Benzo(c)acridine derivative, and preparation method and use thereof

A derivative, acridine technology, used in the field of anti-tumor drugs and medicine, can solve the problems of enhanced anti-cancer activity and weak anti-cancer activity, and achieve the effects of increased purity, strong anti-tumor activity, and increased yield

Active Publication Date: 2016-04-13
嘉兴笼列电子商务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Acridine is a class of nitrogen-containing organic heterocyclic compounds that has received widespread attention. Because its structure is a macrocyclic conjugated system with a rigid planar structure, it can be used as an intercalator for macromolecules such as DNA. It has anti-tumor, anti-virus, and anti-malarial , antibacterial, bioluminescent probes and treatment of AIDS, etc. have shown strong physiological activity, the inventor disclosed a kind of acridine amidothiourea derivatives and its The preparation method and application, using acridine as the parent, the synthesis of acridine amidothiourea derivatives has anticancer activity, but the anticancer acti

Method used

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  • Benzo(c)acridine derivative, and preparation method and use thereof
  • Benzo(c)acridine derivative, and preparation method and use thereof
  • Benzo(c)acridine derivative, and preparation method and use thereof

Examples

Experimental program
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Example Embodiment

[0025] Example 1

[0026] A benzo(c)acridine derivative, which has the structural formula:

[0027]

[0028] The synthetic route of the benzo(c)acridine derivative is as follows:

[0029]

[0030] The preparation of 7-benzo (c) acridine benzamide thiourea ④, the specific steps are as follows:

[0031] The following raw materials are calculated in parts by weight:

[0032] 1) In a three-necked flask, add 12 parts of o-bromobenzoic acid, 8 parts of naphthylamine, 13 parts of potassium carbonate and 0.9 parts of copper powder, add 65 parts of n-pentanol as a solvent, react at 100°C for 1 hour, and remove under reduced pressure After n-pentanol, add 400 parts of water and react at 60℃ for 20 minutes. After filtering, wash the filter cake with water, collect the washed water and combine the filtrate, acidify with concentrated hydrochloric acid to pH 2, and precipitate a large amount of purple black precipitate , Suction filtration, the obtained black solid is recrystallized with acetone, a...

Example Embodiment

[0039] Example 2

[0040] A benzo(c)acridine derivative, which has the structural formula:

[0041]

[0042] The synthetic route of the benzo(c)acridine derivative is as follows:

[0043]

[0044] The preparation of 7-benzo (c) acridine benzamide thiourea ④, the specific steps are as follows:

[0045] The following raw materials are calculated in parts by weight:

[0046] 1) In a three-necked flask, add 20 parts of o-bromobenzoic acid, 12 parts of naphthylamine, 10 parts of potassium carbonate and 1.0 part of copper powder, add 150 parts of n-pentanol as a solvent, react at 105°C for 1.5 hours, and remove under reduced pressure After n-amyl alcohol, add 1000 parts of water and react at 100℃ for 10 minutes. After filtering, wash the filter cake with water, collect the washed water and combine the filtrate, acidify with concentrated hydrochloric acid to pH 1.5, and precipitate a large amount of purple black precipitate , Suction filtration, the obtained black solid is recrystallized wit...

Example Embodiment

[0051] Example 3

[0052] A benzo(c)acridine derivative, which has the structural formula:

[0053]

[0054] The synthetic route of the benzo(c)acridine derivative is as follows:

[0055]

[0056] The preparation of 7-benzo (c) acridine benzamide thiourea ④, the specific steps are as follows:

[0057] The following raw materials are calculated in parts by weight:

[0058] 1) In a three-neck flask, add 40 parts of o-bromobenzoic acid, 25 parts of naphthylamine, 31 parts of potassium carbonate and 2.5 parts of copper powder, add 100 parts of n-pentanol as a solvent, react at 180°C for 1 hour, and remove under reduced pressure After n-pentanol, add 1100 parts of water and react at 50℃ for 15 minutes. After filtration, wash the filter cake with water, collect the washed water and combine the filtrate, acidify with concentrated hydrochloric acid to pH 2.5, and precipitate a large amount of purple black precipitate , Suction filtration, the obtained black solid is recrystallized with aceton...

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Abstract

The invention discloses a benzo(c)acridine derivative, and a preparation method and a use thereof. The chemical title of the benzo(c)acridine derivative is 7-benzo(c)acridinylamidothiourea, and the derivative has a structural formula shown in the description. The invention also discloses an application of the derivative in the preparation of antitumor drugs. The derivative can be combined with pharmaceutically acceptable auxiliary materials to prepare an injection, a tablet, a pill, a capsule, a suspension or an emulsion. Benzoacridine has stronger activity than acridine as a mother ring, and the novel benzo(c)acridine derivative is synthesized through connecting the 7-position of the benzo(c)acridine ring with an active group amidothiourea structure, so activity is superposed, and the anticancer activity of the benzo(c)acridine derivative is greatly higher than that of acridinylamidothiourea derivatives.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to the technical field of antineoplastic drugs, in particular to a benzo(c)acridine derivative and a preparation method and use thereof. Background technique [0002] Tumor is still one of the most common and serious diseases that directly threaten human life in the world today. According to incomplete statistics, about 7 million people in the world are newly diagnosed with cancer every year, and more than 5 million people die of cancer every year. With the research of biochemistry, immunology, therapeutics and other fields, as well as the understanding of tumor gene level and the new progress in the field of biology and technology, pharmacists and oncologists are increasingly aware that, It is necessary to start with the mechanism of tumor occurrence and development in order to improve the curative effect and achieve breakthrough progress. DNA is an ideal biological target in th...

Claims

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Application Information

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IPC IPC(8): C07D219/10A61K31/473A61P35/00
CPCC07D219/10
Inventor 霍丽妮陈睿李培源苏炜钟伟鹏覃方玲
Owner 嘉兴笼列电子商务有限公司
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