Imidazole Antimicrobial via Ionic Liquid Synthesis

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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, as conventional antibiotics face increasing resistance, and existing methods for synthesizing organic compounds often involve hazardous solvents and inefficient processes.

Innovation Solution

The synthesis of 4,5-bis(4-bromophenyl)-1-hexyl-2-(3-pyridyl)-1H-imidazole via a one-pot four-component reaction using 4,4′-dibromobenzil, hexylamine, 3-pyridinecarboxaldehyde, and ammonium acetate in pyridinium hydrogen sulfate, which demonstrates excellent antimicrobial activity against various microbes, including gram-positive and gram-negative bacteria, and fungi.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If conventional synthesis methods are used, then chemical transformations can be achieved, but hazardous solvents and volatile organic compounds are generated, increasing environmental harm

Engineering Contradiction:
Improvehazardous solvents and volatile organic compoundsVSAvoidsynthesis efficiency
Core Design Contradiction:
Object-affected harmful factorsVSProductivity

Solution Approach 1:

The patent changes the reaction parameters by employing ionic liquids as solvents instead of conventional volatile organic solvents. This parameter change maintains synthesis efficiency while eliminating hazardous VOC emissions, aligning with green chemistry principles

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent converts the previously harmful volatile organic solvents into beneficial ionic liquid solvents that are non-volatile and environmentally friendly. The ionic liquids provide similar dissolution capabilities without the harmful VOC emissions, turning a harmful factor into a beneficial one

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

2Reliability

If conventional antibiotics are used, then bacterial infections can be treated, but bacterial resistance increases, reducing treatment effectiveness

Engineering Contradiction:
Improveantimicrobial effectivenessVSAvoidbacterial resistance
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent develops new antimicrobial compounds with novel chemical structures that can effectively target resistant bacteria. These new compounds represent fresh therapeutic options that can overcome existing resistance mechanisms, similar to how disposable items provide fresh solutions without carrying forward previous failures

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent creates composite antimicrobial agents with specific molecular structures combining multiple functional groups (imidazole, pyridine, bromophenyl moieties) to achieve enhanced antimicrobial activity against resistant strains through synergistic interactions of different chemical groups

Inventive Principle:
Principle #40Composite materials

3Productivity

If traditional synthesis methods are used, then chemical reactions can proceed, but reaction times are longer and conditions are more severe, reducing process efficiency

Engineering Contradiction:
Improvereaction speed and efficiencyVSAvoidreaction conditions severity
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent uses ionic liquids as intermediary substances that facilitate the chemical reaction under milder conditions. The ionic liquids act as mediators that lower the energy barrier for reaction, enabling faster reaction rates at lower temperatures compared to traditional methods

Inventive Principle:
Principle #24Intermediary (Mediator)

Data Source

PatentUS11958828B14,5-bis(4-bromophenyl)-1-hexyl-2-(3-pyridyl)-1H-imidazole as an antimicrobial compound
Publication Date: 2024.04.16 KING FAISAL UNIV
  • US11958828B1 patent drawing
  • US11958828B1 patent drawing
  • US11958828B1 patent drawing

AI summary

An 4,5-bis(4-bromophenyl)-1-hexyl-2-(3-pyridyl)-1H-imidazole compound, its synthesis, and its use as an antimicrobial agent.