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Quinoline-benzimidazole salt compound as well as synthesis method and application thereof

Active Publication Date: 2021-11-23
QUJING NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the lead compounds in the prior art (for example: benzimidazolium salt compounds without heterocycles) have poor anti-tumor cell activity

Method used

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  • Quinoline-benzimidazole salt compound as well as synthesis method and application thereof
  • Quinoline-benzimidazole salt compound as well as synthesis method and application thereof
  • Quinoline-benzimidazole salt compound as well as synthesis method and application thereof

Examples

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preparation example Construction

[0055] The present invention also provides a synthetic method of the quinoline-benzimidazolium salt compound described in the above technical scheme, comprising the following steps:

[0056] Mix quinoline, 1-chloromethyl-4-fluoro-1,4-diazobicyclic 2.2.2-octane bis(tetrafluoroborate) (Selectflour), benzimidazole compounds and acetonitrile for Coupling reaction, obtains quinoline-benzimidazole compound;

[0057] The quinoline-benzimidazole compound, the brominated aromatic compound and acetone are mixed for a substitution reaction to obtain the quinoline-benzimidazole salt compound.

[0058] In the present invention, unless otherwise specified, the raw materials used in the present invention are preferably commercially available products.

[0059] In the present invention, quinoline, 1-chloromethyl-4-fluoro-1,4-diazotated bicyclo 2.2.2 octane bis(tetrafluoroborate), benzimidazole compounds and acetonitrile are mixed for coupling Combined reaction to obtain quinoline-benzimidaz...

Embodiment 1

[0085] Quinoline-benzimidazolium salt compound 1 has the following structure:

[0086]

[0087] The preparation process is:

[0088] (1) Quinoline (7.74mmol, 1g) and 1-chloromethyl-4-fluoro-1,4-diazidebicyclo2.2.2octanebis(tetrafluoroborate) (10.06mmol, 3.57 g) Dissolve in 25mL of anhydrous acetonitrile to obtain a quinoline solution, then add benzimidazole (11.61mmol, 1.37g) to the quinoline solution to obtain a coupling reaction system, and stir at 320rpm at room temperature (23°C) Under the conditions of reaction for 6h, after the coupling reaction was completed, the resulting coupling reaction feed liquid was concentrated to 3mL, and the resulting reaction mixture was extracted with dichloromethane (60mL×3) and saturated brine (60mL), and the organic phase, organic phase with anhydrous Na 2 SO 4 After drying, filtering, and distilling off the solvent under reduced pressure, the silica gel column chromatography, the eluent is a mixture of petroleum ether and ethyl ace...

Embodiment 2

[0097] Quinoline-benzimidazolium salt compound 2 has the following structure:

[0098]

[0099] making process:

[0100] (1) The difference from step (1) of Example 1 is only that benzimidazole (11.61mmol, 1.37g) is replaced by 2-methylbenzimidazole (11.61mmol, 1.53g) to obtain quinoline-benzimidazole The mass of the quasi-compound was 1.63 g, and the yield was 81%.

[0101] (2) Dissolve the quinoline-benzimidazole compound (6.29mmol, 1.63g) obtained in step (1) in acetone solvent (30mL), and add 2-bromo-4-methoxyphenethyl Ketone (9.43mmol, 2.16g) was heated (56°C) to reflux for 16h, cooled to room temperature, a solid precipitated out, filtered, washed with ethyl acetate (20mL×3 times), and dried to obtain compound 2 with a mass of 2.67g, the compound 2 is a white powdery solid, and the yield is 87%.

[0102] The high-resolution mass spectrometry detection result of described compound 2 is as follows:

[0103] HRMS calc'd for C 26 h 22 N 3 o 2 + 408.1705,found 408....

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Abstract

The invention belongs to the technical field of medicinal chemistry, and provides a quinoline-benzimidazole salt compound as well as a synthesis method and application thereof. The invention provides a quinoline-benzimidazole salt compound. The quinoline-benzimidazole salt compound has a structure represented by a formula I which is described in the specification. According to the quinoline-benzimidazole salt compound disclosed by the invention, quinoline and an imidazole ring core structure unit are successfully combined together, so that the blank of the quinoline-benzimidazole salt compound is filled, and the provided quinoline-benzimidazole salt compound has good anti-tumor activity.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a quinoline-benzimidazolium salt compound and its synthesis method and application. Background technique [0002] Cancer, also known as malignant tumor, is second only to cardiovascular disease and is the second leading cause of death in the world. About one-sixth of the global population's death is caused by cancer. It is a disease with high morbidity and mortality. Most of the chemotherapeutic drugs in clinical use have side effects such as nausea, vomiting, leukopenia, and bone marrow suppression, which can be life-threatening in severe cases. [0003] Based on the structure of active natural products and compounds with significant biological activity, the strategy of molecular hybridization is used to design and synthesize natural product libraries, from which to screen and find lead compounds with high efficiency, high selectivity, and low toxicity a...

Claims

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Application Information

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IPC IPC(8): C07D401/04A61P35/00
CPCC07D401/04A61P35/00
Inventor 刘正芬羊晓东成飞翔张鸭关
Owner QUJING NORMAL UNIV
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