Naphthoquinone-fused triazole core skeleton derivative compound, preparation method and application thereof

A naphthoquinonetriazole and compound technology, applied in the field of organic chemistry, can solve the problems of uncontrollable proliferation, metastasis and drug resistance of tumor cells and tumor stem cells, and achieve the effect of inhibiting the action of nuclear transcription factor STAT3

Active Publication Date: 2019-09-10
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In normal cells, STAT3 is transiently activated and tightly regulated to regulate cell growth, differentiation, survival and apoptosis, but in cancer cells, STAT3 is an oncogene, highly expressed and continuously activated, promoting downstream target Overexpression or downregulation of genes and proteins, leading to uncontrolled proliferation, metastasis and drug resistance of tumor cells and cancer stem cells

Method used

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  • Naphthoquinone-fused triazole core skeleton derivative compound, preparation method and application thereof
  • Naphthoquinone-fused triazole core skeleton derivative compound, preparation method and application thereof
  • Naphthoquinone-fused triazole core skeleton derivative compound, preparation method and application thereof

Examples

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Embodiment 1

[0044] This example shows 34 kinds of naphthoquinonotriazole core skeleton derivative compounds with different structures and their preparation methods according to the present invention, wherein the 34 naphthoquinonetriazole core skeleton derivative compounds with different structures are represented by compound codes.

[0045] (1) The compound code is HY034503, a naphthoquinonotriazole core skeleton derivative compound, and its structural formula is as follows:

[0046]

[0047] The preparation method of the above compound HY034503: Weigh 141mg (0.76mmol) 4-methylbenzyl bromide and dissolve it in DMF, stir for 5min, add dropwise 100mg (1.54mmol) sodium azide solution (DMF solution), argon protection, 25 Reflux at ℃, stir for 4 hours, TLC detects that the reaction is complete, add 10ml of pure water, extract with EtOAc, wash the organic phase with water, MgSO 4 Drying, suction filtration, concentration and drying, then it was dissolved with EtOAc, added to the reaction fla...

Embodiment 2

[0321] This example further demonstrates that the naphthoquinone triazole core skeleton derivative compound of the present invention has the function of inhibiting nuclear transcription factor STAT3, inhibiting tumor (stem) cell growth and inducing tumor (stem) cell apoptosis through pharmacological and pharmacodynamic experiments. effect of death.

[0322] (1) Effects of naphthoquinonetriazole core skeleton derivatives on IL-6-induced STAT3 gene expression in tumor cells.

[0323] Experimental method: In this experiment, the Luciferase reporter gene method was used to detect the effect of naphthoquinone triazole core skeleton derivatives on the STAT3 signal transduction pathway. The agonist IL-6 can induce the activation of the STAT3 signaling pathway in human liver cancer cells HepG2, through The inhibition rate of STAT3 signaling pathway activation was detected to display the results.

[0324] After the HepG2 / STAT3 cells grow to the logarithmic growth phase, collect the ce...

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Abstract

The invention relates to a naphthoquinone-fused triazole core skeleton derivative compound, relates to a preparation method and application of the naphthoquinone-triazole core skeleton derivative compound, and belongs to the field of organic chemistry. The provided naphthoquinone-triazole core skeleton derivative compound has a structural formula represented by the following formula (I) in the specification, wherein X is a C or N atom; R1, R2, R3, R4, R5, R6, R7 and R8 are separately independently any one of hydrogen, halogens, hydroxyl, cyano, sulfydryl, amino, nitro, nitroso, alkyl, alkoxy,ester group, carboxyl and sulfonyl. The application of the provided naphthoquinone-triazole core skeleton derivative compound or a pharmaceutically acceptable salt or hydrate thereof in preparation ofdrugs for treating diseases in which STAT3 signal transduction is abnormal is provided.

Description

technical field [0001] The invention relates to a naphthoquinonetriazole core skeleton derivative compound, and also relates to a preparation method and application of the naphthoquinonetriazole core skeleton derivative compound, belonging to the field of organic chemistry. Background technique [0002] STAT3 (signal transducer and activator of transcription3) is the signal transduction and activator of transcription 3. The STAT3 protein consists of about 770 amino acids and has a molecular weight of about 92,000. According to its function and structure, it can be divided into SH2 domain, DNA binding domain, Supercoiled domain, linker domain and amino terminal domain. As a cytoplasmic protein, STAT3 is activated and phosphorylated by cytokines such as IL-6, JAKs and EGFR, and transferred into the nucleus in the form of p-STAT3, acting on specific DNA fragments in the nucleus to regulate the transcription of target genes. In normal cells, STAT3 is transiently activated and t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/18C07D471/04A61P35/00
CPCC07D249/18C07D471/04A61P35/00
Inventor 刘嘉炜俞强马洪艳张卿曾馨玲文靓曦刘景丽
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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