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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MDPI AG
2020-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/23/5581 |
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| author | Raju Suresh Kumar Dhaifallah M. Al-thamili Abdulrahman I. Almansour Natarajan Arumugam Faruq Mohammad |
| author_facet | Raju Suresh Kumar Dhaifallah M. Al-thamili Abdulrahman I. Almansour Natarajan Arumugam Faruq Mohammad |
| author_sort | Raju Suresh Kumar |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-10T14:30:29Z |
| format | Article |
| id | doaj.art-904ed56f06d64dc0ac9550f3865450f6 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T14:30:29Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-904ed56f06d64dc0ac9550f3865450f62023-11-20T22:39:16ZengMDPI AGMolecules1420-30492020-11-012523558110.3390/molecules25235581A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic HybridsRaju Suresh Kumar0Dhaifallah M. Al-thamili1Abdulrahman I. Almansour2Natarajan Arumugam3Faruq Mohammad4Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaWith 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.https://www.mdpi.com/1420-3049/25/23/5581multicomponent reactionfunctionalized spirooxindole-pyrrolidine hybridsanticancer activitycontrolled cell deathapoptosisROS generation |
| spellingShingle | Raju Suresh Kumar Dhaifallah M. Al-thamili Abdulrahman I. Almansour Natarajan Arumugam Faruq Mohammad A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids Molecules multicomponent reaction functionalized spirooxindole-pyrrolidine hybrids anticancer activity controlled cell death apoptosis ROS generation |
| 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 | multicomponent reaction functionalized spirooxindole-pyrrolidine hybrids anticancer activity controlled cell death apoptosis ROS generation |
| url | https://www.mdpi.com/1420-3049/25/23/5581 |
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