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Molecules 2018, 23(5), 1094; https://doi.org/10.3390/molecules23051094

Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines

1
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
2
Nanobiotecnology and Molecular Biology Research Laboratory, Department of Food Science and Nutrition, College of Food and Agricultural Sciences, King Saud University, Riyadh 11451, Saudi Arabia
3
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, USA
4
Department of Pathology and Population Medicine, College of Veterinary Medicine, Midwestern University, Glendale, AZ 85308, USA
5
Unidad de Química Orgánica y Farmacéutica, Departamento de Química en Ciencias Farmacéuticas, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain
*
Authors to whom correspondence should be addressed.
Received: 17 April 2018 / Revised: 29 April 2018 / Accepted: 3 May 2018 / Published: 5 May 2018
(This article belongs to the Special Issue Design in Synthetic Biology)
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Abstract

A series of spirooxindolopyrrolidine fused N-styrylpiperidone heterocyclic hybrids has been synthesized in excellent yield via a domino multicomponent protocol that involves one-pot three component 1,3-dipolar cycloaddition and concomitant enamine reactions performed in an inexpensive ionic liquid, namely 1-butyl-3-methylimidazolium bromide ([bmim]Br). Compounds thus synthesized were evaluated for their cytotoxicity against U-937 tumor cells. Interestingly; compounds 5i and 5m exhibited a better cytotoxicity than the anticancer drug bleomycin. In addition; the effect of the synthesized compounds on the nuclear morphology of U937 FaDu cells revealed that treatment with compounds 5am led to their apoptotic cell death. View Full-Text
Keywords: domino reaction; 1,3-dipolar cycloaddition; ionic liquids; cytotoxicity assays; molecular docking domino reaction; 1,3-dipolar cycloaddition; ionic liquids; cytotoxicity assays; molecular docking
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Arumugam, N.; Almansour, A.I.; Suresh Kumar, R.; Govindasami, P.; Al-thamili, D.M.; Krishnamoorthy, R.; Periasamy, V.S.; Alshatwi, A.A.; Mahalingam, S.M.; Thangamani, S.; Menéndez, J.C. Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines. Molecules 2018, 23, 1094.

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