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2-pyridyl-1h-benzimidazole-4-amide derivatives

A technology of benzimidazole and amide type, which is applied in the field of 2-pyridyl-1H-benzimidazole-4-amide type derivatives, can solve the problems such as no reports on the influence of the 4-position substituent compound on the medicinal properties.

Inactive Publication Date: 2006-08-30
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although the above two articles discussed the influence of the 2-position substituent in the benzimidazole structure on the drug properties, the effect of the modification of the 4-position substituent on the drug properties of the compound has not been reported.

Method used

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  • 2-pyridyl-1h-benzimidazole-4-amide derivatives
  • 2-pyridyl-1h-benzimidazole-4-amide derivatives
  • 2-pyridyl-1h-benzimidazole-4-amide derivatives

Examples

Experimental program
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Embodiment 1

[0028] Embodiment 1 is the synthesis of basic raw material 2,3-diaminobenzoic acid. Examples 2-4 are the synthesis of intermediate 2-pyridyl-1H-benzimidazole-4-carboxylic acid. Examples 5-22 are the synthesis of the target product 2-pyridyl-1H-benzimidazole-4-amide series derivatives.

Embodiment l

[0029] Embodiment 1: the synthesis of 2,3-diaminobenzoic acid

[0030] The first step, the synthesis of 2-aminoacetyl-3-nitrobenzoic acid

[0031] Add 30g of 3-nitrophthalic anhydride in batches to 45ml of concentrated ammonia water, heat to 60°C, and keep the temperature for 2 hours. Cooling precipitated needle-like crystals. The crystals were acidified with a slight excess of hydrochloric acid to obtain a white solid, and 29.4 g of the product 2-aminoacetyl-3-nitrobenzoic acid was filtered and dried.

[0032] The second step, the synthesis of 2-amino-3-nitrobenzoic acid

[0033] 13.9 g of bromine was dropped into 100 ml of an aqueous solution of 7.3 g of sodium hydroxide at 0°C. Then 17 g of 2-aminoacetyl-3-nitrobenzoic acid were added. When heated to 80°C, a large amount of red solid precipitated out of the reaction system. After filtration, the red solid was acidified to obtain a yellow product, which was dried to obtain 13.7 g of 2-amino-3-nitrobenzoic acid. The cru...

Embodiment 2～4

[0036] Examples 2-4: Synthesis of 2-pyridyl-1H-benzimidazole-4-carboxylic acid

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Abstract

The invention provides 2-pyridyl-1H-benzimidazole-4-amide derivatives. Its chemical structural formula is showed in graph: wherein R represents respectively F, Cl, Br, CH3, OH, NO2 and H. The derivatives have good anti-virus effect and potential inhibition ability to PARP.

Description

Technical field: [0001] The present invention relates to a kind of 2-pyridyl-1H-benzimidazole-4-amide type derivatives, which have good antiviral effect (Coxsackie B3 virus). Background technique: [0002] With the improvement of people's living standards, people pay more and more attention to their health, and at the same time, the development and research of drugs for the prevention and treatment of diseases are developing faster and faster. [0003] William A.Denny of Auckland University of Pharmaceutical Sciences in New Zealand published an article in J.Med.Chem. (1990.33.814-819) and reported the preparation of a series of compounds with the following structures, and pointed out that they have good antitumor effects. [0004] [0005] R 1 represent: [0006] [0007] Roger John Griffin reported in the patent US6100283 that they synthesized a series of compounds with the following structures, and pointed out that they are good PARP [poly(ADP-ribose) polymerase] i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D235/14C07D213/58
Inventor 罗先金程俊修乃云李祥斌
Owner SHANGHAI JIAOTONG UNIV