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Benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound and use thereof

A technology of benzisoselenazole and compounds, applied in the field of chemistry, can solve problems such as blood toxicity and increased risk of hypertension

Inactive Publication Date: 2013-01-30
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] (2) Gastrointestinal toxicity
[0011] (3) Blood toxicity
[0016] (6) Cardiovascular toxicity
[0017] Wu et al pointed out that the incidence of hypertension with sunitinib was 22.5%, and the risk of hypertension increased by 3.9 times compared with placebo

Method used

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  • Benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound and use thereof
  • Benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound and use thereof
  • Benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] The preparation of embodiment 1 N-phenyl-2-oximinoacetamide

[0110]

[0111] After anhydrous sodium sulfate (35g, 246mmol) was added in batches to a solution of chloral hydrate (5g, 30.5mmol) in water (90ml) at 40°C, aniline (2.57g, 27.6mmol) and 36% concentrated hydrochloric acid (3ml , 36mmol) in water (20ml) solution, then dropwise into hydroxylamine hydrochloride (6.1g, 88.4mmol) in water (27.5ml) solution, after dropping, the temperature was raised to 85°C for 2h, cooled to 50°C, suction filtered, washed with cold water, White flocculent solid (3.53 g, 78%) dried from filter cake.

Embodiment 2

[0112] The preparation of embodiment 2 isatin

[0113]

[0114] 98% concentrated sulfuric acid (46ml) was heated to 60°C, and N-phenyl-2-oximinoacetamide (1.8g, 11mmol) was added in batches under stirring, and the addition was completed within 0.5h. After the addition, the temperature was raised to 80°C for 15min. After cooling to room temperature, it was poured into 250 g of crushed ice, stirred at room temperature for 0.5 h, filtered with suction, and washed with ice water to obtain an orange solid (1.2 g, 75%).

[0115] 1 H NMR (400MHz, DMSO-d 6 ): 6.89(d, 1H), 7.04(m, 1H), 7.48(d, 1H), 7.57(m, 1H), 11.02(s, br, 1H)

Embodiment 3

[0116] Example 3 Preparation of 1,3-dihydroindolin-2-one

[0117]

[0118] Weigh isatin (0.8g, 5.4mmol), first add 0.3g of it into 80% hydrazine hydrate (10ml), heat to reflux at 100°C, add the remaining 0.5g in batches, complete the addition within 2h, and heat up to 110°C Continue to reflux for 4h, cool to room temperature, add dropwise 36% concentrated hydrochloric acid to adjust to pH = 3, continue to stir at room temperature for 12h, a solid precipitates, suction filters, washes with water to give a brown solid (0.44g, 61%).

[0119] 1 H NMR (400MHz, DMSO-d 6 ): 3.44(s, 2H), 6.79(d, 1H), 6.90(t, 1H), 7.13(d, 1H), 7.18(d, 1H), 10.33(s, br, 1H)

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Abstract

The invention discloses a benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound and a use thereof. The invention depends on and claims the priority of a Chinese patent application 201110105248.0 submitted on April 26, 2011. Through reference, all contents of the Chinese patent application 201110105248.0 are incorporated into the invention. The benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound is shown in the general formula I. The 2-indolone compound provided by the invention has excellent antitumor activity and can be widely used for preparation of antitumor drugs.

Description

technical field [0001] The invention relates to a 2-indolinone derivative and its preparation method and application, belonging to the field of chemistry. Background technique [0002] For a long time, tumor treatment has been a worldwide problem and a challenge for medical research institutes. For a long time, the commonly used cancer chemotherapy drugs in clinical practice are mainly cytotoxic drugs. This type of anticancer drug non-specifically blocks cell division and causes cell death. While killing tumor cells, it also destroys normal human cells. Therefore, it has disadvantages such as poor selectivity, strong side effects, and easy drug resistance. In recent years, with the rapid development of tumor biology and related disciplines, people have gradually realized that the essence of cell cancer is the unlimited proliferation of cells caused by the disorder of cell signal transduction pathways. The focus of research and development is shifting from traditional cytot...

Claims

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Application Information

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IPC IPC(8): C07D293/10A61K31/41A61P35/00A61P35/02
Inventor 曾慧慧田永亮洪梦实
Owner PEKING UNIV
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