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Substituted triazole derivatives and application thereof in preparing an anti-tumor metastasis drug

A technology of triazoles and derivatives, which is applied in the field of triazole derivatives and their application in the preparation of anti-tumor metastasis drugs, can solve the problems of lack of effective treatment methods for tumor metastasis and low effectiveness of small molecules, etc. Achieve the effect of broad anti-tumor metastasis application prospects

Inactive Publication Date: 2018-06-22
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the complexity of the mechanism of tumor metastasis and the low effectiveness of clinical evaluation of small molecules, there is still a lack of effective treatments for tumor metastasis in clinical practice.

Method used

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  • Substituted triazole derivatives and application thereof in preparing an anti-tumor metastasis drug
  • Substituted triazole derivatives and application thereof in preparing an anti-tumor metastasis drug
  • Substituted triazole derivatives and application thereof in preparing an anti-tumor metastasis drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1.2-Hydroxy-3-((5-phenyl-4H-1,2,4-triazol-3-yl)amino)-N,N-dimethylbenzamide (compound 1)

[0036]

[0037] Step 1. Synthesis of 3-(3-benzoylthioureido)-2-methoxy-N,N-dimethylbenzamide (intermediate 2)

[0038] Dissolve benzoyl chloride (182mg, 1.5mmol) in acetone, slowly add potassium thiocyanate (155mg, 1.6mmol) under stirring, stir at room temperature for 1h, then add 3-amino-2-methoxy-N,N- Dimethylbenzamide (Intermediate 1) (97mg, 0.5mmol), continue to react for 6h. After the reaction of the raw materials was complete, the solvent was recovered under reduced pressure, the residue was dissolved in water, extracted with ethyl acetate (50mL×3), the combined organic layers were washed with saturated brine, anhydrous Na 2 SO 4 After drying, the solvent was recovered under reduced pressure, and the residue was purified by column chromatography to obtain 120 mg of the target product (Intermediate 2) as a white solid, with a yield of 67%; 1 H NMR (500MHz, CDCl ...

Embodiment 2

[0042] Example 2.2-Hydroxy-3-((5-n-propyl-4H-1,2,4-triazol-3-yl)amino)-N,N-dimethylbenzamide (compound 2)

[0043]

[0044] Using Intermediate 1 and n-butyryl chloride as raw materials, according to the method of Example 1, Compound 2 was prepared with a yield of 42%; 1 H NMR (500MHz, Acetone) δ8.20(d, J=8.0Hz, 1H), 7.46(s, 1H), 6.98(d, J=7.8Hz, 1H), 6.85(t, J=7.9Hz, 1H ), 3.15(s, 6H), 2.68(t, J=7.5Hz, 2H), 1.82–1.72(m, 2H), 0.97(t, J=7.4Hz, 3H); ESI-MS: m / z= 290[M+H] + .

Embodiment 3

[0045] Example 3.3-((5-tert-butyl-4H-1,2,4-triazol-3-yl)amino)-2-hydroxy-N,N-dimethylbenzamide (compound 3)

[0046]

[0047] Using intermediate 1 and pivaloyl chloride as raw materials, according to the method of Example 1, compound 3 was prepared with a yield of 36%; 1 H NMR (500MHz, CDCl 3 )δ7.85(d, J=7.4Hz, 1H), 6.84(dd, J=7.8, 1.5Hz, 1H), 6.77(t, J=7.9Hz, 1H), 3.12(s, 6H), 1.36( s,9H); ESI-MS: m / z=304[M+H] + .

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Abstract

The invention discloses substituted triazole derivatives which are a compound shown by the general formula (I) and pharmaceutically acceptable salt thereof; the invention also discloses application ofthe substituted triazole derivatives in preparing an anti-tumor metastasis drug. The novel triazole derivatives and the pharmaceutically acceptable salt thereof prepared in the invention have the advantages of obvious activity of resisting tumor metastasis and broad application prospect in resisting tumor metastasis. The general formula (I) is shown in the description.

Description

technical field [0001] The invention relates to the field of medicines, in particular to triazole derivatives and their application in the preparation of anti-tumor metastasis medicines. Background technique [0002] Due to the increasing incidence and mortality rate year by year, tumor has become a serious public health problem worldwide, and tumor metastasis is one of the key links in the occurrence and development of tumor. The mechanism of tumor metastasis is complex, and some small molecules have been developed for the treatment of tumor metastasis, such as vascular endothelial growth factor receptor (VEGFR) inhibitors, matrix metalloproteinase (MMP) inhibitors, integrin inhibitors and so on. However, due to the complexity of the mechanism of tumor metastasis and the low effectiveness of clinical evaluation of small molecules, there is still a lack of effective treatments for tumor metastasis in clinical practice. Therefore, it is very necessary to find new and efficie...

Claims

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Application Information

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IPC IPC(8): C07D249/14C07D401/12C07D409/12A61K31/4439A61K31/4196A61P35/00A61P35/02
CPCC07D249/14C07D401/12C07D409/12
Inventor 车金鑫董晓武胡永洲盛海潮
Owner ZHEJIANG UNIV