Synthesis of organophosphoms derivatives of 2-aminoglucopyranose and their antitumor activities

A series of novel N-[（p-substituted phenyl）dialkoxyphosphoryl]methyl-2-amino-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose 4 were synthesized by the addition reaction of the imines 3 with the phosphites.And through subsequent alcoholysis of compounds 4,new 2-aminoglucopyranose derivatives 5 were obtained.1HNMR and 31P NMR spectra indicated that compounds 4 wre mixtures of diastereoisomers.Two’isomers,4 d’and 4i’,were isolated and purified by recrystalization,respectively.The molecular structure of the isomer 4i’wasdetermined by X-ray diffraction.Preliminary biological tests showed that some of these compounds possess inhib-iting activities agaimt L1 210and HL-60 cells in vitro and S-180 cancer in vivo.

<正> A series of novel N-[（p-substituted phenyl）dialkoxyphosphoryl]methyl-2-amino-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose 4 were synthesized by the addition reaction of the imines 3 with the phosphites.And through subsequent alcoholysis of compounds 4,new 2-aminoglucopyranose derivatives 5 were obtained.1HNMR and31P NMR spectra indicated that compounds 4 wre mixtures of diastereoisomers.Two’isomers,4 d’and 4i’,were isolated and purified by recrystalization,respectively.The molecular structure of the isomer 4i’wasdetermined by X-ray diffraction.Preliminary biological tests showed that some of these compounds possess inhib-iting activities agaimt L1 210and HL-60 cells in vitro and S-180 cancer in vivo.