Design, stereoselective synthesis and anticancer efficacy of a new class of functionalized pyrrolizidine heterocyclic hybrids

Eight new functionalized spirooxindole-pyrrolizidine heterocyclic hybrids has been obtained from N-pyridinylmethyl-bisarylmethylidene-pyridinones, Isatin and L-Proline by a multi-component cycloaddition reaction. Such synthesized derivatives are being characterized systematically with the aid of ins...

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Bibliographic Details
Published in:Journal of King Saud University. Science 2024-01, Vol.36 (1), p.103009, Article 103009
Main Authors: Kumar, Raju Suresh, Al-thamili, Dhaifallah M., Ibrahim Al-Shemaimari, Khloud, Mohammad, Faruq, Altaf, Mohamad, Ayub, Rashid
Format: Article
Language:English
Subjects:
Anticancer activity
Apoptosis
Caspase-3 activity
Cycloaddition reaction
ROS generation
Spirooxindole-pyrrolizidines
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Summary:Eight new functionalized spirooxindole-pyrrolizidine heterocyclic hybrids has been obtained from N-pyridinylmethyl-bisarylmethylidene-pyridinones, Isatin and L-Proline by a multi-component cycloaddition reaction. Such synthesized derivatives are being characterized systematically with the aid of instrumental facilities like FT-IR, NMR spectroscopy, and Mass spectrometry. Following this, all the compounds are tested for the anticancer potentials in vitro using HepG2 cells (cancer cells). The compound with no substitution on the aryl rings (phenyl rings), displayed the highest activity among the spirooxindole-pyrrolizidines. Further the most active heterocyclic hybrids are verified for toxicity effects against L929 cells (non-cancer cells; at 200 µg/mL for 24 h). Finally, the cell viability losses for these most active compounds (at its IC50 value) are addressed by assaying the activity of free radicals, apoptosis, and caspases.
ISSN:1018-3647
DOI:10.1016/j.jksus.2023.103009