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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,...

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Detalles Bibliográficos
Autores principales: 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
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
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
Descripción
Sumario: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.