Anthraquinonoimidazole nucleoside analog and synthetic method and application thereof

A technology of anthraquinone-imidazole ribavirin and its synthesis method, which is applied in the fields of chemistry and medicine, can solve the problems affecting and restricting the long-term and extensive use of anthracyclines, and achieve good application prospects and novel structures

Active Publication Date: 2018-11-16
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These have seriously affected and limited the long-term and extensive clinical use of anthracyclines, so many researchers have devoted themselves to the development of low-toxicity anthracyclines

Method used

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  • Anthraquinonoimidazole nucleoside analog and synthetic method and application thereof
  • Anthraquinonoimidazole nucleoside analog and synthetic method and application thereof
  • Anthraquinonoimidazole nucleoside analog and synthetic method and application thereof

Examples

Experimental program
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Embodiment

[0047] 1. Synthesis of glycosyl acceptor 4,11-dihydroxyanthra[2,3-d]imidazole-5,11-dione 5

[0048] Take 8g of compound 1, namely 1,4-dihydroxy-9,10-anthraquinone, in a 250mL round bottom flask, add 100mL of glacial acetic acid, stir and mix evenly, then add 5mL of concentrated nitric acid, heat and stir at 60°C for 3.5h. The reaction solution was filtered, and the filter cake was first washed with 15 mL of glacial acetic acid, and then washed with a large amount of water until neutral, and dried in vacuum to obtain compound 2 with a yield of 69%.

[0049] Take 2.5g of hydroxylamine hydrochloride in a 100mL round-bottom flask, add 80mL of absolute ethanol to dissolve, then add 1.5g of potassium hydroxide, stir for 30min, filter out the KCl white solid, take the filtrate and place it in a 250mL round-bottom flask, and put 2.5g Compound 2 was added to the above filtrate, stirred for 1.5 h, filtered, the filter cake was washed with absolute ethanol and water respectively, and dri...

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Abstract

The invention discloses an anthraquinonoimidazole nucleoside analog and a synthetic method and application thereof, and belongs to the field of chemical and medical technologies. The key points of thetechnical scheme are as follows: the structural formula of an anthraquinonoimidazole nucleoside analog is as shown in the specification. The invention also discloses a synthetic method of the anthraquinonoimidazole nucleoside analog and application of the anthraquinonoimidazole nucleoside analog in the preparation of an anti-cancer drug. By linking various five-membered sugars and six-membered sugars to an anthraquinone compound through imidazoles, a series of anthracene nucleus antibiotics and nucleoside analogs with novel structures and biological activity are obtained.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and specifically relates to a class of anthraquinone imidazole ribavirin analogs and a synthesis method thereof. Background technique [0002] Anthracyclines were first studied as pigment-containing antibiotics isolated from different Streptomyces, and were officially named Anthracycline (ANT) in 1963 because of their significant antiviral and antitumor activities. Anthracycline antibiotics, also known as anthracycline glycoside antibiotics, are composed of a tetracyclic chromophore (aglycone, 7,8,9,10-tetrahydro-5,12-naphthoquinone, formula 1-1 ) are formed by linking one or more sugars or amino sugars through glycosidic bonds. Different anthracyclines have different ligands or sugars. [0003] [0004] Since the isolation of the first anthracycline antibiotic - Daunorubicin (DNR) in 1957 and its application in the clinical treatment of acute leukemia, anthracyclines have beco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/04C07H1/00A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07H1/00C07H19/04
Inventor 毕晶晶张贵生刘青峰程丽丽时蕾
Owner HENAN NORMAL UNIV
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