Kinesin spindle protein (KSP) inhibitors. Part 6: Design and synthesis of 3,5-diaryl-4,5-dihydropyrazole amides as potent inhibitors of the mitotic kinesin KSP

Bioorg Med Chem Lett. 2007 Oct 1;17(19):5390-5. doi: 10.1016/j.bmcl.2007.07.046. Epub 2007 Aug 6.

Abstract

3,5-diaryl-4,5-dihydropyrazoles were discovered to be potent KSP inhibitors with excellent in vivo potency. These enzyme inhibitors possess desirable physical properties that can be readily modified by incorporation of a weakly basic amine. Careful adjustment of amine basicity was essential for preserving cellular potency in a multidrug resistant cell line while maintaining good aqueous solubility.

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / antagonists & inhibitors
  • Amides / chemical synthesis*
  • Amides / pharmacology*
  • Antimitotic Agents / chemical synthesis*
  • Antimitotic Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Chemical Phenomena
  • Chemistry, Physical
  • Drug Design
  • Drug Resistance, Neoplasm
  • Genes, MDR / drug effects
  • Humans
  • Indicators and Reagents
  • Kinesins / antagonists & inhibitors*
  • Mitosis / drug effects*
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacology*
  • Solubility
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Amides
  • Antimitotic Agents
  • Antineoplastic Agents
  • Indicators and Reagents
  • KIF11 protein, human
  • Pyrazoles
  • Kinesins