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A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids

With an aim to develop more effective and affordable anticancer agents possessing a unique mechanism of action, we designed and synthesized derivatives of spirooxindole-pyrrolidine heterocyclic hybrids in good yields through a one-pot three-component (3+2) cycloaddition strategy. The synthesized com...

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Autores principales: Kumar, Raju Suresh, M. Al-thamili, Dhaifallah, Almansour, Abdulrahman I., Arumugam, Natarajan, Mohammad, Faruq
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7730040/
https://www.ncbi.nlm.nih.gov/pubmed/33261115
http://dx.doi.org/10.3390/molecules25235581
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author Kumar, Raju Suresh
M. Al-thamili, Dhaifallah
Almansour, Abdulrahman I.
Arumugam, Natarajan
Mohammad, Faruq
author_facet Kumar, Raju Suresh
M. Al-thamili, Dhaifallah
Almansour, Abdulrahman I.
Arumugam, Natarajan
Mohammad, Faruq
author_sort Kumar, Raju Suresh
collection PubMed
description With an aim to develop more effective and affordable anticancer agents possessing a unique mechanism of action, we designed and synthesized derivatives of spirooxindole-pyrrolidine heterocyclic hybrids in good yields through a one-pot three-component (3+2) cycloaddition strategy. The synthesized compounds were characterized thoroughly for the physicochemical properties by making use of FT-IR, NMR spectroscopy, and mass spectrometry. Further, these compounds have been evaluated for the influence of anticancer activity against HepG2 cells up to 200 µg/mL concentration. The highly active molecular scaffold was tested for the in-depth mechanistic studies, and it was found that the major pathway of cell death is apoptosis which occurs through the induction of reactive oxygen species followed by the involvement of caspases.
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spelling pubmed-77300402020-12-12 A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids Kumar, Raju Suresh M. Al-thamili, Dhaifallah Almansour, Abdulrahman I. Arumugam, Natarajan Mohammad, Faruq Molecules Article With an aim to develop more effective and affordable anticancer agents possessing a unique mechanism of action, we designed and synthesized derivatives of spirooxindole-pyrrolidine heterocyclic hybrids in good yields through a one-pot three-component (3+2) cycloaddition strategy. The synthesized compounds were characterized thoroughly for the physicochemical properties by making use of FT-IR, NMR spectroscopy, and mass spectrometry. Further, these compounds have been evaluated for the influence of anticancer activity against HepG2 cells up to 200 µg/mL concentration. The highly active molecular scaffold was tested for the in-depth mechanistic studies, and it was found that the major pathway of cell death is apoptosis which occurs through the induction of reactive oxygen species followed by the involvement of caspases. MDPI 2020-11-27 /pmc/articles/PMC7730040/ /pubmed/33261115 http://dx.doi.org/10.3390/molecules25235581 Text en © 2020 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
Kumar, Raju Suresh
M. Al-thamili, Dhaifallah
Almansour, Abdulrahman I.
Arumugam, Natarajan
Mohammad, Faruq
A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids
title A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids
title_full A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids
title_fullStr A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids
title_full_unstemmed A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids
title_short A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids
title_sort one-pot three-component synthesis and investigation of the in vitro mechanistic anticancer activity of highly functionalized spirooxindole-pyrrolidine heterocyclic hybrids
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7730040/
https://www.ncbi.nlm.nih.gov/pubmed/33261115
http://dx.doi.org/10.3390/molecules25235581
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