Issue 9, 2014

A concise formation of N-substituted 3,4-diarylpyrroles – synthesis and cytotoxic activity

Abstract

A short synthesis of N-substituted 3,4-diarylpyrroles by condensation of a phenacyl halide with a primary amine and a phenylacetaldehyde is reported. The key step is an intramolecular cyclization of an in situ generated enamine onto a ketone. Using differently substituted aromatic reactants and N-(3-aminopropyl)azatricyclodecane as the amine component, the preparation of analogs of the cytotoxic marine alkaloid halitulin could be achieved. The cytotoxicity of some of the compounds obtained by this method was studied, and one of them proved to be a very potent derivative, acting at a nanomolar concentration, in a caspase-independent cell death mechanism.

Graphical abstract: A concise formation of N-substituted 3,4-diarylpyrroles – synthesis and cytotoxic activity

Supplementary files

Article information

Article type
Paper
Submitted
19 Nov 2013
Accepted
13 Jan 2014
First published
14 Jan 2014

Org. Biomol. Chem., 2014,12, 1518-1524

Author version available

A concise formation of N-substituted 3,4-diarylpyrroles – synthesis and cytotoxic activity

M. Egorov, B. Delpech, G. Aubert, T. Cresteil, M. C. Garcia-Alvarez, P. Collin and C. Marazano, Org. Biomol. Chem., 2014, 12, 1518 DOI: 10.1039/C3OB42309C

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