Discovery of imidazopyridazines as potent Pim-1/2 kinase inhibitors

Bioorg Med Chem Lett. 2016 Nov 15;26(22):5580-5590. doi: 10.1016/j.bmcl.2016.09.067. Epub 2016 Oct 1.

Abstract

High levels of Pim expression have been implicated in several hematopoietic and solid tumor cancers, suggesting that inhibition of Pim signaling could provide patients with therapeutic benefit. Herein, we describe our progress towards this goal using a screening hit (rac-1) as a starting point. Modification of the indazole ring resulted in the discovery of a series of imidazopyridazine-based Pim inhibitors exemplified by compound 22m, which was found to be a subnanomolar inhibitor of the Pim-1 and Pim-2 isoforms (IC50 values of 0.024nM and 0.095nM, respectively) and to potently inhibit the phosphorylation of BAD in a cell line that expresses high levels of all Pim isoforms, KMS-12-BM (IC50=28nM). Profiling of Pim-1 and Pim-2 expression levels in a panel of multiple myeloma cell lines and correlation of these data with the potency of compound 22m in a proliferation assay suggests that Pim-2 inhibition would be advantageous for this indication.

Keywords: Hematologic cancer; Kinase inhibitor; Multiple myeloma; Oncology; Pim kinase; Proliferation.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Humans
  • Models, Molecular
  • Multiple Myeloma / drug therapy
  • Multiple Myeloma / metabolism
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / pharmacology*
  • Protein Serine-Threonine Kinases / antagonists & inhibitors*
  • Protein Serine-Threonine Kinases / metabolism
  • Proto-Oncogene Proteins / antagonists & inhibitors*
  • Proto-Oncogene Proteins / metabolism
  • Proto-Oncogene Proteins c-pim-1 / antagonists & inhibitors*
  • Proto-Oncogene Proteins c-pim-1 / metabolism
  • Pyridazines / chemistry*
  • Pyridazines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • PIM2 protein, human
  • Protein Kinase Inhibitors
  • Proto-Oncogene Proteins
  • Pyridazines
  • Protein Serine-Threonine Kinases
  • Proto-Oncogene Proteins c-pim-1