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
Abdulrahman I. Almansour,
Natarajan Arumugam,
Raju Suresh Kumar,
Dhaifallah M. Al-thamili,
Govindasami Periyasami,
Karuppiah Ponmurugan,
Naif Abdullah Al-Dhabi,
Karthikeyan Perumal,
Dhanaraj Premnath
Affiliations
Abdulrahman I. Almansour
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Natarajan Arumugam
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Raju Suresh Kumar
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Dhaifallah M. Al-thamili
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Govindasami Periyasami
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Karuppiah Ponmurugan
Department of Botany and Microbiology, College of Science, King Saud University, Riyadh 11451, Saudi Arabia
Naif Abdullah Al-Dhabi
Department of Botany and Microbiology, College of Science, King Saud University, Riyadh 11451, Saudi Arabia
Karthikeyan Perumal
Department of Chemistry and Biochemistry, The Ohio State University, 151 W. Woodruff Ave, Columbus, OH 43210, USA
Dhanaraj Premnath
Department of Bioscience and Technology, Karunya Institute of Technology and Science, Branch of Bioinformatics, School of Agriculture and Biosciences, Karunya Nagar, Coimbatore-641114, India
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.
