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Article

Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives

1
Department of Chemistry, Faculty of Chemistry, Alexandru Ioan Cuza University of Iași, 11 Carol I, 700506 Iași, Romania
2
“Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy, 41A Grigore Ghica Voda Alley, 700487 Iași, Romania
3
TRANSCEND Research Center, Regional Institute of Oncology, 2-4 General Henri Mathias Berthelot Street, 700483 Iași, Romania
*
Authors to whom correspondence should be addressed.
Academic Editor: Vincenzo Piccialli
Molecules 2021, 26(7), 2066; https://doi.org/10.3390/molecules26072066
Received: 7 March 2021 / Revised: 18 March 2021 / Accepted: 1 April 2021 / Published: 3 April 2021
Several new cyano-substituted derivatives with pyrrolo[1,2-a]quinoline and pyrrolo[2,1-a]isoquinoline scaffolds were synthesized by the [3 + 2] cycloaddition of (iso)quinolinium ylides to fumaronitrile. The cycloimmonium ylides reacted in situ as 1,3-dipoles with fumaronitrile to selectively form distinct final compounds, depending on the structure of the (iso)quinolinium salt. Eleven compounds were evaluated for their anticancer activity against a panel of 60 human cancer cell lines. The most potent compound 9a showed a broad spectrum of antiproliferative activity against cancer cell lines representing leukemia, melanoma and cancer of lung, colon, central nervous system, ovary, kidney, breast and prostate cancer. In vitro assays and molecular docking revealed tubulin interaction properties of compound 9a. View Full-Text
Keywords: 3 + 2 cycloaddition; pyrrolo fused (iso)quinoline; anticancer; tubulin polymerization inhibitor; molecular docking 3 + 2 cycloaddition; pyrrolo fused (iso)quinoline; anticancer; tubulin polymerization inhibitor; molecular docking
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MDPI and ACS Style

Al-Matarneh, M.C.; Amărandi, R.-M.; Mangalagiu, I.I.; Danac, R. Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives. Molecules 2021, 26, 2066. https://doi.org/10.3390/molecules26072066

AMA Style

Al-Matarneh MC, Amărandi R-M, Mangalagiu II, Danac R. Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives. Molecules. 2021; 26(7):2066. https://doi.org/10.3390/molecules26072066

Chicago/Turabian Style

Al-Matarneh, Maria C., Roxana-Maria Amărandi, Ionel I. Mangalagiu, and Ramona Danac. 2021. "Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives" Molecules 26, no. 7: 2066. https://doi.org/10.3390/molecules26072066

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