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

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,...

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Autores principales: Arumugam, Natarajan, Almansour, Abdulrahman I., Suresh Kumar, Raju, Govindasami, Periyasami, Al-thamili, Dhaifallah M., Krishnamoorthy, Rajapandian, Periasamy, Vaiyapuri Subbarayan, Alshatwi, Ali A., Mahalingam, S. M., Thangamani, Shankar, Menéndez, J. Carlos
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100567/
https://www.ncbi.nlm.nih.gov/pubmed/29734741
http://dx.doi.org/10.3390/molecules23051094
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author Arumugam, Natarajan
Almansour, Abdulrahman I.
Suresh Kumar, Raju
Govindasami, Periyasami
Al-thamili, Dhaifallah M.
Krishnamoorthy, Rajapandian
Periasamy, Vaiyapuri Subbarayan
Alshatwi, Ali A.
Mahalingam, S. M.
Thangamani, Shankar
Menéndez, J. Carlos
author_facet Arumugam, Natarajan
Almansour, Abdulrahman I.
Suresh Kumar, Raju
Govindasami, Periyasami
Al-thamili, Dhaifallah M.
Krishnamoorthy, Rajapandian
Periasamy, Vaiyapuri Subbarayan
Alshatwi, Ali A.
Mahalingam, S. M.
Thangamani, Shankar
Menéndez, J. Carlos
author_sort Arumugam, Natarajan
collection PubMed
description 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 5a–m led to their apoptotic cell death.
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spelling pubmed-61005672018-11-13 Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines Arumugam, Natarajan Almansour, Abdulrahman I. Suresh Kumar, Raju Govindasami, Periyasami Al-thamili, Dhaifallah M. Krishnamoorthy, Rajapandian Periasamy, Vaiyapuri Subbarayan Alshatwi, Ali A. Mahalingam, S. M. Thangamani, Shankar Menéndez, J. Carlos Molecules Article 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 5a–m led to their apoptotic cell death. MDPI 2018-05-05 /pmc/articles/PMC6100567/ /pubmed/29734741 http://dx.doi.org/10.3390/molecules23051094 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Arumugam, Natarajan
Almansour, Abdulrahman I.
Suresh Kumar, Raju
Govindasami, Periyasami
Al-thamili, Dhaifallah M.
Krishnamoorthy, Rajapandian
Periasamy, Vaiyapuri Subbarayan
Alshatwi, Ali A.
Mahalingam, S. M.
Thangamani, Shankar
Menéndez, J. Carlos
Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines
title Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines
title_full Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines
title_fullStr Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines
title_full_unstemmed Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines
title_short Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines
title_sort multicomponent domino synthesis, anticancer activity and molecular modeling simulation of complex dispirooxindolopyrrolidines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100567/
https://www.ncbi.nlm.nih.gov/pubmed/29734741
http://dx.doi.org/10.3390/molecules23051094
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