Preparation And Characterization Of Phospholanes And Phospha Sugars As Novel Anti-Cancer Agents

Abstract

Diastereo isomeric erythro and threo forms of 2,3-epoxy-1-phenylphospholane 1-oxides were synthesized from threo and erythro forms of 2-bromo-3-hydroxy-1-phenylphospholane 1-oxides being prepared from 1-phenyl-2-phospholene 1-oxide. Alternatively, the epoxides were also prepared by the epoxidation of the 2-phospholene with peroxides such as sodium peroxide and hydrogen peroxide. The reactivity and regioselectivity for the reaction of erythro and threo forms of the 2,3-epoxides with nucleophiles were investigated by using amines, and the reaction afforded 2-amino-3-hydroxy-1-phenylphospholane 1-oxides, which correspond to phospha sugar N-glycosides. 2,3-Dibromo-3-methyl-1-phenylphospholane 1-oxides were first prepared from 3-methyl-1-phenyl-2-phospholene 1-oxide. The prepared phospholanes or phospha sugars were biologically qualified by MTT (3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium bromide) in vitro method to find that some of these phosphorus heterocycles or phospha sugars have quite efficient anti-cancer activity for leukemia cells in manners of (i) wide spectra, (ii) high activities, and (iii) high specificities.