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Substituted triazole derivatives and their application in the preparation of anti-tumor metastasis drugs
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An anti-tumor metastasis, triazole technology, applied in the field of medicine, can solve the problems of lack of effective treatment methods for tumor metastasis, low effectiveness of small molecules, etc., and achieve the effect of broad anti-tumor metastasis application prospects
Inactive Publication Date: 2020-01-21
ZHEJIANG UNIV
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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.
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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, and then add 3-amino-2-methoxy-N,N- Dimethylbenzamide (Intermediate 1) (97mg, 0.5mmol), continue the reaction for 6h. After the reaction of the raw materials was completed, the solvent was recovered under reduced pressure, the residue was dissolved in water, and extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with saturated brine and 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, CD...
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 = 7.5 Hz, 2H), 1.82–1.72 (m, 2H), 0.97 (t, J = 7.4 Hz, 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 present invention relates to the field of medicine, in particular to triazole derivatives and their application in the preparation of anti-tumor metastasis drugs. Background technique [0002] Due to the increasing incidence and mortality rate year by year, tumors have become a serious public health problem worldwide, and tumor metastasis is one of the key links in the development of tumors. The mechanism of tumor metastasis is complicated. At present, 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 tumor metastasis mechanism and the low effectiveness of small molecule clinical evaluation, there is still a lack of effective treatment methods for tumor metastasis in clinical practice. Therefore, it is very necessary to find highly effective new ...
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