Discovery of Novel Sphingosine-1-Phosphate-1 Receptor Agonists for the Treatment of Multiple Sclerosis

J Med Chem. 2022 Feb 24;65(4):3539-3562. doi: 10.1021/acs.jmedchem.1c01979. Epub 2022 Jan 25.

Abstract

The sphingosine-1-phosphate-1 (S1P1) receptor agonists have great potential for the treatment of multiple sclerosis (MS) because they can inhibit lymphocyte egress through receptor internalization. We designed and synthesized triazole and isoxazoline derivatives to discover a novel S1P1 agonist for MS treatment. Of the two scaffolds, the isoxazoline derivative was determined to have excellent in vitro efficacy and drug-like properties. Among them, compound 21l was found to have superior drug-like properties as well as excellent in vitro efficacies (EC50 = 7.03 nM in β-arrestin recruitment and EC50 = 11.8 nM in internalization). We also confirmed that 21l effectively inhibited lymphocyte egress in the peripheral lymphocyte count test and significantly improved the clinical score in the experimental autoimmune encephalitis MS mouse model.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dogs
  • Drug Design
  • Encephalomyelitis, Autoimmune, Experimental / drug therapy
  • Heart Rate / drug effects
  • Humans
  • Isoxazoles / chemical synthesis
  • Isoxazoles / pharmacokinetics
  • Isoxazoles / pharmacology
  • Lymphocyte Count
  • Lymphocytes / drug effects
  • Male
  • Mice
  • Multiple Sclerosis / drug therapy*
  • Rats
  • Sphingosine-1-Phosphate Receptors / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis
  • Triazoles / pharmacokinetics
  • Triazoles / pharmacology
  • beta-Arrestins / drug effects

Substances

  • Isoxazoles
  • S1PR1 protein, human
  • Sphingosine-1-Phosphate Receptors
  • Triazoles
  • beta-Arrestins