Three-component synthesis, utilization and biological activity of phosphinoyl-functionalized isoindolinones

Popovics-Tóth, Nóra and Rávai, Bettina and Tajti, Ádám and Varga, Bence and Bagi, Péter and Perdih, Franc and Szabó, Pál Tamás and Hackler Jr., László and Puskás, László G. and Bálint, Erika (2021) Three-component synthesis, utilization and biological activity of phosphinoyl-functionalized isoindolinones. ORGANIC & BIOMOLECULAR CHEMISTRY. ISSN 1477-0520

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Abstract

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.

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