Naphthalimide benzimidazole compound, preparation method and application thereof

A technology of naphthalimide and benzimidazole, which is applied in the field of medicinal chemistry, can solve the problems of undiscovered antimicrobial activity and excellent compounds, and achieves the effects of strong in vitro antimicrobial activity, simple structure and resistance to drug resistance.

Active Publication Date: 2020-03-06
LINYI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, some studies have introduced the benzimidazole ring into the naphthalimide structure in order to obtain drug lead molecules with significant antimicrobial activity, but unfortunately, no compounds with excellent antimicrobial activity have been found.

Method used

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  • Naphthalimide benzimidazole compound, preparation method and application thereof
  • Naphthalimide benzimidazole compound, preparation method and application thereof
  • Naphthalimide benzimidazole compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of naphthalimide benzimidazole compound I-1, the reaction formula is as follows:

[0030]

[0031] Specific steps are as follows:

[0032] Weigh 1.195g of 4-bromo-1,8-naphthalimide, 10.912g of 2-(chloromethyl)-1-propyl-1H-benzimidazole III-10.912g and 0.768g of potassium carbonate in a 100mL round bottom flask , add a small amount of DMF to dissolve the system, put the round bottom flask into an oil bath, install a reflux device, heat and stir the reaction at 60°C, track with thin layer chromatography until the end of the reaction, cool to room temperature, and remove the organic solvent DMF by distillation under reduced pressure The residue was obtained, and the residue was separated and purified by silica gel column chromatography, using a mixture of dichloromethane and acetone with a volume ratio of 20:1 as the eluent, and the separated product was dried to obtain the brown syrupy naphthoyl Imine benzimidazole compound I-1.

[0033] The present embod...

Embodiment 2

[0036] Naphthalimide benzimidazole compound I-2, the reaction formula is as follows:

[0037]

[0038] Specific steps are as follows:

[0039] Weigh 1.204g of 4-bromo-1,8-naphthalimide, 2-(chloromethyl)-1-hexyl-1H-benzimidazole III-21.097g and 0.837g of potassium carbonate in a 100mL round bottom flask, Add a small amount of DMF to dissolve the system, put the round-bottomed flask into an oil bath, install a reflux device, heat and stir the reaction at 60°C, follow up with thin-layer chromatography until the end of the reaction, cool to room temperature, and distill off the organic solvent DMF under reduced pressure to obtain The residue is separated and purified by silica gel column chromatography, using a mixture of dichloromethane and acetone at a volume ratio of 20:1 as the eluent, and the separated product is dried to obtain the brown syrupy naphthalene Ambenzimidazole compound I-2.

[0040] The present embodiment yield 51%; 1 H NMR (400MHz, DMSO-d 6 ):δ0.73(t,3H,J...

Embodiment 3

[0046] Adopt the 96-hole microdilution method of the clinical experiment standard (National Committee for Clinical Laboratory Standards, NCCLS) that meets the American National Committee formulate in 1993, the naphthalimide benzimidazole compound that embodiment 1-2, comparative example 1 make In vitro antimicrobial activity test, testing these compounds against Staphylococcus aureus, MASR, Micrococcus luteus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Proteus, Candida utilis, Aspergillus flavus, Saccharomyces cerevisiae The minimum inhibitory concentration (MIC) for Candida albicans and Candida.

[0047] The specific test method is: dissolve the compound to be tested with a small amount of dimethyl sulfoxide, then dilute it with water to make a solution with a concentration of 1.28 mg / mL, then dilute it to 1024 μg / mL with culture medium, and incubate at 35°C for 24-72 hours. After the culture plate was placed on a shaker and fully stirred, the MIC value was ...

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Abstract

Belonging to the technical field of pharmaceutical chemistry, the invention discloses a naphthalimide benzimidazole compound, a preparation method and application thereof. The compound has strong in-vitro antimicrobial activity, especially shows very high inhibitory activity to staphylococcus aureus, methicillin-resistant staphylococcus aureus, bacillus subtilis, micrococcus luteus and other gram-positive bacteria, escherichia coli, proteus, pseudomonas aeruginosa, salmonella typhi and other gram-negative bacteria, candida utilis, aspergillus flavus, saccharomyces cerevisiae, candida albicans,candida mycoderma bacteria and other fungi, can be used for preparation of antibacterial and/or antifungal drugs, and is conducive to solving increasingly serious drug resistance, stubborn pathogenicmicroorganisms, newly emerging harmful microorganisms and other clinical treatment problems.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a naphthalimide benzimidazole compound and a preparation method and application thereof. Background technique [0002] Cyclic imines have attracted much attention due to their broad potential applications in the field of antimicrobial, especially antibacterial. Naphthalimides are a class of cyclic imines with strong hydrophobicity and large conjugated systems, which can interact with various active targets in life systems through non-covalent bonding forces such as π-π stacking. It exhibits a wide range of biological activities, such as anticancer, antibacterial, antitrypanosomal and analgesic, etc. So far, many naphthalimide compounds have been used in the field of anti-tumor, and some derivatives such as naphfemate and elinefade have entered clinical trials, mainly by embedding deoxyribonucleic acid (DNA) to exert anti-tumor effect. Due to its remarka...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06A61P31/04A61P31/10
CPCC07D401/06A61P31/04A61P31/10Y02A50/30
Inventor 张慧珍赵志龙刘芸竹侯杰梁文靖钟文文
Owner LINYI UNIVERSITY
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