Synthesis and biological activity of O-alkyl-3-N-aminoacyloxymethyl-5-fluoro-2'-deoxyuridine derivatives

Chem Pharm Bull (Tokyo). 1996 Jun;44(6):1196-201. doi: 10.1248/cpb.44.1196.

Abstract

In an attempt to improve the effectiveness of action of 5-fluoro-2'-deoxyuridine (FUdR), various kinds of O-alkylated water-soluble analogues were synthesized. Antitumor activities against sarcoma 180 (solid) were also evaluated. Some compounds exhibited potent activities. In particular, 3'-O-p-chlorobenzyl-3-N-aminoacyloxy-methylester derivatives were effective over a very wide range of dose and gave extremely large therapeutic ratios compared with known 5-fluorouracil (5-FU) derivations.

MeSH terms

  • Animals
  • Antimetabolites, Antineoplastic / chemical synthesis*
  • Antimetabolites, Antineoplastic / pharmacokinetics
  • Antimetabolites, Antineoplastic / pharmacology
  • Chemical Phenomena
  • Chemistry, Physical
  • Deoxyuridine / analogs & derivatives
  • Deoxyuridine / chemical synthesis*
  • Deoxyuridine / pharmacokinetics
  • Deoxyuridine / pharmacology
  • Female
  • Floxuridine / analogs & derivatives*
  • Floxuridine / chemical synthesis
  • Floxuridine / pharmacology
  • Mice
  • Mice, Inbred ICR
  • Sarcoma 180 / drug therapy

Substances

  • Antimetabolites, Antineoplastic
  • Floxuridine
  • Deoxyuridine