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A technology of benzisoselenazole and compounds, applied in the field of chemistry, can solve problems such as increased risk of hypertension, elevated blood pressure, and blood toxicity
Inactive Publication Date: 2014-10-29
PEKING UNIV
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[0017] At the beginning of 2008, Wu et al. pointed out that all VEGF inhibitors may cause blood pressure to increase. The incidence of hypertension with sunitinib was 22.5%, and the risk of hypertension increased by 3.9 times compared with placebo.
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Embodiment 1
[0075] The preparation of embodiment 1N-phenyl-2-oximinoacetamide
[0076]
[0077] After anhydroussodiumsulfate (35g, 246mmol) was added in batches to a solution of chloralhydrate (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 hydroxylaminehydrochloride (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.
[0080] 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%).
[0082] Embodiment 31, the preparation of 3-dihydroindolin-2-one
[0083]
[0084] 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 36% concentrated hydrochloric acid dropwise to adjust to pH = 3, continue stirring at room temperature for 12h, a solid precipitates, suction filters, washes with water to give a brown solid (0.44g, 61%).
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Abstract
The invention relates to a novel benzisoselenazolone modified pyrroleformate substituted indolone compound and application thereof. The benzisoselenazolone modified pyrroleformate substituted indolone compound provided by the invention is shown as a general formula I, wherein n represents the number of carbon between truss arms and is 2 or 3. The 2-indolone compound of the invention has excellent antitumor activity, and can be widely used in preparing antitumor medicines.
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] Malignant tumor is a common disease that seriously threatens human health. At present, the death caused by malignant tumor accounts for the second place in the death rate of all diseases, second only to cardiovascular and cerebrovascular diseases. And the prevalence of cancer is increasing year by year. Taking my country as an example, the data disclosed in the "2012 China Cancer Registration Annual Report" released by the National Cancer Registry Center shows that on average, one person is diagnosed with cancer every 6 minutes in my country, and the number of new cancer cases every year is about 3.12 million cases. Tumor treatment has become a serious challenge for medical research institutes. [0003] At present, the commonly used antineoplastic drugs in clinical practice are mainly cytotox...
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