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Substituted carbazole-imidazolate or benzimidazolium salt compounds, and preparation method thereof

A salt compound, benzimidazole technology, applied in the field of anti-tumor application, can solve the problems that have not been reported in the literature

Inactive Publication Date: 2017-03-29
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A kind of substituted carbazole-imidazolium salt or benzimidazolium salt compound and its preparation method involved in this patent have not been reported in the literature so far

Method used

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  • Substituted carbazole-imidazolate or benzimidazolium salt compounds, and preparation method thereof
  • Substituted carbazole-imidazolate or benzimidazolium salt compounds, and preparation method thereof
  • Substituted carbazole-imidazolate or benzimidazolium salt compounds, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 1-(N-methylcarbazole-3-methyl)-3-(4-methoxyphenacylmethyl)imidazolium bromide

[0022]

[0023] Preparation process: see the above preparation methods A, B, C, D, E for details.

[0024] White solid, 93% yield, m.p. 223-224 o c.

[0025] IR ν max (cm -1 ): 3080, 3016, 2322, 1682, 1600, 1566, 1474, 1443, 1322,1244, 1156, 1120, 1065, 1016, 990, 846, 815, 752, 718, 625.

[0026] 1 H-NMR (400 MHz, DMSO) δ: 9.29 (1H, s), 8.35 (1H, s), 8.14 (1H, d, J =7.7 Hz), 8.02-7.98 (3H, m), 7.76 (1H, s), 7.68 (1H, d, J = 8.4 Hz), 7.62 (2H, d, J = 7.9 Hz), 7.50 (1H, t, J = 7.5 Hz), 7.25 (1H, t, J = 7.5 Hz) , 7.15-7.12 (2H, m), 6.02 (2H, s), 5.70 (2H, s), 3.89 (3H, s), 3.87 (3H, s).

Embodiment 2

[0027] Example 2 1-(N-methylcarbazole-3-methyl)-3-(4-bromophenacylmethyl)imidazolium bromide

[0028]

[0029] Preparation process: see the above preparation methods A, B, C, D, E for details.

[0030] White solid, yield 96%, m.p. 208-209 o c.

[0031] IR ν max (cm -1 ): 3148, 3072, 2325, 1700, 1586, 1565, 1491, 1361, 1335, 1251, 1229, 1120, 1068, 991, 855, 819, 750, 714, 621.

[0032]1 H-NMR (400 MHz, DMSO) δ: 9.20 (1H, s), 8.33 (1H, s), 8.13 (1H, d, J =7.7 Hz), 7.97-7.95 (3H, m), 7.89-7.85 ( 2H, m), 7.72-7.69 (2H, m), 7.65-7.60(2H, m), 7.53-7.49 (1H, m), 7.26 (1H, t, J = 7.5 Hz), 6.02 (2H, s) , 5.69 (2H,s), 3.90 (3H,s).

Embodiment 3

[0033] Example 3 1-(N-methylcarbazole-3-methyl)-3-(2-naphthoylmethyl)imidazolium bromide

[0034]

[0035] Preparation process: see the above preparation methods A, B, C, D, E for details.

[0036] White solid, yield 92%, m.p. 200-201 o c.

[0037] IR ν max (cm -1 ): 3077, 1692, 1627, 1599, 1566, 1494, 1472, 1438, 1362, 1334, 1253, 1159, 1125, 1041, 860, 812, 725, 624.

[0038] 1 H-NMR (400 MHz, DMSO) δ: 9.37 (1H, s), 8.82 (1H, s), 8.38 (1H, s), 8.20-8.10 (3H, m), 8.06-8.03 (3H, m), 7.84-7.82 (1H, m), 7.75-7.62 (5H, m), 7.52-7.49 (1H, m), 7.27-7.24 (1H, m), 6.25 (2H, s), 5.74 (2H, s), 3.90 (3H, s).

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Abstract

The invention discloses a series of substituted carbazole-imidazolate or benzimidazolium salt compounds with a general structure represented by formula I or II, and a preparation method thereof. According to the preparation method, carbazole is taken as a raw material, and the target compound is obtained via five steps including N-methylation, acylation, reduction, combination with imidazole, and salifying. It is shown by results of in vitro antitumor activity cytotoxicity test that the substituted carbazole-imidazolate or benzimidazolium salt compounds possess excellent cytotoxic activity.

Description

technical field [0001] The invention relates to a novel substituted carbazole-imidazolium salt or benzimidazolium salt compound and its preparation method, as well as the anti-tumor application of the pharmaceutical composition in which the compound is an active ingredient. Background technique [0002] Cancer is a class of diseases that seriously threaten human health. The mainstay currently used to treat cancer is chemotherapy. Most of the chemotherapeutic drugs in clinical use have side effects such as nausea, vomiting, leukopenia, and bone marrow suppression. Therefore, finding highly active, non-toxic or low-toxic anticancer compounds has become an important topic in new drug research. [0003] As an important five-membered compound, imidazole widely exists in natural product molecules, and also exists in synthetic drug molecules as an important pharmacophore of physiological activity. As an important nitrogen-containing heterocyclic compound, carbazole and its deriv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06A61K31/4178A61K31/4184A61P35/00
CPCC07D403/06
Inventor 羊晓东张洪彬杨丽娟施义民陈文李良刘建平
Owner YUNNAN UNIV
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