Synthesis of new camptothecin analogs with improved antitumor activities

Bioorg Med Chem Lett. 2009 Apr 1;19(7):2018-21. doi: 10.1016/j.bmcl.2009.02.031. Epub 2009 Feb 12.

Abstract

Novel hexacyclic camptothecin analogs containing cyclic amidine, urea, or thiourea moiety were designed and synthesized based on the proposed 3D-structure of the topoisomerase I (Topo I)/DNA/camptothecin ternary complex. The analogs were prepared from 9-nitrocamptothecin via 7,9-diaminocamptothecin derivatives as a key intermediate. Among them, 7c exhibited in vivo antitumor activities superior to CPT-11 in human cancer xenograft models in mice at their maximum tolerated doses though its in vitro antiproliferative activity was comparable to SN-38 against corresponding cell lines.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Camptothecin / analogs & derivatives*
  • Camptothecin / chemical synthesis
  • Camptothecin / chemistry
  • Camptothecin / pharmacology
  • Cell Line, Tumor
  • DNA Topoisomerases, Type I / metabolism
  • Humans
  • Mice
  • Structure-Activity Relationship
  • Topoisomerase I Inhibitors*
  • Transplantation, Heterologous

Substances

  • Antineoplastic Agents
  • CH 0793076
  • Topoisomerase I Inhibitors
  • DNA Topoisomerases, Type I
  • Camptothecin