Synthesis and evaluation of a novel E-ring modified alpha-hydroxy keto ether analogue of camptothecin

Bioorg Med Chem. 2002 Jan;10(1):103-10. doi: 10.1016/s0968-0896(01)00252-8.

Abstract

The synthesis of a novel E-ring modified keto ether analogue of camptothecin and homocamptothecin by the cascade radical annulation route is reported. The analogue, Du1441, is an isomer of homocamptothecin, but includes the alpha-hydroxy carbonyl functionality that camptothecin possesses and homocamptothecin lacks. Despite these similarities, the new keto ether analogue is inactive in cell assays, and implications for the structure/activity relationship are discussed.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Camptothecin / analogs & derivatives*
  • Camptothecin / chemical synthesis
  • Camptothecin / pharmacology
  • Chromatography, High Pressure Liquid
  • Ethers / chemistry
  • Humans
  • Molecular Structure
  • Spectrum Analysis
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Ethers
  • Camptothecin