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Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol

BACKGROUND: Spiropyrrolidine tethered piperidone heterocyclic hybrids were synthesized with complete regio- and stereoselectively in excellent yield via a tandem three-component 1,3-dipolar cycloaddition and subsequent enamine reaction in [bmim]Br. The synthesized compounds were evaluated for their...

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Autores principales: Arumugam, Natarajan, Almansour, Abdulrahman I., Kumar, Raju Suresh, Al-thamili, Dhaifallah M., Periyasami, Govindasami, Periasamy, V. S., Athinarayanan, Jegan, Alshatwi, Ali A., Mahalingam, S. M., Menéndez, J. Carlos
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6119554/
https://www.ncbi.nlm.nih.gov/pubmed/30173362
http://dx.doi.org/10.1186/s13065-018-0462-x
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author Arumugam, Natarajan
Almansour, Abdulrahman I.
Kumar, Raju Suresh
Al-thamili, Dhaifallah M.
Periyasami, Govindasami
Periasamy, V. S.
Athinarayanan, Jegan
Alshatwi, Ali A.
Mahalingam, S. M.
Menéndez, J. Carlos
author_facet Arumugam, Natarajan
Almansour, Abdulrahman I.
Kumar, Raju Suresh
Al-thamili, Dhaifallah M.
Periyasami, Govindasami
Periasamy, V. S.
Athinarayanan, Jegan
Alshatwi, Ali A.
Mahalingam, S. M.
Menéndez, J. Carlos
author_sort Arumugam, Natarajan
collection PubMed
description BACKGROUND: Spiropyrrolidine tethered piperidone heterocyclic hybrids were synthesized with complete regio- and stereoselectively in excellent yield via a tandem three-component 1,3-dipolar cycloaddition and subsequent enamine reaction in [bmim]Br. The synthesized compounds were evaluated for their anticancer activity against FaDu hypopharyngeal tumor cells. FINDINGS: Interestingly, most compounds displayed cytotoxicities similar to the standard anticancer agent bleomycin, with two of them (5a and 5g) being slightly more active than the reference drug. CONCLUSION: Synthesized compounds have also been evaluated for their apoptosis-inducing properties in a cancer cell model, finding that treatment with compounds 5a–e led to apoptotic cell death. [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1186/s13065-018-0462-x) contains supplementary material, which is available to authorized users.
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spelling pubmed-61195542018-09-11 Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol Arumugam, Natarajan Almansour, Abdulrahman I. Kumar, Raju Suresh Al-thamili, Dhaifallah M. Periyasami, Govindasami Periasamy, V. S. Athinarayanan, Jegan Alshatwi, Ali A. Mahalingam, S. M. Menéndez, J. Carlos Chem Cent J Short Report BACKGROUND: Spiropyrrolidine tethered piperidone heterocyclic hybrids were synthesized with complete regio- and stereoselectively in excellent yield via a tandem three-component 1,3-dipolar cycloaddition and subsequent enamine reaction in [bmim]Br. The synthesized compounds were evaluated for their anticancer activity against FaDu hypopharyngeal tumor cells. FINDINGS: Interestingly, most compounds displayed cytotoxicities similar to the standard anticancer agent bleomycin, with two of them (5a and 5g) being slightly more active than the reference drug. CONCLUSION: Synthesized compounds have also been evaluated for their apoptosis-inducing properties in a cancer cell model, finding that treatment with compounds 5a–e led to apoptotic cell death. [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1186/s13065-018-0462-x) contains supplementary material, which is available to authorized users. Springer International Publishing 2018-09-01 /pmc/articles/PMC6119554/ /pubmed/30173362 http://dx.doi.org/10.1186/s13065-018-0462-x Text en © The Author(s) 2018 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.
spellingShingle Short Report
Arumugam, Natarajan
Almansour, Abdulrahman I.
Kumar, Raju Suresh
Al-thamili, Dhaifallah M.
Periyasami, Govindasami
Periasamy, V. S.
Athinarayanan, Jegan
Alshatwi, Ali A.
Mahalingam, S. M.
Menéndez, J. Carlos
Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol
title Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol
title_full Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol
title_fullStr Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol
title_full_unstemmed Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol
title_short Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol
title_sort regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol
topic Short Report
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6119554/
https://www.ncbi.nlm.nih.gov/pubmed/30173362
http://dx.doi.org/10.1186/s13065-018-0462-x
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