A new method for the synthesis of 3-oxoisoindolin-1-ylphosphine oxides bearing same
or different substituents on the phosphorus atom is described. The one-pot three-component
reaction of 2-formylbenzoic acid, primary amines and achiral or P-stereogenic secondary
phosphine oxides provided the target compounds under catalyst-free, mild conditions
and for short reaction times. The deoxygenation of a 3-oxoisoindolin-1-ylphosphine
oxide was also studied, and the phosphine obtained could be converted to a sulphide
and to a platinum complex. The crystal structures of a selected phosphine oxide and
the corresponding platinum species were investigated by X-ray diffraction analysis.
The biological activity, such as in vitro cytotoxicity on different cell lines and
antibacterial activity of the 3-oxoisoindolin-1-ylphosphine oxides was also investigated.
Based on the IC50 values obtained, several derivatives showed moderate activity against
the HL-60 cell line and two compounds containing 3,5-dimethylphenyl groups on the
phosphorus atom showed promising activity against Bacillus subtilis bacteria.
