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

An expedient synthesis of hitherto unexplored novel hybrid heterocycles comprising dispiropyrrolidine, <i>N</i>-styrylpiperidone and indeno[1,2-<i>b</i>]quinoxaline units has been developed via domino multicomponent 1,3-dipolar cycloaddition strategy employing a new class of...

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Bibliographic Details
Main Authors: Abdulrahman I. Almansour, Natarajan Arumugam, Raju Suresh Kumar, Dhaifallah M. Al-thamili, Govindasami Periyasami, Karuppiah Ponmurugan, Naif Abdullah Al-Dhabi, Karthikeyan Perumal, Dhanaraj Premnath
Format: Article
Language:English
Published: MDPI AG 2019-05-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/24/10/1962
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Summary:An expedient synthesis of hitherto unexplored novel hybrid heterocycles comprising dispiropyrrolidine, <i>N</i>-styrylpiperidone and indeno[1,2-<i>b</i>]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 <i>N</i>-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 <b>8f</b>, <b>8h</b>, and <b>8l</b> displayed significant activity against tested microbial pathogens. The synergistic effect revealed that the combination of compound <b>8h</b> with streptomycin and vancomycin exhibited potent synergistic activity against <i>E. coli</i> ATCC 25922. In addition, molecular docking simulation has also been studied for the most active compound.
ISSN:1420-3049