Imidazole Derivative Synthesis via Ionic Liquid and Ultrasound

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Solution Overview

Problem

There is a growing need for new antimicrobial agents effective against drug-resistant microorganisms, particularly bacteria and fungi, due to increasing antibiotic resistance, and existing methods for synthesizing organic compounds often involve hazardous solvents and inefficient processes.

Innovation Solution

The synthesis of 4-(4,5-bis(4-bromophenyl)-2-(4-methoxyphenyl)-1H-imidazol-1-yl)butanoic acid using a one-pot three-component reaction in Pyridinium Ionic Liquid as a catalyst and solvent, combined with ultrasonic techniques, to produce an eco-friendly compound with demonstrated antimicrobial activity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional antibiotics are used to treat bacterial infections, then treatment effectiveness is reduced, but antimicrobial resistance increases

Engineering Contradiction:
Improvetreatment effectivenessVSAvoidantimicrobial resistance
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of imidazole derivatives through multi-component reactions, creating new compounds with altered pharmacological properties that can overcome existing antimicrobial resistance while maintaining treatment effectiveness

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining multiple components (aldehydes, amino acids, beta-dicarbonyl compounds) into complex imidazole derivative molecules, resulting in compounds with enhanced and multifaceted antimicrobial activity against resistant strains

Inventive Principle:
Principle #40Composite materials

2Productivity

If traditional synthesis methods are used for organic compounds, then production is achieved, but hazardous substances and environmental pollution increase

Engineering Contradiction:
Improvesynthesis efficiencyVSAvoidhazardous substances
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the physical and chemical parameters of the synthesis process by using ionic liquids as solvents and ultrasound irradiation as energy source, achieving high yields and purity while eliminating hazardous volatile organic solvents and reducing energy consumption

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention replaces traditional thermal heating mechanisms with ultrasound irradiation (mechanical vibration at high frequency), enabling chemical transformations under milder conditions with shorter reaction times and reduced energy input, thereby reducing harmful emissions

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

3Productivity

If multi-component reactions are used for synthesis, then productivity and environmental friendliness improve, but reaction complexity increases

Engineering Contradiction:
Improvesynthesis efficiencyVSAvoidreaction complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent uses ionic liquids as intermediary substances that facilitate multi-component reactions by providing a unique reaction environment with adjustable properties, enabling multiple components to react simultaneously in one pot while simplifying product isolation and purification

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention demonstrates universality by showing that the same ionic liquid catalyst and ultrasound methodology can be applied to various multi-component reactions different imidazole derivatives, streamlining the synthesis process across different molecular targets

Inventive Principle:
Principle #6Universality (Multi-functionality)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The compound exhibits excellent antimicrobial activity against various bacterial and fungal strains, including Bacillus cereus, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Aspergillus flavus, and Chrysosporium keratinophilum, offering a promising therapeutic option while employing a greener, more efficient synthesis method.

Implementation Method 1

Pyridinium Ionic Liquid as a catalyst and green solvent

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

an ultrasonic technique is used as a source of heat

Methodology Applied
Scientific EffectUltrasonic heating: Ultrasonic Vibration

Data Source

PatentUS11945783B14-(4,5-bis(4-bromophenyl)-2-(4-methoxyphenyl)-1H-imidazol-1-yl)butanoic acid as an antimicrobial compound
Publication Date: 2024.04.02 KING FAISAL UNIV
  • US11945783B1 patent drawing
  • US11945783B1 patent drawing
  • US11945783B1 patent drawing

AI summary

An 5-(4,5-bis(4-bromophenyl)-2-(4-methoxyphenyl)-1H-imidazol-1-yl)pentanoic compound, its synthesis, and its use as an antimicrobial agent.