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

作者：Egorov Maxim; Delpech Bernard^*; Aubert Genevieve; Cresteil Thierry; Garcia Alvarez Maria Concepcion; Collin Pascal; Marazano Christian

来源：Organic and Biomolecular Chemistry, 2014, 12(9): 1518-1524.

DOI：10.1039/c3ob42309c

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.

• 出版日期2014