Environmentally friendly synthesis and computational studies of novel class of acridinedione integrated spirothiopyrrolizidines/indolizidines

An efficient and environmentally benign synthesis of a new class of acridinedione embedded spirooxindolo/acenaphthenothiopyrrolizidines and spirooxindolo/acenathenoindolizidines has been synthesized in good to excellent yields employing ionic liquid accelerated one-pot [3 + 2]-cycloaddition strategy...

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Published in:Green processing and synthesis 2023-07, Vol.12 (1), p.149-83
Main Authors: Raju, Rajesh, Raghunathan, Raghavachary, Arumugam, Natarajan, Almansour, Abdulrahman I., Kumar, Raju Suresh, Vivekanand, P. A., Ebenezer, Cheriyan, Solomon, Rajadurai Vijay, Perumal, Karthikeyan
Format: Article
Language:English
Subjects:
1,3-dipolar cycloaddition
acridinedione
Chemical bonds
Chemical synthesis
COVID-19
Cycloaddition
Dipoles
ecofriendly green protocol
Ionic liquids
Ions
Molecular docking
spirooxindolo/acenathenoindolizidines
spirooxindolo/acenathenothiopyrrolidines
Substrates
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Summary:An efficient and environmentally benign synthesis of a new class of acridinedione embedded spirooxindolo/acenaphthenothiopyrrolizidines and spirooxindolo/acenathenoindolizidines has been synthesized in good to excellent yields employing ionic liquid accelerated one-pot [3 + 2]-cycloaddition strategy. The pre-requisite starting substrates, -acryloyl acridinediones were prepared from dimedone in three good yielding steps, while the 1,3-dipole was derived from isatin/acenaphthenequinone and thiazolidine-4-carboxylc acid/ -pipecolinic acid via decarboxylative condensation. The cycloadduct possesses three stereogenic carbons, one of which is a spiro carbon through the formation of two C–C and one C–N bonds in one-pot synthetic transformation. Geometrical parameters of the synthesized compounds were calculated using the B3LYP/6-311g(d,p) level of theory. The activity of these molecules was evaluated against main protease of COVID-19 to screen them for their inhibitor efficiency. In order to get a broad understanding of the interactions of these synthesized ligands, a detailed molecular docking analysis was performed. Molecular docking analysis shows that compound has the highest binding affinity toward the protein. The compound can be a potential candidate for the treatment of COVID-19.
ISSN:2191-9550
2191-9542
2191-9550
DOI:10.1515/gps-2023-0036