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Benzimidazole-containing Tr*ger's base type compound as well as preparation method and application thereof

A benzimidazole and compound technology, which is applied in the field of drug synthesis, can solve the problems of limited number of chemotherapeutic drugs, cell damage, toxic and side effects, and achieves the effects of low cytotoxicity, mild reaction conditions and simple preparation method

Inactive Publication Date: 2018-11-23
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, the number of chemotherapeutic drugs available clinically is very limited, so discovering new chemotherapeutic drugs that can be used clinically is a very important part of current cancer research
[0003] Most of the existing clinical anticancer drugs have relatively strong toxic and side effects. While killing tumor cells with chemotherapy, they will also cause irreversible damage to normal cells in the human body.

Method used

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  • Benzimidazole-containing Tr*ger's base type compound as well as preparation method and application thereof
  • Benzimidazole-containing Tr*ger's base type compound as well as preparation method and application thereof
  • Benzimidazole-containing Tr*ger's base type compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 0.5mmol 2,8-dialdehyde-TB, 1.2mmol 4-methyl-o-phenylenediamine and 20mL 1,4-dioxane into a 50mL dry eggplant-shaped bottle, and react under reflux at 102°C for 4 hours. After cooling to room temperature, the excess solvent was evaporated under reduced pressure, and the crude product was separated by column chromatography, using methanol: ethyl acetate = 1:8 (V / V) as the eluent, and the product 3a was isolated and purified (yield: 87% ).

[0031] The structural formula of compound 3a is:

[0032]

[0033] The molecular formula is: C 31 h 27 N 6

[0034] Chinese name: 2,8-bis(5-methyl-1H-benzo[d]imidazol-2-yl)-6H,12H-5,11-methyldibenzo[b,f][1, 5] Diazocine

[0035] English name: 2,8-bis(5-methyl-1H-benzo[d]imidazol-2-yl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

[0036] Appearance: black solid

[0037] Melting point: 257.2-259.2°C

[0038] Proton NMR spectrum: 1 H NMR (400MHz, DMSO-d 6 )δ12.60(s,2H),7.93(d,J=7.8Hz,2H),7.79(s,2H),7.41(s,2H),7.32(d,J=...

Embodiment 2

[0042] Add 0.5mmol 2,8-dialdehyde-TB, 1.2mmol 4-methoxy-o-phenylenediamine, and 20mL 1,4-dioxane to a 50mL dry eggplant-shaped bottle, reflux and stir at 102°C for 4 hours, and the reaction is complete After cooling to room temperature, the excess solvent was evaporated under reduced pressure, and the crude product was separated by column chromatography, using methanol:ethyl acetate=1:8 (V / V) as the eluent, and the product 3b was isolated and purified (yield: 81 %).

[0043] The structural formula of compound 3b is:

[0044] The molecular formula is: C 31 h 27 N 6 o 2

[0045] Chinese name: 2,8-bis(5-methoxy-1H-benzo[d]imidazol-2-yl)-6H,12H-5,11-methylenedibenzo[b,f][ 1,5] diazocine

[0046] English name: 2,8-bis(5-methoxy-1H-benzo[d]imidazol-2-yl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

[0047] Appearance: dark gray solid

[0048] Melting point: 234.6-236.4°C

[0049] Proton NMR spectrum: 1 H NMR (400MHz, DMSO-d 6 )δ12.59(s,2H),7.90(s,2H),7.76(s,2H),7.46(s,...

Embodiment 3

[0053] Add 0.5mmol 2,8-dialdehyde-TB, 1.2mmol 4,5-dichloro-o-phenylenediamine and 20mL 1,4-dioxane into a 50mL dry eggplant-shaped bottle, reflux and stir at 102°C for 4h, After the reaction was completed, it was cooled to room temperature, and the excess solvent was evaporated under reduced pressure. The crude product was separated by column chromatography, using methanol:ethyl acetate=1:8 (V / V) as the eluent, and the product 3c was isolated and purified (yield : 89%).

[0054] The structural formula of compound 3c is:

[0055] The molecular formula is: C 29 h 19 Cl 4 N 6

[0056] Chinese name: 2,8-bis(5,6-dichloro-1H-benzo[d]imidazol-2-yl)-6H,12H-5,11-methylenedibenzo[b,f] [1,5]Diazocine

[0057] English name: 2,8-bis(5,6-dichloro-1H-benzo[d]imidazol-2-yl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

[0058] Appearance: light gray solid

[0059] Melting point: >300°C

[0060] Proton NMR spectrum: 1 H NMR (400MHz, DMSO-d 6 )δ13.12(s,2H),7.95(d,J=8.0Hz,2H),7.84...

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Abstract

The invention discloses a benzimidazole-containing Tr*ger's base type compound as well as a preparation method and application thereof. A structural formula of the compound is shown as a formula 3; the compound is prepared by carrying out aldimine condensation reaction on 2,8-dialdehyde-Tr*ger's base and substituted o-phenylenediamine. An in-vivo experiment shows that the benzimidazole-containingTr*ger's base type compound has relatively high inhibition activity on non-small cell lung cancer cells (A549), triple-negative breast cancer cells (231) and triple-positive breast cancer cells (MCF-7), and has low toxicity in human normal cells; the benzimidazole-containing Tr*ger's base type compound can be mixed with human body acceptable acid-forming salt or a medical carrier to form an anti-tumor drug. The invention provides a candidate compound for researching and developing a novel drug for treating triple-negative and triple-positive breast cancer and non-small cell lung cancer. The formula 3 is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis and relates to a base compound, specifically relate to a kind of benzimidazole-containing Base compound and its preparation method and application. Background technique [0002] With the deterioration of the ecological environment and the aging of the world, cancer has already become the second leading cause of death in the world. According to the latest statistics, the number of people who die from cancer every year in the world reaches 8.93 million. Chemotherapy is one of the main measures to treat cancer at present. However, the number of chemotherapeutic drugs available in clinic is very limited, so discovering new chemotherapeutic drugs that can be used clinically is a very important part of current cancer research. [0003] Most of the existing clinical anticancer drugs have relatively strong toxic and side effects. While killing tumor cells with chemotherapy, they will also cau...

Claims

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Application Information

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IPC IPC(8): C07D487/08A61K31/529A61P35/00
CPCA61P35/00C07D487/08
Inventor 吴翚苑睿张鹏王园江宛瑜
Owner XUZHOU NORMAL UNIVERSITY
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