Synthesis of novel antiproliferative hybrid bis-(3-indolyl)methane phosphonate derivatives.

Abstract An efficient synthetic methodology for the preparation of phosphorus substituted bis-(3-indolyl)methane through a double nucleophilic addition of indole derivatives to an in situ generated α-iminophosphonate is reported. In addition, bis-(3-indolyl)methane substrates showed in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell lines A549 (carcinomic human alveolar basal epithelial cell) and SKOV03 (human ovarian carcinoma). Graphical abstract Image 1 Highlights • An efficient synthesis of bis(3-indolyl)methane derivatives is reported. • Phosphorated bis-(3-indolyl)methane derivatives are hybrid substrates. They showed in vitro cytotoxicity against cancer. • Substrates 13j and 12c derived from 5-methylindole show very good IC 50 values of about 0.06 μM. [ABSTRACT FROM AUTHOR]