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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,...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2018
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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. |
format | Online Article Text |
id | pubmed-6100567 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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