Recent progress in synthesis of oxazaphosphinanes and their biological applications: a review

Abstract

The oxazaphosphinane represent a novel chemical class of synthetic anticancer agents. They exhibit strong activity against a broad range of human cancers and was first discovered in 1958. The oxazaphosphinane ring plays the role of a "carrier" of a pharmacophoric group to a cell through cell membranes. Oxazaphosphinanes belong to a wide class of organophosphorus compounds and contain an N-P-O or N-C-P O group responsible for their antitumor properties. Thus, they have prompted many pharmaceutical companies to devote resources to this area of investigation. Oxazaphosphinanes can be formally derived fromo-hydroxyaniline, aminoalcohol, bromo-propylaminophosphonate, 2-amino-3-hydroxy-1,4-naphthoquinone, benzylideneamino-2-phenylethanol, oxazolidine, 2-arylideneaminophenols, aminopropanol and dichlorophosphorylisocyanate. The aim of this paper is to review the generalization of the collected data about the synthesis of oxazaphosphinane derivatives, their chemical reactivity and their biological activities. Selected recent syntheses and basic reactions of organic phosphorus chemistry and the synthesis of biologically active organophosphorus compounds are discussed in this review.

Graphical abstract

Keywords:

• Oxazaphosphinanes
• synthetic methodologies
• chemical reactivity
• biological applications

Disclosure statement

There are no conflicts to declare.

Additional information

Funding

This work was supported financially by the General Directorate for Scientific Research and Technological Development (DG-RSDT), Algerian Ministry of Scientific Research, Applied Organic Chemistry Laboratory (FNR 2000).