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Synthesis and bioactivity evaluation of 1-indoleacetic acid-5-nitroimidazole-containing derivative thereof

A technology of indoleacetic acid and nitroimidazole, which can be used in drug combination, organic chemistry, antitumor drugs, etc., can solve problems such as easy isomerization

Inactive Publication Date: 2015-03-25
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the cis double bonds in CA-4 and its cis analogues are prone to isomerization during storage and handling, so a large number of modifications in CA-4 are concentrated on the connecting bridge

Method used

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  • Synthesis and bioactivity evaluation of 1-indoleacetic acid-5-nitroimidazole-containing derivative thereof
  • Synthesis and bioactivity evaluation of 1-indoleacetic acid-5-nitroimidazole-containing derivative thereof
  • Synthesis and bioactivity evaluation of 1-indoleacetic acid-5-nitroimidazole-containing derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Example 1: Preparation of (E)-2-(2-(2-chlorostyryl)-5-nitroimidazole)ethanolindole-3-carboxylic acid (3a)

[0014]

[0015] Add compound 2 (5mmol) into a 25mL round bottom flask containing 15mL DMF, stir until dissolved, then add isoquinoline-3-carboxylic acid (5mmol), dissolve and add K 2 CO 3 (5 mmol) as catalyst. The reaction was carried out under reflux overnight (TLC followed the reaction until there was little or no at least one raw material), and the crude product was obtained, and the product was purified by column chromatography with ethyl acetate / hexane ratio of 1:9 to obtain the target compound. product. Yield 64.5%.m.p.189~191℃; 1 H NMR (DMSO-d 6 , 300MHz) δ: 11.71(s, 1H), 8.23(s, 1H), 7.95-7.69(m, 4H), 7.58(t, J=7.9Hz, 2H), 7.33(t, J=7.5Hz, 2H ), 7.14-7.02(m, 3H), 5.02(t, J=4.3Hz, 2H), 4.65(t, J=4.4Hz, 2H).

Embodiment 2

[0016] Example 2: Preparation of (E)-2-(2-(3-chlorostyryl)-5-nitroimidazole)ethanolindole-3-carboxylic acid (3b)

[0017]

[0018] The preparation method is the same as in Example 2. (E)-2-(2-(3-chlorostyryl)-5-nitroimidazole)ethanol-4-methylbenzenesulfonic acid is used instead of (E)-2-(2- (2-chlorostyryl)-5-nitroimidazole)ethanol-4-methylbenzenesulfonic acid to obtain the title compound. Yield yield 66.5%.m.p.188~190℃; 1 H NMR (DMSO-d 6 , 300MHz) δ: 11.68(s, 1H), 8.26(t, J=7.9Hz 2H), 8.06(d, J=8.4Hz, 2H), 7.76(t, J=8.4Hz, 4H), 7.29(t , J=8.5Hz, 1H), 7.19-7.00(m, 3H), 5.03(t, J=4.3Hz, 2H), 4.65(t, J=4.4Hz, 2H)

Embodiment 3

[0019] Example 3: Preparation of (E)-2-(2-(4-chlorostyryl)-5-nitroimidazole)ethanolindole-3-carboxylic acid (3c)

[0020]

[0021] The preparation method is the same as in Example 2. (E)-2-(2-(4-chlorostyryl)-5-nitroimidazole)ethanol-4-methylbenzenesulfonic acid is used instead of (E)-2-(2- (2-chlorostyryl)-5-nitroimidazole)ethanol-4-methylbenzenesulfonic acid to obtain the title compound. Yield 67.5%.m.p.188~189℃; 1 H NMR (DMSO-d 6 , 300MHz) δ: 11.77(s, 1H), 8.22(s, 1H), 7.89(t, J=10.1Hz, 2H), 7.77(d, J=2.7Hz, 1H), 7.69-7.59(m, 3H ), 7.44-7.31(m, 3H), 7.14-7.02(m, 2H), 4.99(t, J=4.4Hz, 2H), 4.62(t, J=4.3Hz, 2H).

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Abstract

The invention provides synthesis of 1-indoleacetic acid-5-nitroimidazole-containing derivative. The derivative is characterized by having a general formula as shown in the specification, wherein R is 3a:o-Cl; 3b:m-Cl; 3c:p-Cl; 3d:o-Br; 3e:m-Br; 3f:p-Br; 3g:o-NO2; 3h:m-NO2; 3i:p-NO2; 3j:o-CH3; 3k:m-CH3; 3l:p-CH3; 3m:o-OCH3; 3n:m-OCH3; 3o:p-OCH3; 3p:2,4-2Cl; 3q:fused Ph; 3r:H. The 1-indoleacetic acid-5-nitroimidazole-containing derivative has a remarkable inhibiting effect on a human lung adenocarcinoma cell line (A549), a human cervical carcinoma cell line (HELA) and a human astrocytoma cell line (U251), and can be applied to preparation of anti-tumor medicines. The invention further discloses a preparation method of the derivative.

Description

technical field [0001] The invention relates to the synthesis, preparation and application of a class of 1-indoleacetic acid-5-nitroimidazole derivatives as anti-malignant cell proliferation agents and anticancer drugs. Background technique [0002] Microtubules are the main components of the cytoskeleton, composed of α-tubulin and β-tubulin heterodimers, and have the characteristics of a hollow tubular structure. In addition, there is a kind of γ-tubulin, which is not a component of microtubules, but participates in the assembly of microtubules. Microtubules have the dynamic characteristics of polymerization and depolymerization, and play an important role in the process of maintaining cell shape, cell division, signal transduction and material transport. Microtubules aggregate into spindles in the early stage of cell division, and the spindles pull chromosomes to move to the two poles in mitosis and enter the two daughter cells to complete cell proliferation. Because mic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12A61P35/00
CPCC07D403/12
Inventor 朱海亮汤丹洁段勇涛陶翔翔
Owner NANJING UNIV
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