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Novel antitumor compound and preparation method and application thereof

A technology of anti-tumor drugs and compounds, which is applied in the field of medicine and anti-tumor drugs, and can solve the problems of anti-tumor drugs that cannot meet the needs of treatment, are easily mutated, and chemotherapy fails.

Inactive Publication Date: 2011-08-03
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the tumor has the ability to metastasize in the early stage, about 50% of the patients with clinically diagnosed primary tumors have developed distant metastases. More than 100% is related to the multidrug resistance of tumor cells, and the antitumor drugs currently used in clinical practice are far from meeting the requirements of treatment

Method used

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  • Novel antitumor compound and preparation method and application thereof
  • Novel antitumor compound and preparation method and application thereof
  • Novel antitumor compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] The preparation of the compound of embodiment 1 structural formula 1

[0106] 1) 2-methyl-8-methoxy-6,7-methylenedioxy-1-(6-nitrophthalide-3-yl)-1,2,3,4-tetrahydroisoquine Preparation of morphine

[0107] Dissolve 2 g of cotanine (refer to Journal of Organic Chemistry 1990, 55: 3767-3771 for the synthesis method) in 9 ml of absolute ethanol, stir to dissolve, add 1.62 g of 6-nitrophthalide, and reflux for 3 hours under nitrogen protection , a large amount of precipitation occurred. Cool, filter with suction, wash with a small amount of absolute ethanol, and dry to obtain 3.05 g of a yellow solid with a yield of 90.8%.

[0108] 2) 2-methyl-8-methoxy-6,7-methylenedioxy-1-(6-aminophthalide-3-yl)-1,2,3,4-tetrahydroisoquinoline preparation of

[0109] 0.27 g of 2-methyl-8-methoxy-6,7-methylenedioxy-1-(6-nitrophthalide-3-yl)-1,2,3,4-tetrahydro Put isoquinoline in a 10ml eggplant-shaped bottle, add 1.08ml glacial acetic acid to dissolve, then quickly add 1.08ml concentrat...

Embodiment 2

[0112] The preparation of the compound of embodiment 2 structural formula 2

[0113] 2-methyl-8-methoxy-6,7-methylenedioxy-1-(6-aminophthalide-3-yl)-1,2,3,4-tetra Hydroisoquinoline reacts with p-fluorobenzoyl chloride, and the reaction conditions are the same as in Example 1, thereby obtaining 2-methyl-8-methoxy-6,7-methylenedioxy-1-(6-p-fluorobenzene Formamidophthalide-3-yl)-1,2,3,4-tetrahydroisoquinoline. Yield 50%. 1 H-NMR (DMSO-d 6 ): 1.82-2.59 (m, 4H, CH 2 CH 2 ), 2.45(s, 3H, NCH 3 ), 3.99 (s, 3H, OCH 3 ), 4.31(d, 1H, CH-N), 5.69(d, 1H, CH-O), 6.02(s, 2H, OCH 2 O), 6.49-8.26 (m, 8H, Ar-H), 10.83 (s, 1H, CONH). MS (EI) m / z (M + )490.

Embodiment 3

[0114] The preparation of the compound of embodiment 3 structural formula 3

[0115] 2-methyl-8-methoxy-6,7-methylenedioxy-1-(6-aminophthalide-3-yl)-1,2,3,4-tetra Hydroisoquinoline reacts with o-chlorobenzoyl chloride, and the reaction conditions are the same as in Example 1, thereby obtaining 2-methyl-8-methoxy-6,7-methylenedioxy-1-(6-o-chlorobenzene Formamidophthalide-3-yl)-1,2,3,4-tetrahydroisoquinoline. Yield 11.2%.

[0116] 1 H-NMR (DMSO-d 6 ): 1.83-2.56 (m, 4H, CH 2 CH 2 ), 2.45(s, 3H, NCH 3 ), 3.99 (s, 3H, OCH 3 ), 4.31(d, 1H, CH-N), 5.69(d, 1H, CH-O), 6.02(s, 2H, OCH 2 O), 6.49-8.26 (m, 8H, Ar-H), 10.83 (s, 1H, CONH) MS (EI) m / z (M + )506.

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Abstract

The invention provides a novel antitumor compound 2-methyl-8-methoxyl group-6, 7-methylene dioxy group-1-(6-substitution aminobenzene phthaleins-3-radical)-1, 2, 3, 4-tetrahydroisoquinoline as shown in the constitutional formula below, wherein, R is unsubstituted or substituted aryl formoxyl, aryl sulfonyl, alkyl formoxyl or alkyl; the invention further provides a preparation method and application of the novel antitumor compound; the novel antitumor compound of the invention is 2-methyl-8-methoxyl group-6, 7-methylene dioxy group-1-(6-substitution aminobenzene phthaleins-3-radical)-1, 2, 3, 4-tetrahydroisoquinoline, 6-bit aminogroup of phthalide group thereof is substituted by various alkyl or acyl, thus enjoying fine antitumor activity and laying sound foundation for developing the novelantitumor compound and bring good news to the tumor patients.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular to the technical field of antitumor drugs, and specifically refers to a novel antitumor compound and its preparation method and application. Background technique [0002] Malignant tumor has become a common disease that seriously endangers people's life and health. According to incomplete statistics, there are about 20 million new cases in the world every year; in my country, there are about 1.6-2 million new cases and 1.3 million deaths each year. Because the tumor has the ability to metastasize in the early stage, about 50% of the patients with clinically diagnosed primary tumors have developed distant metastases. More than % is related to the multidrug resistance of tumor cells, and the antitumor drugs currently used in clinical practice are far from meeting the requirements of treatment. [0003] 2-Methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxyphthalide-3-yl)-1,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61P35/00C07D491/056A61K31/4741
Inventor 郑剑斌闻韧戴厚玲周福生刘建文郭磊
Owner EAST CHINA UNIV OF SCI & TECH
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