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A facile atom economic one pot multicomponent synthesis of bioactive spiro-indenoquinoxaline pyrrolizines as potent antioxidant and anti cancer agents

Abstract

An competent and highly discriminating one-pot synthesis of biologically active novel spiro-indenoquinoxaline pyrrolizines accumulating three pharmocophoric cores, heterocyclic quinoline scaffold, pyrrolizines and indeno-quinoxaline in a single molecular framework by means of four-component reaction between ninhydrin, o-phenylenediamine, L-proline and quinolinyl chalcones in methanol via [3+2]cycloaddition. The structures of the compounds were well characterized by FT-IR, NMR, ESI-MS, XRD and elemental analysis. The synthesized compounds were screened for in vitro antioxidant activity using DPPH, nitric oxide, super oxide radical and in vitro cytotoxic activity against MCF-7 and A-549 cancer cell lines and were visualized using Fluorescent microscopic technique. The newly synthesized compounds exhibited excellent antioxidant activity when compared to the standard molecule ie., BHT. In case of cytotoxic activity compounds 5c, 5e, 6c and 6e were found to be admirable activity when compared to standard doxorubicin against MCF-7 and A-549 cancer cells by MTT assay method. From the cell morphology analysis we clearly indicate that induced cell death by apoptosis and necrosis pathway. Molecular docking studies were performed out using EGFR inhibitor to determine the molecular interactions between compounds and proteins.

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Publication details

The article was received on 12 Aug 2017, accepted on 11 Nov 2017 and first published on 14 Nov 2017


Article type: Paper
DOI: 10.1039/C7NJ02993D
Citation: New J. Chem., 2017, Accepted Manuscript
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    A facile atom economic one pot multicomponent synthesis of bioactive spiro-indenoquinoxaline pyrrolizines as potent antioxidant and anti cancer agents

    K. Saravana Mani, W. Kaminsky and S. P. Rajendran, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ02993D

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