Synthesis and antiproliferative activity of (2R,3R)-disubstituted tetrahydropyrans

Bioorg Med Chem Lett. 2006 Dec 1;16(23):6135-8. doi: 10.1016/j.bmcl.2006.08.094. Epub 2006 Sep 6.

Abstract

In this study, we synthesized a series of enantiomerically pure (2R,3R)-disubstituted tetrahydropyrans with diverse functional groups. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780 (ovarian cancer), SW1573 (non-small cell lung cancer), and WiDr (colon cancer). Overall, the results show the relevance for antiproliferative activity of the alpha,beta-unsaturated ester side chain at position 2 of the THP ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Humans
  • Hydrogen / chemistry*
  • Hydrophobic and Hydrophilic Interactions
  • Molecular Structure
  • Pyrans / chemical synthesis
  • Pyrans / chemistry*
  • Pyrans / pharmacology*
  • Structure-Activity Relationship

Substances

  • Pyrans
  • Hydrogen