Late-stage optimization of a tercyclic class of S1P3-sparing, S1P1 receptor agonists

Bioorg Med Chem Lett. 2016 Jan 15;26(2):466-471. doi: 10.1016/j.bmcl.2015.11.090. Epub 2015 Nov 26.

Abstract

Poor solubility and cationic amphiphilic drug-likeness were liabilities identified for a lead series of S1P3-sparing, S1P1 agonists originally developed from a high-throughput screening campaign. This work describes the subsequent optimization of these leads by balancing potency, selectivity, solubility and overall molecular charge. Focused SAR studies revealed favorable structural modifications that, when combined, produced compounds with overall balanced profiles. The low brain exposure observed in rat suggests that these compounds would be best suited for the potential treatment of peripheral autoimmune disorders.

Keywords: Autoimmune; S1P1; S1P3; Solubility.

MeSH terms

  • Animals
  • Brain / metabolism
  • Glutamic Acid / metabolism
  • Hep G2 Cells
  • Humans
  • Hydrogen Bonding
  • Kinetics
  • Oxadiazoles / blood
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / pharmacology*
  • Rats
  • Receptors, Lysosphingolipid / agonists*
  • Solubility
  • Structure-Activity Relationship
  • Thiadiazoles / blood
  • Thiadiazoles / chemical synthesis
  • Thiadiazoles / pharmacology*

Substances

  • Oxadiazoles
  • Receptors, Lysosphingolipid
  • Thiadiazoles
  • Glutamic Acid