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Benzyl-1H-pyrazole and benzyl-1H-pyrazole derivatives, and preparation method and application thereof

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

Active Publication Date: 2016-06-15
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-pyrazole and benzyl-1H-pyrazole derivatives, and preparation method and application thereof
  • Benzyl-1H-pyrazole and benzyl-1H-pyrazole derivatives, and preparation method and application thereof
  • Benzyl-1H-pyrazole and benzyl-1H-pyrazole derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0057] The preparation of embodiment 14-chloro-3-nitro-1H-pyrazole (intermediate 2a)

[0058]

[0059] Add 3-nitro-1H-pyrazole (5 mmol), NBS (5.5 mmol) and 20 mL of DMF (N,N-dimethylformamide) into the reaction flask, 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%)

[0060] 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 24

[0061] Preparation of Example 24-bromo-3-nitro-1H-pyrazole (intermediate 2b)

[0062]

[0063] Using the same method as the preparation of intermediate 2a, intermediate 2b was prepared with a yield of 55%.

[0064] 1 H-NMR (400MHz, DMSO-d 6 )δ:14.38(s,1H),8.45(s,1H); m / z:192.2[M+H] + .

Embodiment 34

[0065] Preparation of Example 34-iodo-3-nitro-1H-pyrazole (intermediate 2c)

[0066]

[0067] Using the same method as the preparation of intermediate 2a, intermediate 2c was prepared with a yield of 20%.

[0068] 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 medicine, and particularly relates to benzyl-1H-pyrazole and benzyl-1H-pyrazole derivatives, and a preparation method and application thereof. The structure of the benzyl-1H-pyrazole and benzyl-1H-pyrazole derivatives is disclosed as Formula I. The invention also provides a preparation method and application of the benzyl-1H-pyrazole and benzyl-1H-pyrazole derivatives. The benzyl-1H-pyrazole and benzyl-1H-pyrazole derivatives provided by the invention have obvious inhibiting activity for RIP1 kinase, and have obvious effects on in-vivo therapy of ischemic myocardial cell necrosis. The derivatives have favorable solubility, and have greatly higher properties than the Nec-series compounds in the aspects of curative effect and pharmaceutical properties. The synthesis method of the benzyl-1H-pyrazole and benzyl-1H-pyrazole derivatives is simple, and is suitable for large-scale production.

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 uses. 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 characteristics 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 process 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 mo...

Claims

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Application Information

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IPC IPC(8): C07D231/16C07D405/04C07D207/42A61K31/415A61K31/4155A61K31/496A61K31/40A61P9/10A61P25/28A61P37/00A61P35/00
CPCC07D207/42C07D231/16C07D405/04C07D405/06
Inventor 杨胜勇魏于全
Owner SICHUAN UNIV
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