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Article

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

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Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
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Department of Botany and Microbiology, College of Science, King Saud University, Riyadh 11451, Saudi Arabia
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Department of Chemistry and Biochemistry, The Ohio State University, 151 W. Woodruff Ave, Columbus, OH 43210, USA
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Department of Bioscience and Technology, Karunya Institute of Technology and Science, Branch of Bioinformatics, School of Agriculture and Biosciences, Karunya Nagar, Coimbatore-641114, India
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Author to whom correspondence should be addressed.
Academic Editor: Pawel Kafarski
Molecules 2019, 24(10), 1962; https://doi.org/10.3390/molecules24101962
Received: 18 April 2019 / Revised: 19 May 2019 / Accepted: 20 May 2019 / Published: 22 May 2019
(This article belongs to the Special Issue Design and Synthesis of Bioactive Compounds)
An expedient synthesis of hitherto unexplored novel hybrid heterocycles comprising dispiropyrrolidine, N-styrylpiperidone and indeno[1,2-b]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 N-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 8f, 8h, and 8l displayed significant activity against tested microbial pathogens. The synergistic effect revealed that the combination of compound 8h with streptomycin and vancomycin exhibited potent synergistic activity against E. coli ATCC 25922. In addition, molecular docking simulation has also been studied for the most active compound. View Full-Text
Keywords: domino multicomponent reaction; dispiropyrrolidine; indeno[1,2-b]quinoxaline; docking studies; antimicrobial activity; synergistic effect domino multicomponent reaction; dispiropyrrolidine; indeno[1,2-b]quinoxaline; docking studies; antimicrobial activity; synergistic effect
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MDPI and ACS Style

Almansour, A.I.; Arumugam, N.; Suresh Kumar, R.; Al-thamili, D.M.; Periyasami, G.; Ponmurugan, K.; Al-Dhabi, N.A.; Perumal, K.; Premnath, D. 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. Molecules 2019, 24, 1962. https://doi.org/10.3390/molecules24101962

AMA Style

Almansour AI, Arumugam N, Suresh Kumar R, Al-thamili DM, Periyasami G, Ponmurugan K, Al-Dhabi NA, Perumal K, Premnath D. 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. Molecules. 2019; 24(10):1962. https://doi.org/10.3390/molecules24101962

Chicago/Turabian Style

Almansour, Abdulrahman I., Natarajan Arumugam, Raju Suresh Kumar, Dhaifallah M. Al-thamili, Govindasami Periyasami, Karuppiah Ponmurugan, Naif A. Al-Dhabi, Karthikeyan Perumal, and Dhanaraj Premnath. 2019. "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" Molecules 24, no. 10: 1962. https://doi.org/10.3390/molecules24101962

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