Application of dibenzimidazolamine compound to preparation of antimicrobial medicine

A benzimidazolamide and compound technology, applied in the field of medicinal chemistry, can solve the problems of low antibacterial and antifungal activity, and achieve the effects of solving drug resistance, strong in vitro antimicrobial activity, and simple structure

Inactive Publication Date: 2016-02-03
LINYI UNIVERSITY
View PDF2 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the defects of low antibacterial and antifungal activitie...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Application of dibenzimidazolamine compound to preparation of antimicrobial medicine
  • Application of dibenzimidazolamine compound to preparation of antimicrobial medicine
  • Application of dibenzimidazolamine compound to preparation of antimicrobial medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The bisbenzimidazolamine compound in this example has a structure shown in formula II, and its preparation method comprises the following steps:

[0027]

[0028] Add 5.701g of N-((1H-benzimidazol-2-yl)methyl)-4-methylaniline VI-1, 3.312g of potassium carbonate and 60mL of acetonitrile into a 100mL round bottom flask, and stir at 50°C After 0.5 hours, add 2.621g of 1,4-bis(bromomethyl)benzene VII-1 again, heat up to 70°C for reaction, track the reaction by thin-layer chromatography until the end of the reaction, cool to room temperature, and remove acetonitrile by distillation under reduced pressure. The mixture of petroleum ether and ethyl acetate with a volume ratio of 5:1 was used as an eluent for silica gel column chromatography purification and drying to obtain 3.118 g of bis-benzimidazolamide compound II-1 as a white solid. The rate is 54%; the melting point is 167-168°C; 1 HNMR (300MHz, CDCl 3 )δppm: 2.23 (s, 6H, 4, 4'-CH 3 Ph), 4.59(s, 4H, benzimidazole-CH...

Embodiment 2

[0031] The bisbenzimidazolamine compound described in this embodiment has a structure shown in formula III, and its preparation method comprises the following steps:

[0032]

[0033] Add 4.068g of secondary amine compound VI-2, 1.935g of sodium bicarbonate and 50mL of ethanol to a 100mL round-bottomed flask, and stir at 60°C for 0.5 hours, then add 3.312g of dibromocompound VII-2, and continue stirring Carry out the reaction, follow the thin layer chromatography to the end of the reaction, cool to room temperature, and distill off the ethanol under reduced pressure, and the residue is purified by silica gel column chromatography with a mixture of petroleum ether and ethyl acetate in a volume ratio of 6:1 as the eluent. , and dried to obtain 2.591g of syrupy bis-benzimidazolamine compound III, with a yield of 47%; 1 HNMR (300MHz, CDCl 3 )δppm: 0.88-0.93(t, 6H, J=7.5Hz, ((CH 2 ) 3 CH 3 ) 2 ), 1.22-1.48 (m, 8H, (CH 2 C 2 h 4 CH 3 ) 2 ), 2.41-2.47 (t, 4H, J=9.0Hz, (CH ...

Embodiment 3

[0035] The bisbenzimidazolamine compound described in this embodiment has a structure shown in formula V, and its preparation method comprises the following steps:

[0036]

[0037] Add 6.335g of secondary amine compound VI-3, 2.010g of sodium hydroxide and 60mL of methanol to a 100mL round-bottomed flask, control the temperature at 50°C and stir for 0.5 hours, then add 2.351g of dibromocompound VII-3, control the temperature for 60 ℃ to continue the reaction, thin-layer chromatography tracking to the end of the reaction, cooled to room temperature, vacuum distillation to remove methanol, the residue with a volume ratio of 5:1 petroleum ether and ethyl acetate mixture as eluent for silica gel column layer Analysis, purification, and drying yielded 3.213 g of bis-benzimidazolamine compound V as a white solid, with a yield of 49% and a melting point of 167-168° C.; 1 HNMR (300MHz, CDCl 3 )δppm: 3.67-3.69 (m, 4H, CH 2 CH 2 ), 3.72 (s, 6H, 3, 3'-OCH 3 Ph), 4.58(s, 4H, benzi...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides an application of a dibenzimidazolamine compound to preparation of an antimicrobial medicine. The dibenzimidazolamine compound has a structure shown as formula (I), and is simple in structure. The dibenzimidazolamine compound is relatively good in in-vitro antimicrobial activity, and performs quite high inhibitory activity of gram positive bacteria, such as staphylococcus aureus, methicillin-resistant staphylococcus aureus, bacillus subtilis, and micrococcus luteus, gram negative bacteria, such as escherichia coli, proteus vulgaris, pseudomonas aeruginosa, and salmonella typhi, and fungi, such as candida utilis, aspergillus flavus, saccharomyces cerevisiae, candida albicans, and candida. The dibenzimidazolamine compound is used for preparing an antibacterial and/or antifungal medicine.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to the use of a novel drug small molecule compound bis-benzimidazolamide in the preparation of antimicrobial drugs. Background technique [0002] As a condensed ring of imidazole and benzene ring, benzimidazole has a large conjugated structure and strong intramolecular electron transfer ability. Coordination and hydrophobic interaction, π-π stacking, electrostatic interaction, etc. Therefore, benzimidazole compounds can undergo a variety of non-covalent bond interactions, exhibit some special properties, and show broad application prospects and great development value in many fields such as medicine, pesticides, chemistry, and physics. [0003] In recent years, drug molecules constructed with benzimidazole rings have shown a wide range of biological activities, such as antibacterial, antifungal, antiviral, anticancer, anti-inflammatory and analgesic, as hist...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): A61K31/4184A61P31/04A61P31/10
CPCY02A50/30
Inventor 张慧珍王慧刘凤志
Owner LINYI UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap