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A new four-component reaction involving the Michael addition and the Gewald reaction, leading to diverse biologically active 2-aminothiophenes

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Abstract

The Gewald three-component reaction yielding highly substituted 2-aminothiophene heterocycles has been known for a long time and holds an extraordinary potential in the pharmaceutical industry. Herein, we describe a four-component reaction initiated by the conjugate addition of different indole derivatives to α,β-unsaturated carbonyl compounds. This is followed by an in situ Gewald three-component reaction which results in the formation of a compound containing an indole and a 2-aminothiophene moiety separated by a methylene spacer. We also examined the impact of the use of other nucleophilic components such as pyrrole derivatives on this MG-4CR (Michael–Gewald four component reaction). All these synthesized compounds were tested for anti-proliferative activity and three of them showed activity in the nanomolar range.

Graphical abstract: A new four-component reaction involving the Michael addition and the Gewald reaction, leading to diverse biologically active 2-aminothiophenes

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Publication details

The article was received on 22 Mar 2017, accepted on 09 Apr 2017 and first published on 11 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00707H
Citation: Org. Biomol. Chem., 2017, Advance Article
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    A new four-component reaction involving the Michael addition and the Gewald reaction, leading to diverse biologically active 2-aminothiophenes

    J. Thomas, S. Jana, M. Sonawane, B. Fiey, J. Balzarini, S. Liekens and W. Dehaen, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00707H

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