5031-11-8Relevant academic research and scientific papers
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
Tocco, Graziella,Zedda, Gloria,Casu, Mariano,Simbula, Gabriella,Begala, Michela
, (2017/11/07)
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.
Mild synthetic approach to novel indole-1-carbinols and preliminary evaluation of their cytotoxicity in hepatocarcinoma cells
Zedda, Gloria,Simbula, Gabriella,Begala, Michela,Pibiri, Monica,Floris, Costantino,Casu, Mariano,Casu, Laura,Tocco, Graziella
experimental part, p. 195 - 202 (2012/06/04)
A mild and versatile method for the synthesis of some novel indole-1-carbinols has been developed via one-pot reaction of indoles and paraformaldehyde in the presence of an excess of CaO, MgO, ZnO or TiO 2. The solvent-free reaction provided all the indole derivatives in moderate to good yields and short reaction times. Moreover, the effect of some selected indole-1-carbinols on cell proliferation of the hepatoma cell line FaO was evaluated.
Studies in the Protection of Pyrrole and Indole Derivatives
Dhanak, Dashyant,Reese, Colin B.
, p. 2181 - 2186 (2007/10/02)
Treatment of pyrrole (1a), 2,5-dimethylpyrrole (1b), indole (3a), 2-methylindole (3b), 3-methylindole (3c), 2,3-dimethylindole (3d), 1,2,3,4-tetrahydro-9H-carbazole (5a), 5,6,7,8,9,10-hexahydrocycloheptindole (5b), and 6,7,8,9,10,11-hexahydro-5H-cyclo-octindole (5c) with sodium hydride in tetrahydrofuran, followed by phenyl t-butyl carbonate (8) gives the corresponding N-t-butoxycarbonyl (t-BOC) derivatives in satisfactory yields.By using chlorodimethyl-t-butylsilane instead of (8), N-dimethyl-t-butylsilyl derivatives are obtained, also in satisfactory yields.The use of the 2-(trimethylsilyl)ethoxycarbonyl (TEOC) group for the N-protection of the indole system, and the pivaloyloxymethyl (POM) group for the N-protection of the pyrrole and indole systems is also described.
