Synthesis and cytotoxic activity of new 9-substituted camptothecins

Bioorg Med Chem Lett. 2008 May 1;18(9):2781-7. doi: 10.1016/j.bmcl.2008.04.016. Epub 2008 Apr 10.

Abstract

A series of novel 9-substituted camptothecins derived from 9-formylcamptothecin were synthesized. The aldehyde was obtained from 10-hydroxycamptothecin or, better, by total synthesis. The compounds showed antiproliferative activity higher than that of the reference compound topotecan. Modelling suggested the possibility of a favourable interaction of small and polar 9-substituents with the topoisomerase I-DNA complex, which is consistent with the higher activity of these derivatives with respect to the corresponding 7-substituted camptothecins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Camptothecin / analogs & derivatives
  • Camptothecin / chemical synthesis
  • Camptothecin / pharmacology*
  • Cell Survival / drug effects
  • DNA Topoisomerases, Type I / metabolism
  • Drug Screening Assays, Antitumor
  • Humans
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • DNA Topoisomerases, Type I
  • Camptothecin