Anthraquinonotriazole antibiotic nucleoside analog, synthetic method and application in preparation of antineoplastic or antiviral drug

A technology for anthraquinone triazole and nucleoside analogs, which is used in the fields of chemistry and medicine to achieve good anti-tumor and anti-viral activities, and to overcome the effects of toxic and side effects such as cardiotoxicity and drug resistance.

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

AI Technical Summary

Problems solved by technology

If anthracyclines can be combined with sugar groups in the form of triazoles to form new anthraquinone triazole anthracycline antibiotics and nucleoside analogs, it is likely to obtain new anti-tumor or anti-viral drugs. However, there are currently no reports on this

Method used

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  • Anthraquinonotriazole antibiotic nucleoside analog, synthetic method and application in preparation of antineoplastic or antiviral drug
  • Anthraquinonotriazole antibiotic nucleoside analog, synthetic method and application in preparation of antineoplastic or antiviral drug
  • Anthraquinonotriazole antibiotic nucleoside analog, synthetic method and application in preparation of antineoplastic or antiviral drug

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Embodiment

[0043]

[0044] 1. Synthesis of glycosyl ligand 4,11-dihydroxyanthra[2,3-d][1,2,3]triazole-5,10-dione

[0045] Step S1: Add 6 g of compound 1 to 90.0 mL of glacial acetic acid, then add 5.0 mL of concentrated nitric acid, heat and stir at 60°C for 3.5 h, filter the reaction solution, wash the filter cake with AcOH and water, and then dry to obtain compound 2 , the yield is 62%;

[0046] Step S2: Dissolve 500 mg of hydroxylamine hydrochloride in 15.0 mL of absolute ethanol, add 300 mg of potassium hydroxide, stir for 30 min, filter out KCl white solid to obtain the filtrate, add 500 mg of compound 2 to the above filtrate, stir for 1.5 h, filter, filter The cake was washed with absolute ethanol and water respectively, and then dried in an oven at 30°C to obtain compound 3 with a yield of 96%;

[0047] Step S3: Add 20.6g of sodium sulfide to 120.0mL of a mixed solvent of ethanol and water with a volume ratio of 3:1, then add 2.6g of compound 3 to the above solution, then add ...

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Abstract

The invention discloses an anthraquinonotriazole antibiotic nucleoside analog, a synthetic method and application of the anthraquinonotriazole antibiotic nucleoside analog in the preparation of an antineoplastic or antiviral drug, and belongs to the field of chemical and medical technologies. According to the key points of the technical scheme, the structural formula of the anthraquinonotriazole antibiotic nucleoside analog is as shown in the specification. The invention also specifically discloses a synthetic method of the anthraquinonotriazole antibiotic nucleoside analog and application ofthe anthraquinonotriazole antibiotic nucleoside analog in the preparation of an antineoplastic or / and antiviral drug. A series of anthraquinonotriazole antibiotic nucleoside analogs with novel structure and bioactivity are prepared in the invention. It is found through biological activity tests that the compounds have good antineoplastic and antiviral activity and can be used for preparation of anantineoplastic or antiviral drug so as to furthermore effectively overcome toxic and side effect such as cardiotoxicity, drug resistance and the like generated by the current long-term use of anthracene nucleus antibiotic drugs.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and specifically relates to a class of anthraquinone triazole antibiotic nucleoside analogs, a synthesis method and an application in preparing antitumor or antiviral drugs. Background technique [0002] The parent anthracycline of anthracycline antibiotics has a planar structure, which is the main part embedded in DNA, and can form adducts with DNA to firmly combine with DNA. For this reason, many scientists currently introduce anthracyclines into nucleosides, and act with normal nucleosides to form oligonucleotides, which further form double-helix or triple-helix DNA fragments. The introduction of this anthracycline greatly enhanced the thermal stability of the double-helix and triple-helix DNA fragment structures. This class of adducts of anthracyclines and nucleosides has attracted attention due to this new form of conjugation, which will play an important role in the study of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/04C07H1/00A61P35/00A61P35/02A61P31/12
CPCA61P31/12A61P35/00A61P35/02C07H1/00C07H19/04
Inventor 毕晶晶张贵生张冰刘青峰夏丁丁
Owner HENAN NORMAL UNIV
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