The effect of protic electron donor aromatic substituents on ferrocenic and [3]ferrocenophanic anilines and anilides: Some aspects of structure–activity relationship studies on organometallic compounds with strong antiproliferative effects

• Strongly cytotoxic ([3]ferrocenophan-1-ylidenemethylene)dianiline was prepared.
• Ferrocenophane compounds derived from Michler's ketone were synthesized.
• N-Acylation and N-methylation decreases activity of dianilines.
• Intramolecular electron transfer process is observed in nitrogenous derivatives.
• Aniline oxidation is influenced by the nature of organometallic moiety.

A new family of nitrogenous derivatives is synthesized, characterized and evaluated for the investigation of the impact of some structural motifs such as functionalization and conjugation on the antiproliferative activity of ferrocenic complexes against cancer cells. These compounds are 4,4′-([3]ferrocenophan-1-ylidenemethylene)dianilides and tetramethylated dianilines derived from Michler's ketone. An alternative McMurry direct heterocoupling method for 4,4′-([3]ferrocenophan-1-ylidenemethylene)dianiline synthesis is described and electrochemical studies are also discussed.

Ferrocenic and [3]ferrocenophanic anilines and anilides have been synthesized and evaluated against triple negative MBA-MB-231 breast cancer cells. Electrochemical studies were discussed.Figure optionsDownload as PowerPoint slide