Domino Multicomponent Approach for the Synthesis of Functionalized Spiro-Indeno[1,2- b ]quinoxaline Heterocyclic Hybrids and Their Antimicrobial Activity, Synergistic Effect and Molecular Docking Simulation

An expedient synthesis of hitherto unexplored novel hybrid heterocycles comprising dispiropyrrolidine, -styrylpiperidone and indeno[1,2- ]quinoxaline units has been developed via domino multicomponent 1,3-dipolar cycloaddition strategy employing a new class of azomethine ylide in ionic liquid, 1-but...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2019-05, Vol.24 (10), p.1962
Main Authors: Almansour, Abdulrahman I, Arumugam, Natarajan, Suresh Kumar, Raju, Al-Thamili, Dhaifallah M, Periyasami, Govindasami, Ponmurugan, Karuppiah, Al-Dhabi, Naif Abdullah, Perumal, Karthikeyan, Premnath, Dhanaraj
Format: Article
Language:English
Subjects:
Antiinfectives and antibacterials
Antimicrobial activity
Antimicrobial agents
Bacteria
Binding sites
Cancer
Cycloaddition
dispiropyrrolidine
docking studies
domino multicomponent reaction
Drug resistance
Gram-positive bacteria
Hybrids
Hydrogen
indeno[1,2-b]quinoxaline
Investigations
Ionic liquids
Microorganisms
Molecular docking
Pathogens
Quinoxaline
Quinoxalines
Salmonella
Simulation
Streptomycin
Synergistic effect
Vancomycin
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Summary:An expedient synthesis of hitherto unexplored novel hybrid heterocycles comprising dispiropyrrolidine, -styrylpiperidone and indeno[1,2- ]quinoxaline units has been developed via domino multicomponent 1,3-dipolar cycloaddition strategy employing a new class of azomethine ylide in ionic liquid, 1-butyl-3-methylimidazolium bromide. This domino protocol involves, 1,3-dipolar cycloaddition and concomitant enamine reaction affording the dispiropyrrolidine tethered -styrylpiperidone hybrid heterocycles in moderate to good yield in a single step. These compounds were evaluated for their antimicrobial activity against bacterial and fungal pathogens, therein compounds , , and displayed significant activity against tested microbial pathogens. The synergistic effect revealed that the combination of compound with streptomycin and vancomycin exhibited potent synergistic activity against ATCC 25922. In addition, molecular docking simulation has also been studied for the most active compound.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24101962