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Molecules 2017, 22(10), 1747; doi:10.3390/molecules22101747

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

1
Department of Life and Environmental Sciences, Unit of Drug Sciences, University of Cagliari, via Ospedale 72, 09124 Cagliari, Italy
2
Merck Millipore, 39 Route Industrielle de la Hardt, 67120 Molsheim, France
3
Department of Physics, University of Cagliari, 09042 Monserrato CA, Italy
4
Department of Biomedical Science, Oncology and Molecular Pathology Unit, University of Cagliari, 09124 Cagliari, Italy
These authors equally contributed to the work.
*
Author to whom correspondence should be addressed.
Received: 14 September 2017 / Accepted: 13 October 2017 / Published: 17 October 2017
(This article belongs to the Special Issue The Biomedical Importance of Indoles and Their Derivatives)
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Abstract

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. View Full-Text
Keywords: solvent-free reaction; 1-[1-(1H-indol-3-yl) alkyl]-1H-indoles; hepatocarcinoma; cytotoxicity solvent-free reaction; 1-[1-(1H-indol-3-yl) alkyl]-1H-indoles; hepatocarcinoma; cytotoxicity
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Tocco, G.; Zedda, G.; Casu, M.; Simbula, G.; Begala, M. 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 2017, 22, 1747.

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