Solvent-Free Addition of Indole to Aldehydes: Unexpected Synthesis of Novel 1-[1-(1H-Indol-3-yl) Alkyl]-1H-Indoles and Preliminary Evaluation of Their Cytotoxicity in Hepatocarcinoma Cells
New 1-[1-(1H-indol-3-yl) alkyl]-1H-indoles, surprisingly, have been obtained from the addition of indole to a variety of aldehydes under neat conditions. CaO, present in excess, was fundamental for carrying out the reaction with paraformaldehyde. Under the same reaction conditions, aromatic and hete...
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| Format: | Article |
| Language: | English |
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MDPI AG
2017-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/10/1747 |
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| author | Graziella Tocco Gloria Zedda Mariano Casu Gabriella Simbula Michela Begala |
| author_facet | Graziella Tocco Gloria Zedda Mariano Casu Gabriella Simbula Michela Begala |
| author_sort | Graziella Tocco |
| collection | DOAJ |
| description | New 1-[1-(1H-indol-3-yl) alkyl]-1H-indoles, surprisingly, have been obtained from the addition of indole to a variety of aldehydes under neat conditions. CaO, present in excess, was fundamental for carrying out the reaction with paraformaldehyde. Under the same reaction conditions, aromatic and heteroaromatic aldehydes afforded only classical bis (indolyl) aryl indoles. In this paper, the role of CaO, together with the regiochemistry and the mechanism of the reaction, are discussed in detail. The effect of some selected 3,3′- and 1,3′-diindolyl methane derivatives on cell proliferation of the hepatoma cell line FaO was also evaluated. |
| first_indexed | 2024-12-11T22:47:45Z |
| format | Article |
| id | doaj.art-b21ae6c2a64c4260950cdfd4f0742ad7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T22:47:45Z |
| publishDate | 2017-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b21ae6c2a64c4260950cdfd4f0742ad72022-12-22T00:47:34ZengMDPI AGMolecules1420-30492017-10-012210174710.3390/molecules22101747molecules22101747Solvent-Free Addition of Indole to Aldehydes: Unexpected Synthesis of Novel 1-[1-(1H-Indol-3-yl) Alkyl]-1H-Indoles and Preliminary Evaluation of Their Cytotoxicity in Hepatocarcinoma CellsGraziella Tocco0Gloria Zedda1Mariano Casu2Gabriella Simbula3Michela Begala4Department of Life and Environmental Sciences, Unit of Drug Sciences, University of Cagliari, via Ospedale 72, 09124 Cagliari, ItalyMerck Millipore, 39 Route Industrielle de la Hardt, 67120 Molsheim, FranceDepartment of Physics, University of Cagliari, 09042 Monserrato CA, ItalyDepartment of Biomedical Science, Oncology and Molecular Pathology Unit, University of Cagliari, 09124 Cagliari, ItalyDepartment of Life and Environmental Sciences, Unit of Drug Sciences, University of Cagliari, via Ospedale 72, 09124 Cagliari, ItalyNew 1-[1-(1H-indol-3-yl) alkyl]-1H-indoles, surprisingly, have been obtained from the addition of indole to a variety of aldehydes under neat conditions. CaO, present in excess, was fundamental for carrying out the reaction with paraformaldehyde. Under the same reaction conditions, aromatic and heteroaromatic aldehydes afforded only classical bis (indolyl) aryl indoles. In this paper, the role of CaO, together with the regiochemistry and the mechanism of the reaction, are discussed in detail. The effect of some selected 3,3′- and 1,3′-diindolyl methane derivatives on cell proliferation of the hepatoma cell line FaO was also evaluated.https://www.mdpi.com/1420-3049/22/10/1747solvent-free reaction1-[1-(1H-indol-3-yl) alkyl]-1H-indoleshepatocarcinomacytotoxicity |
| spellingShingle | Graziella Tocco Gloria Zedda Mariano Casu Gabriella Simbula Michela Begala Solvent-Free Addition of Indole to Aldehydes: Unexpected Synthesis of Novel 1-[1-(1H-Indol-3-yl) Alkyl]-1H-Indoles and Preliminary Evaluation of Their Cytotoxicity in Hepatocarcinoma Cells Molecules solvent-free reaction 1-[1-(1H-indol-3-yl) alkyl]-1H-indoles hepatocarcinoma cytotoxicity |
| title | Solvent-Free Addition of Indole to Aldehydes: Unexpected Synthesis of Novel 1-[1-(1H-Indol-3-yl) Alkyl]-1H-Indoles and Preliminary Evaluation of Their Cytotoxicity in Hepatocarcinoma Cells |
| title_full | Solvent-Free Addition of Indole to Aldehydes: Unexpected Synthesis of Novel 1-[1-(1H-Indol-3-yl) Alkyl]-1H-Indoles and Preliminary Evaluation of Their Cytotoxicity in Hepatocarcinoma Cells |
| title_fullStr | Solvent-Free Addition of Indole to Aldehydes: Unexpected Synthesis of Novel 1-[1-(1H-Indol-3-yl) Alkyl]-1H-Indoles and Preliminary Evaluation of Their Cytotoxicity in Hepatocarcinoma Cells |
| title_full_unstemmed | Solvent-Free Addition of Indole to Aldehydes: Unexpected Synthesis of Novel 1-[1-(1H-Indol-3-yl) Alkyl]-1H-Indoles and Preliminary Evaluation of Their Cytotoxicity in Hepatocarcinoma Cells |
| title_short | Solvent-Free Addition of Indole to Aldehydes: Unexpected Synthesis of Novel 1-[1-(1H-Indol-3-yl) Alkyl]-1H-Indoles and Preliminary Evaluation of Their Cytotoxicity in Hepatocarcinoma Cells |
| title_sort | solvent free addition of indole to aldehydes unexpected synthesis of novel 1 1 1h indol 3 yl alkyl 1h indoles and preliminary evaluation of their cytotoxicity in hepatocarcinoma cells |
| topic | solvent-free reaction 1-[1-(1H-indol-3-yl) alkyl]-1H-indoles hepatocarcinoma cytotoxicity |
| url | https://www.mdpi.com/1420-3049/22/10/1747 |
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