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2-indole ketone compound, preparation and uses thereof

A technology of indolinone and compound, applied in the field of chemical synthesis and application, can solve the problem of unsatisfactory activity concentration

Inactive Publication Date: 2008-04-09
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, since these compounds are ATP competitive inhibitors of PTKs, but the ATP concentration in cells, especially tumor cells, can reach more than 5 mmol / L, the concentration of such ATP competitive inhibitors should at least reach the millimolar level to perform. However, the effective inhibitory effect is not yet satisfactory, and the active concentration is still not satisfactory; therefore, it is necessary to invent new derivatives of indolinone with better curative effect

Method used

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  • 2-indole ketone compound, preparation and uses thereof
  • 2-indole ketone compound, preparation and uses thereof
  • 2-indole ketone compound, preparation and uses thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0084] 5-Chlorosulfonyl-2-indolinone

[0085] 2g of compound 3 was added in batches to 5ml of chlorosulfonic acid under ice cooling and stirred, and the system became black and viscous. After the addition, the system was slowly warmed up to 60° C. and stirred for 2 hours. After stopping heating, cool to room temperature. The reaction solution was poured into 200 g of crushed ice and continued to stir for 2 hours. Suction filtration, washing with water to neutrality, and vacuum drying gave 2.3 g of light yellow powder (4), with a yield of about 66%. .

Embodiment 2

[0087] 5-Hydroxysulfinyl-indol-2-one

[0088] 7.2gNa 2 HPO 4 .H 2 O and 5.0gNa 2 SO 3 After it was completely dissolved in 40ml of water at 30°C, 4.6g of compound 4 was added in batches and stirred. The temperature was raised to 60° C. and stirred for 4 hours. Remove from heat and cool to room temperature. Cooled in an ice bath with 9N H 2 SO 4 Adjust the pH to 1-2, and a large amount of light yellow solid precipitates. Suction filtration and vacuum drying yielded 2.83 g of light yellow compound 5, which was purified by beating with PE, washed with methanol, and concentrated with a yield of about 72%.

Embodiment 3

[0090] 5-Carboxymethylsulfonyl-indol-2-one

[0091] Dissolve 3g of compound 5 in 20ml of water, 5.8g of chloroacetic acid in 20ml of water, and adjust the pH to 7-8 with 30% NaOH aqueous solution respectively. Mix the two, stir, heat up to 95°C, and control the reaction system with 0.5N NaOH aqueous solution The pH value is between 7-8, and the reaction takes 4 hours. Remove from heat and cool to room temperature. The pH was adjusted to 1 with 3N HCl solution, and a large amount of solids precipitated out as pale yellow. Suction filtration and drying gave 2.4 g of light yellow powder (6), which was purified by beating with PE, with a yield of about 62%. 1 HNMR (DMSO-d 6 ) (ppm): 11.2 (1H, s), 10.85 (1H, d), 7.71 (2H, t), 6.98 (1H, d), 4.33 (2H, s), 1.89 (1H, s).

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Abstract

The invention relates to a new 2-indolinone compound and a preparation method and the usage to prepare the compounds. The general formula of the new derivatives of indolinone provided by the invention is the formula above, when in preparation, the 3-position and the 5-position of 2-indolinone are respectively introduced by amide and a carboxamide methyl sulfonyl structure to get the new derivatives. The 2-indolinone compounds of the invention have good activity of inhibition of tumor cell growth.

Description

technical field [0001] The present invention relates to a new class of 2-indolinone compounds, as well as the preparation method and application of these compounds. More specifically, the present invention relates to the 3-position and 5-position of 2-indolinone respectively introduce amide and carbamoyl methyl sulfone structure to obtain a class of new derivatives, and their preparation method, and these compounds are effective in inhibiting The application in tumor cell growth belongs to the technical field of chemical synthesis and application. Background of the invention [0002] Malignant tumors are the second leading cause of death in the world, and chemotherapy is an important means of treating malignant tumors. Among them, tyrosine protein kinase inhibitor antineoplastic drugs are a new type of targeted anticancer drugs. Because they avoid the damage of traditional chemotherapy drugs to normal cells and tissues of the human body, they have the advantages of high cur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06A61K31/404A61P35/00
Inventor 吕伟肖锋罗宇汤杰
Owner EAST CHINA NORMAL UNIV
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