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.
Highlights
Indole is one of the most versatile heterocyclic nuclei, identified as a pharmacophore in a large number of natural and synthetic biologically active molecules [1]
We can plausibly assume that, in these conditions, the paraformaldehyde is rapidly converted to is rapidly converted to free formaldehyde and the traces of formic acid produced during prolonged free formaldehyde and the traces of formic acid produced during prolonged heating are rapidly heating are rapidly neutralized by calcium oxide (CaO)
Following the experiment by means of gas chromatography–mass spectrometry chromatography–mass spectrometry (GC–MS) analysis (Figure 1), we observed, from the very (GC–MS) analysis (Figure 1), we observed, from the very beginning of the reaction and only in the beginning of the reaction and only in the presence of CaO, the formation of the indole-1-carbinol 5, presence of CaO, the formation of the indole-1-carbinol 5, which is usually obtained in a strong basic which is usually obtained in a strong basic condition [30,31]
Summary
Indole is one of the most versatile heterocyclic nuclei, identified as a pharmacophore in a large number of natural and synthetic biologically active molecules [1]. Considerable attention is focused on a number of 3,30 -diindolyl methanes (or bis (indolyl) methanes) (3,30 -BIMs), structurally dimers of the dietary component indole-3-carbinol (I3C), with whom they share the same ability to suppress proliferation and induce apoptosis in various cancer cells [3,4,5]. In view of their importance, many methods have been reported for the synthesis of.
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