrosis. [0003] Receptor-interacting protein 1 (RIP1) is the cross point that determines the life and death of cells, and plays an important role in the processes of cell survival and apoptosis or programmed necrosis. The complex formed by RIP1 and another receptor-interacting protein 3 (RIP3) is the key to programmed necrosis, and RIP1 is a key regulator in the process of programmed necrosis. Nec-1, the first small...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/16C07D405/06C07D207/42A61K31/415A61K31/4155A61K31/496A61K31/40A61P9/10
CPCC07D207/42C07D231/16C07D405/04C07D405/06
Inventor 杨胜勇魏于全
Owner SICHUAN UNIV
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