Inhibitors of human mitotic kinesin Eg5: characterization of the 4-phenyl-tetrahydroisoquinoline lead series

Bioorg Med Chem Lett. 2006 Apr 15;16(8):2095-100. doi: 10.1016/j.bmcl.2006.01.056. Epub 2006 Feb 3.

Abstract

In a high-throughput screening effort, a series of tetrahydroisoquinolines was identified as modest inhibitors of human Eg5. A medicinal chemistry optimization effort led to the identification of R-4-(3-hydroxyphenyl)-N,N-7,8-tetramethyl-3,4-dihydroisoquinoline-2(1H)-carboxamide (32a) as a potent inhibitor of human Eg5 (ATPase IC50 104 nM) with good anti-proliferative activity in A2780 cells (IC50 234 nM).

MeSH terms

  • Adenosine Triphosphatases / antagonists & inhibitors
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / pharmacology
  • Kinesins / antagonists & inhibitors*
  • Mitosis / drug effects*
  • Molecular Structure
  • Tetrahydroisoquinolines / chemical synthesis
  • Tetrahydroisoquinolines / pharmacology*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Isoquinolines
  • N-acetyl-1-(4'-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  • Tetrahydroisoquinolines
  • Adenosine Triphosphatases
  • Kinesins