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Substituted benzoxanthone type compound and application thereof

A kind of technology of benzoxanthone and compound, applied in benzoxanthone compound and its application field in pharmacy, can solve the problem such as in vivo activity reduction, toxicity, achieve the effect of good antitumor activity

Inactive Publication Date: 2011-05-25
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Camptothecin is a classic topoisomerase I inhibitor. At present, two drugs, topotecan and irinotecan, have entered clinical use. However, the E lactone ring of camptothecin compounds is easily hydrolyzed in vivo to form a Active carboxylate salt form, which significantly reduces its in vivo activity and leads to its obvious toxicity

Method used

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  • Substituted benzoxanthone type compound and application thereof
  • Substituted benzoxanthone type compound and application thereof
  • Substituted benzoxanthone type compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1: Synthesis of 8,10-hydroxybenzoxanthone

[0068] Put 10g of 1-hydroxy-2-naphthoic acid, 10g of phloroglucinol and 30g of zinc chloride in 70mL of phosphorus oxychloride, react at 70°C for 6 hours, stop the reaction, add 1.5L of water after cooling, stir overnight, pump A dark red solid was obtained by filtration and purified by column chromatography (THF:PE 1:8) to obtain 5.3 g of light yellow solid 8,10-hydroxybenzoxanthone (35.8%). 1 H NMR (500MHz, CDCl 3 ), δ12.91(s, 1H), 10.24(s, 1H), 8.62(d, J=7.9Hz, 1H), 8.14(d, J=8.7Hz, 1H), 7.94(d, J=7.9Hz , 1H), 7.72 (m, 3H), 6.60 (d, J=1.9Hz, 1H), 6.36 (d, J=1.9Hz, 1H).

Embodiment 2

[0069] Example 2: Synthesis of 8-hydroxy-10-methoxy-7H-benzoxanthone

[0070] According to the method of Example 1, 3,5-dimethoxyphenol was used instead of phloroglucinol to obtain 5.6 g of light yellow solid 8-hydroxyl-10-methoxyl-7H-benzoxanthone (36.1%) .

[0071] 1 H NMR (500MHz CDCl 3 ), δ12.94(s, 1H), 8.64(d, J=7.9Hz, 1H), 8.19(d, J=8.7Hz, 1H), 7.95(d, J=7.9Hz, 1H), 7.72(m , 3H), 6.65(d, J=1.9Hz, 1H), 6.43(d, J=1.9Hz, 1H), 3.94(s, 1H).

Embodiment 3

[0072] Example 3: Synthesis of 9,11-dibromo-8,10-dihydroxy-7H-benzoxanthone

[0073] Add 0.50g of 8,10-hydroxybenzoxanthone to 10mL of acetic acid, add 0.18mL of bromine dropwise, react at room temperature for 2h, and filter with suction to obtain 0.71g of yellow solid 9,11-dibromo-8,10-dihydroxy -7H-Benzoxanthone (91.0%). 1 H NMR (500MHz, CDCl 3 ) δ 7.70 (m, 3H), 7.91 (m, 1H), 8.16 (d, J=8.7Hz, 1H), 8.74 (m, 1H), 13.97 (s, 1H).

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Abstract

The invention relates to the technical field of medicine, in particular to a new benzoxanthone type compound and an application thereof in pharmacy. Benzoxanthone type derivatives are one type of topoisomerase I inhibitors in new structure, which are found in recent years, and have obvious cell proliferation activity. The invention provides the new benzoxanthone type compound and pharmaceutical salts thereof, and the structure of the compound is as shown in the general formula (I). The invention further provides the application of the benzoxanthone type compound and the pharmaceutical salts thereof in the preparation of the topoisomerase inhibitors, anti-tumor medicaments, antifungal medicaments, antiviral medicaments, anti-hypertensive medicaments or anti-thrombotic medicaments.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a new class of benzoxanthone compounds and their application in pharmacy. Background technique [0002] Camptothecin is a classic topoisomerase I inhibitor. At present, two drugs, topotecan and irinotecan, have entered clinical use. However, the E lactone ring of camptothecin compounds is easily hydrolyzed in vivo to form a The active carboxylate form significantly reduces its in vivo activity and leads to its obvious toxicity. In order to solve the problem of camptothecin, non-camptothecin topoisomerase I inhibitors such as benzophenanthridine compounds, indenoisoquinolinones and indolocarbazoles have been obtained in recent years. [0003] Benzoxanthone derivatives are topoisomerase I inhibitors with a new structure discovered in recent years, and have obvious inhibitory activity on cell proliferation (such as Hee-Ju Cho et al.: New benzoxanthone derivatives as topoisomerase ...

Claims

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Application Information

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IPC IPC(8): C07D311/78C07D335/04C07D405/06A61K31/352A61K31/382A61K31/4433A61P35/00A61P31/10A61P31/12A61P9/12A61P7/02A61P43/00
Inventor 张万年缪震元程鹏飞盛春泉姚建忠祝令建张永强郭巍刘文锋庄春林
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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