Novel Biologically Active 1,3,2-Oxazaphosphinane Derivatives

Abstract

The facile synthetic approaches to a wide range of potentially biologically active compounds bearing the cyclic 1,3,2-oxazaphosphinane moiety as a “cell transport” and the residues of formic, acetic, and amino acids or 3,5-bis(benzylidene)piperidone framework have been developed. The methods are based on the Arbuzov reaction of preformed cyclic P(III) esters with chloroacetic or chloroformic acid esters, where the nature of the reactants influences the ratio of cyclic and linear products, cyclizations of susbstituted dichlorophosphoryl compounds with aminopropanols, or amination of P-isothiocyanates.

Keywords:

• Arbuzov reaction
• 3,5-bis(benzylidene)piperidones
• 3,5-bis(benzylidene)piperidone thioureas
• 1,3,2-oxazaphosphinane
• phosphorylacetic acid
• phosphorylformic acid

Acknowledgments

This work was supported by the Program of Chemistry and Material Science Division of RAS. The authors are grateful to Dr. E. Yu. Rybalkina (Institute of Carcinogenesis, N. N. Blokhin Russian Cancer Research Center, Russian Academy of Medical Sciences) for testing the antitumor properties of the compounds.