Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives
Several new cyano-substituted derivatives with pyrrolo[1,2-<i>a</i>]quinoline and pyrrolo[2,1-<i>a</i>]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 wit...
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MDPI AG
2021-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/7/2066 |
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| author | Maria Cristina Al-Matarneh Roxana-Maria Amărandi Ionel I. Mangalagiu Ramona Danac |
| author_facet | Maria Cristina Al-Matarneh Roxana-Maria Amărandi Ionel I. Mangalagiu Ramona Danac |
| author_sort | Maria Cristina Al-Matarneh |
| collection | DOAJ |
| description | Several new cyano-substituted derivatives with pyrrolo[1,2-<i>a</i>]quinoline and pyrrolo[2,1-<i>a</i>]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 <b>9a</b> 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 <b>9a</b>. |
| first_indexed | 2024-03-10T12:38:13Z |
| format | Article |
| id | doaj.art-f491304d5db347ba9c98c662e00c660c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T12:38:13Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f491304d5db347ba9c98c662e00c660c2023-11-21T14:09:35ZengMDPI AGMolecules1420-30492021-04-01267206610.3390/molecules26072066Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline DerivativesMaria Cristina Al-Matarneh0Roxana-Maria Amărandi1Ionel I. Mangalagiu2Ramona Danac3Department of Chemistry, Faculty of Chemistry, Alexandru Ioan Cuza University of Iași, 11 Carol I, 700506 Iași, RomaniaDepartment of Chemistry, Faculty of Chemistry, Alexandru Ioan Cuza University of Iași, 11 Carol I, 700506 Iași, RomaniaDepartment of Chemistry, Faculty of Chemistry, Alexandru Ioan Cuza University of Iași, 11 Carol I, 700506 Iași, RomaniaDepartment of Chemistry, Faculty of Chemistry, Alexandru Ioan Cuza University of Iași, 11 Carol I, 700506 Iași, RomaniaSeveral new cyano-substituted derivatives with pyrrolo[1,2-<i>a</i>]quinoline and pyrrolo[2,1-<i>a</i>]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 <b>9a</b> 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 <b>9a</b>.https://www.mdpi.com/1420-3049/26/7/20663 + 2 cycloadditionpyrrolo fused (iso)quinolineanticancertubulin polymerization inhibitormolecular docking |
| spellingShingle | Maria Cristina Al-Matarneh Roxana-Maria Amărandi Ionel I. Mangalagiu Ramona Danac Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives Molecules 3 + 2 cycloaddition pyrrolo fused (iso)quinoline anticancer tubulin polymerization inhibitor molecular docking |
| title | Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives |
| title_full | Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives |
| title_fullStr | Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives |
| title_full_unstemmed | Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives |
| title_short | Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives |
| title_sort | synthesis and biological screening of new cyano substituted pyrrole fused iso quinoline derivatives |
| topic | 3 + 2 cycloaddition pyrrolo fused (iso)quinoline anticancer tubulin polymerization inhibitor molecular docking |
| url | https://www.mdpi.com/1420-3049/26/7/2066 |
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