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9-hydroxymethyl-10-imidazolanthracenehydrazone, and synthetic method and application thereof

A synthetic method, hydroxymethyl technology, applied in the field of medicine, can solve problems such as no synthetic method of 9-hydroxymethyl-10-imanthrene, achieve good potential medicinal value, reduce liver and kidney toxicity, and anti-tumor active effect

Inactive Publication Date: 2013-05-08
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no relevant report about 9-hydroxymethyl-10-imidanthramide and its synthetic method at present

Method used

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  • 9-hydroxymethyl-10-imidazolanthracenehydrazone, and synthetic method and application thereof
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  • 9-hydroxymethyl-10-imidazolanthracenehydrazone, and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Dissolve 0.01mol of 9,10-anthracenedicarbaldehyde and 0.01mol of 4,5-dicyanimidazole-2-hydrazine hydrogen bromide in 50mL of absolute ethanol, and reflux at 78°C until complete (TLC Tracking detection, about 3h), stop the reaction, cool the reaction solution to room temperature, let it stand for 1h, precipitate an orange solid, filter, and dry the obtained solid in vacuum at room temperature for 10h to obtain a mixed product with a yield of 55%;

[0034] 2) The product A was subjected to silica gel column chromatography, eluted with a mixed solvent composed of anhydrous methanol and dichloromethane with a volume ratio of 1:50, tracked and detected by thin layer chromatography, and the eluate containing the target component was collected. The obtained eluate is concentrated and dried to obtain the target intermediate;

[0035] 3) Take 0.01mol of the target intermediate, heat it with 30mL of anhydrous methanol and dissolve it into a clear solution; take 0.05mol of NaBH...

Embodiment 2

[0045] 1) Dissolve 0.01mol of 9,10-anthracenedicarbaldehyde and 0.01mol of 4,5-dicyanimidazole-2-hydrazine hydrogen bromide in 100mL of anhydrous methanol, and reflux at 70°C until complete (TLC Tracking detection, about 3h), stop the reaction, cool the reaction solution to 20°C, let it stand for 2h, precipitate an orange solid, filter, and dry the obtained solid in vacuum to obtain product A with a yield of 65%;

[0046] 2) The product A was subjected to silica gel column chromatography, eluted with a mixed solvent composed of anhydrous methanol and chloroform with a volume ratio of 1:70, tracked and detected by thin layer chromatography, and the eluate containing the target component was collected, and the obtained eluted Deliquoring, concentrating and drying to obtain the target intermediate;

[0047] 3) Take 0.01mol of the target intermediate, heat it with 20mL of anhydrous methanol and dissolve it into a clear solution; take 0.02mol of NaBH 4 , dissolved into a clear sol...

Embodiment 3

[0049] 1) Dissolve 0.01mol of 9,10-anthracenedicarbaldehyde and 0.01mol of 4,5-dicyanimidazole-2-hydrazine hydrogen bromide in 80mL of absolute ethanol, and reflux at 120°C until complete (TLC Tracking detection, about 3h), stop the reaction, cool the reaction solution to 25°C, let it stand for 4h, precipitate an orange solid, filter, and dry the obtained solid in vacuum to obtain product A with a yield of 60%;

[0050] 2) The product A was subjected to silica gel column chromatography, eluted with a mixed solvent composed of anhydrous methanol and ethyl acetate with a volume ratio of 1:100, tracked and detected by thin layer chromatography, and the eluate containing the target component was collected. The obtained eluate is concentrated and dried to obtain the target intermediate;

[0051] 3) Take 0.01mol of the target intermediate, heat it with 30mL of anhydrous methanol and dissolve it into a clear solution; take 0.015mol of NaBH 4 , dissolved in 5mL of anhydrous methanol ...

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Abstract

The invention discloses a new antharcycline anticancer medicine derivative 9-hydroxymethyl-10-imidazolanthracenehydrazone, and a synthetic method and an application thereof. The synthetic method of 9-hydroxymethyl-10-imidazolanthracenehydrazone comprises the following steps: weighing 9,10-anthracenedicarboxaldehyde and 4,5-dihydroimidazol-2-ylhydrazine hydrobromide having a same molar amount with 9,10-anthracenedicarboxaldehyde, mixing them, dissolving them in an organic solvent, and carrying out an aldehyde-amine condensation reaction to obtain mixed products; carrying out silica gel column chromatography of the mixed products, eluting with a mixed solvent comprising methanol and one of dichloromethane, chloroform and ethyl acetate, concentrating the obtained eluate, and drying to obtain a target intermediate; and carrying out a reducing reaction of the target intermediate and sodium borohydride in the presence of an alcoholic solvent, adding water to the reaction solution, allowing the obtained solution to stand and precipitate, and separating to obtain a solid which is 9-hydroxymethyl-10-imidazolanthracenehydrazone. A case that 9-hydroxymethyl-10-imidazolanthracenehydrazone has substantial in-vitro resistance activities on a plurality of human tumor cells, has substantial propagation inhibition activities on some tested tumor strains, has a good potential medicinal value, and is excepted to be used for the preparation of various antitumor medicines is found in the invention.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to 9-hydroxymethyl-10-imidanthracene and its synthesis method and application. Background technique [0002] Anthracycline anticancer drugs are an important class of anticancer antibiotics. Such as doxorubicin, idarubicin, aclacinomycin, mitoxantrone and bisantrene, etc., can inhibit the synthesis of DNA or RNA, most of which belong to Cycle nonspecific anticancer drugs. These compounds have been widely used in clinical chemotherapy, and also play an important role in combined chemotherapy regimens such as CEF, AC and CAF. [0003] The anticancer activity of anthracyclines is based on their anthracycline mother nucleus: anthracycline has a good planar structure, so it can effectively intercalate into the base pairs of DNA and irreversibly bind to the double helix of DNA, and eventually lead to DNA chain breaks cause tumor cell death; in addition, the side chains on anthracycline...

Claims

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Application Information

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IPC IPC(8): C07D233/52A61K31/4168A61P35/00
Inventor 刘延成陈振锋梁宏王海璐
Owner GUANGXI NORMAL UNIV
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