A new generation of N-aryl-N'-(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and beta-tubulin alkylation kinetics

J Med Chem. 2003 Nov 6;46(23):5055-63. doi: 10.1021/jm030908a.

Abstract

New N-aryl-N'-2-chloroethylureas (CEUs) with enhanced cytotoxicity were developed as antimitotic agents potentially useful in cancer chemotherapy. Highly potent CEUs were obtained by introduction of a branched alkylating chain, the N'-(1-methyl-2-chloro)ethyl group. Their cytotoxic activity was enantio-dependent and induced through specific alkylation of beta-tubulin, leading to microtubule disruption and mitotic arrest. Overall, the structural modifications of the CEUs described here significantly improved their kinetics of beta-tubulin alkylation. In this new series, CEUs 16a and 18a displayed particularly enhanced antiproliferative activity related to a faster reaction with beta-tubulin and merit further investigation as potential antitumor agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Cell Line
  • Cell Line, Tumor
  • Cricetinae
  • Drug Screening Assays, Antitumor
  • Humans
  • Kinetics
  • Mice
  • Microtubules / drug effects*
  • Phenylurea Compounds / chemical synthesis*
  • Phenylurea Compounds / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tubulin / metabolism*
  • Urea / analogs & derivatives*
  • Urea / chemical synthesis*
  • Urea / pharmacology

Substances

  • Antineoplastic Agents
  • N-(4-isopropyl)phenyl-N'-(1-methyl-2-chloro)ethylurea
  • Phenylurea Compounds
  • Tubulin
  • Urea