2-(indol-3-yl)-pyridinoimidazole and application thereof

A pyridoimidazole and methyl pyridyl technology, applied in the field of 2--pyridimidazole compounds, can solve the problems of large toxic and side effects, easy generation of drug resistance and the like

Inactive Publication Date: 2019-05-21
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problems that exist are: 1. large toxicity and side effects; 2. easy to produce drug resistance (multidrug resistance / MDR); and vinca alkaloid binding sites, for example, they can be administered orally due to their better water solubility; moreover, they are less prone to multidrug resistance

Method used

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  • 2-(indol-3-yl)-pyridinoimidazole and application thereof
  • 2-(indol-3-yl)-pyridinoimidazole and application thereof
  • 2-(indol-3-yl)-pyridinoimidazole and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1 synthetic compound 1

[0024] Synthesis of Step 1 Compound II

[0025]

[0026] Dissolve 1.0 g of indole-3-carbaldehyde in 15 mL of tetrahydrofuran, then add 0.5 g of sodium hydrogen to the above solution, stir at room temperature for 5 h, then add 1.5 g of benzenesulfonyl chloride, and continue stirring for 8 h. TLC monitoring. After the reaction was completed, water was added to the reaction liquid to quench the reaction, and then extracted with ethyl acetate-water, the ethyl acetate layer was dried with anhydrous sodium sulfate, and the solution was concentrated to obtain 1.7 g of solid compound II. Yield 86.5%.

[0027] The obtained compound II is identified by nuclear magnetic resonance spectrum and mass spectrometry, and the identification results are:

[0028] 1 H NMR (CDCl 3 )δ10.13(s,1H),8.29(m,2H),8.01(m,3H),7.64(t,1H),7.54(t,2H),7.46-7.37(m,2H).MS(ESI )m / z Calcd.For[M+H] + :286.1; found: 286.1.

[0029] Synthesis of Step 2 Compound III...

Embodiment 2

[0043] Synthesis of compound 2

[0044] The synthesis method of compound 2 uses indole-3-carbaldehyde and 4-isoquinoline boronic acid as raw materials, and the method is the same as in Example 1.

[0045]

[0046] Compound 2 was prepared in the same manner as in Example 1 except that the corresponding raw materials were used, and the yield was 40.0%.

[0047] The obtained compound is identified by nuclear magnetic resonance spectrum and mass spectrometry, and the identification results are:

[0048] 1 H NMR (DMSO-d 6 )δ13.13(s,1H),11.80(s,1H),9.49(s,1H),9.03(br,1H),8.69(s,2H),8.31(s,3H),7.77(t,2H ),7.50(d,2H),7.21(br,2H).MS(ESI)m / z Calcd. For[M+H] + :362.1; found: 362.1.

Embodiment 3

[0050] Synthesis of compound 3

[0051] The synthesis method of compound 3 uses indole-3-carbaldehyde and (2-picoline 4-yl)boronic acid as raw materials, and the method is the same as that of Example 1.

[0052]

[0053] Compound 3 was prepared in the same manner as in Example 1 except that the corresponding raw materials were used, and the yield was 41.5%.

[0054] The obtained compound is identified by nuclear magnetic resonance spectrum and mass spectrometry, and the identification results are:

[0055] 1 H NMR (DMSO-d 6 )δ13.16(s,1H),11.88(s,1H),8.85(s,1H),8.75(s,1H),8.63(d,1H),8.58(m,1H),8.35(d,2H ),8.20(d,1H),7.57(s,1H),7.31-7.23(m,2H),2.64(s,3H).MS(ESI)m / z Calcd. For[M+H] + :326.1; found: 326.1.

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Abstract

The invention relates to a 2-(indol-3-yl)-pyridinoimidazole. The chemical structure of the 2-(indol-3-yl)-pyridinoimidazole is represented by formula (I), and R<1> in the formula (I) is a 4-quinolyl group, a 4-isoquinolyl group, a 4-2-methylpyridyl group, a 4-2-methoxypyridyl group or a 4-fluorophenyl group. The 2-(indol-3-yl)-pyridinoimidazole can inhibit tumor cell proliferation, and provides anew inhibitor for inhibiting the tumor cell proliferation.

Description

technical field [0001] The invention relates to organic compounds, in particular to 2-(indol-3-yl)-pyridimidazole compounds, which can inhibit tumor proliferation and can be used for treating tumors. Background technique [0002] Malignant tumor is the most serious type of disease that endangers human health. Its incidence rate is second only to cardiovascular and cerebrovascular diseases, and it is the second largest "killer" of human health. the first place. Therefore, finding and developing new drugs for treating tumors is a major issue at present. [0003] Microtubules play important roles in various cellular processes, including spindle formation, cell shape maintenance and intracellular transport. The function of microtubules in cell mitosis makes them attractive targets for anticancer drugs. Microtubule-targeting agents disrupt microtubule formation to inhibit the entry of cancer cells into G2 / M phase and eventually lead to apoptosis of cancer cells. Therefore, tub...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61P35/00A61K31/444A61K31/4709A61K31/4725A61K31/437
Inventor 陈建军李刚
Owner SOUTHERN MEDICAL UNIVERSITY
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