Preparation and biological evaluation of some 1,2-O-isopropylidene-D-hexofuranose esters

Carbohydr Res. 2006 Mar 20;341(4):538-44. doi: 10.1016/j.carres.2005.12.007. Epub 2006 Jan 17.

Abstract

The synthesis and biological evaluation of some new glycose esters bearing the 1,2-O-isopropylidene-d-hexofuranose functionality and belonging to the 3-O-acyl-d-allose and 6-O-acyl-d-glucose series are reported. When the results concerning cell growth inhibition are compared, it appears that the 6-O-acyl-d-glucose derivatives are more active than the 3-O-acyl-d-allose compounds. Within both 6-O-acyl-d-glucose and 3-O-acyl-d-allose derivatives, butyric esters displayed the highest inhibitory effects. Inhibition of cell growth is not associated with high induction levels of erythroid differentiation, despite the fact that pivaloates induce erythroid differentiation to an extent similar to that exhibited by previously reported molecules [Bioorg. Med. Chem. Lett.1999, 9, 3153-3158].

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemical synthesis*
  • Acetals / pharmacology*
  • Alkenes / chemical synthesis
  • Alkenes / chemistry*
  • Alkenes / pharmacology
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Carbohydrate Conformation
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • Esters / chemical synthesis
  • Esters / chemistry*
  • Esters / pharmacology*
  • Furans / chemical synthesis
  • Furans / chemistry*
  • Furans / pharmacology
  • Hexoses / chemical synthesis
  • Hexoses / chemistry*
  • Hexoses / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • K562 Cells

Substances

  • Acetals
  • Alkenes
  • Antineoplastic Agents
  • Esters
  • Furans
  • Hexoses
  • propylene