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New 3'-azido daunorubicin-13-thiosemicarbazone compound with cancer resistance and preparation method thereof

A compound, phenyl technology, applied in the field of chemistry and medicine, achieves the effect of simple synthesis method and good biological activity

Inactive Publication Date: 2012-07-25
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Anthracycline antibiotics all contain a four-membered fused ring system and a deoxysugar structure, have strong anticancer activity, and are among the most effective anticancer drugs, but they produce irreversible cardiotoxicity during treatment, such as myocardial Diseases and drug resistance also limit their clinical application

Method used

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  • New 3'-azido daunorubicin-13-thiosemicarbazone compound with cancer resistance and preparation method thereof
  • New 3'-azido daunorubicin-13-thiosemicarbazone compound with cancer resistance and preparation method thereof
  • New 3'-azido daunorubicin-13-thiosemicarbazone compound with cancer resistance and preparation method thereof

Examples

Experimental program
Comparison scheme
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Embodiment Construction

[0017] 1. Synthesis of substituted thiosemicarbazides I-3 to I-18

[0018]

[0019] Add 50mmol of substituted ammonia, 50mmol of carbon disulfide and 50mmol of triethylamine into the reaction flask, cool to 0°C and react overnight. Wash the reaction solution with ether and dry it for 30 minutes, dissolve the obtained solid in 45 mL of anhydrous chloroform and neutralize 50 mmol of triethylamine, add 50 mmol of ethyl chloroformate dropwise at 0°C, and react for 2 hours. Compounds I-3 to I-18 can be obtained through analysis and purification with yields of 50-80%.

[0020]

[0021] 2.1 Synthesis of 3-substituted hydrazone-3'-azidodaunorubicin (II series compounds)

[0022]

[0023] At room temperature, ADNR (1mmol) and series I compounds (3eq) were added to a 50mL round bottom flask, 10mL absolute ethanol and 1 drop of acetic acid were added, and the reaction process was monitored by TLC. After the reaction, use column chromatography to separate and obtain II series c...

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Abstract

The invention discloses a new 3'--azido daunorubicin-13-thiosemicarbazone compound with cancer resistance and a preparation method thereof. The preparation method comprises the following specific steps: reacting 3'-azido daunorubicin with various thiosemicarbazide to synthesize the new 3'-azido-daunorubicin-13-thiosemicarbazone compound. The compound shows high activity in the activity test of cancer cells.

Description

technical field [0001] The invention relates to a new 3'-azidodaunorubicin-13-semisemicarbazide (thio)urea compound with anticancer activity and a preparation method, belonging to the technical field of chemistry and medicine. Background technique [0002] In the 1960s, anthracycline antibiotics such as daunorubicin and doxorubicin have been used as first-line antitumor drugs in clinical treatment and have been greatly developed. Anthracycline antibiotics contain a four-membered fused ring system and a deoxysugar structure, have strong anticancer activity, and are among the most effective anticancer drugs, but they produce irreversible cardiotoxicity during treatment, such as myocardial Diseases and drug resistance also limit their clinical application. [0003] [0004] In order to overcome the above shortcomings, in 2006, Lanyan Fang, Guisheng Zhang et al. (J.Med.Chem.2006,49,932-941) reported the 3'-NH of daunorubicin 2 converted to N 3 The new compound 3′-azidodaun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/252A61K31/704A61P35/00A61P35/02
Inventor 张贵生刘青锋张志国时蕾
Owner HENAN NORMAL UNIV
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