Discovery of novel 4-phenyl-2-(pyrrolidinyl)nicotinamide derivatives as potent Nav1.1 activators

Bioorg Med Chem Lett. 2019 Mar 15;29(6):815-820. doi: 10.1016/j.bmcl.2019.01.023. Epub 2019 Jan 23.

Abstract

The voltage-gated sodium channel, Nav1.1, is predominantly expressed in parvalbumin-positive fast spiking interneurons and has been genetically linked to Dravet syndrome. Starting from a high throughput screening hit isoxazole derivative 5, modifications of 5 via combinations of IonWorks and Q-patch assays successfully identified the nicotinamide derivative 4. Its increasing decay time constant (tau) of Nav1.1 currents at 0.03 μM along with significant selectivity against Nav1.2, Nav1.5, and Nav1.6 and acceptable brain exposure in mice was observed. Compound 4 is a promising Nav1.1 activator that can be used to analyze pathophysiological functions of the Nav1.1 channel towards treating various central nervous system diseases.

Keywords: BBB penetration; Dravet syndrome; Na(v)1.1 activator; Slow current decay of inactivation; Voltage-gated sodium channels.

MeSH terms

  • Animals
  • Blood-Brain Barrier / metabolism
  • CHO Cells
  • Cricetulus
  • Drug Discovery*
  • Mice
  • Molecular Structure
  • NAV1.1 Voltage-Gated Sodium Channel / metabolism
  • Niacinamide / analogs & derivatives*
  • Niacinamide / chemical synthesis
  • Niacinamide / pharmacology*
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry
  • Pyrrolidines / pharmacology*
  • Structure-Activity Relationship
  • Voltage-Gated Sodium Channel Agonists / chemical synthesis
  • Voltage-Gated Sodium Channel Agonists / chemistry
  • Voltage-Gated Sodium Channel Agonists / pharmacology*

Substances

  • NAV1.1 Voltage-Gated Sodium Channel
  • Pyrrolidines
  • Voltage-Gated Sodium Channel Agonists
  • Niacinamide