Design and Synthesis of Selurampanel, a Novel Orally Active and Competitive AMPA Receptor Antagonist

ChemMedChem. 2017 Feb 3;12(3):197-201. doi: 10.1002/cmdc.201600467. Epub 2016 Nov 15.

Abstract

A series of potent quinazolinedione sulfonamide antagonists of the α-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptor were designed and synthesized. The structure-activity relationships (SAR) and in vivo activity of the series were investigated. In particular, compound 1 S (selurampanel; N-[7-isopropyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1H-quinazolin-3-yl]methanesulfonamide) has shown excellent oral potency against maximal electroshock seizure (MES)-induced generalized tonic-clonic seizures in rodents as well as significant activity in patients suffering from various forms of epilepsy. The X-ray crystal structure of selurampanel bound to the AMPA receptor hGluA was also obtained.

Keywords: AMPA; antagonists; epilepsy; glutamate; quinazolinediones; selurampanel.

MeSH terms

  • Administration, Oral
  • Animals
  • Binding Sites
  • Binding, Competitive
  • Crystallography, X-Ray
  • Disease Models, Animal
  • Drug Design*
  • Electroshock
  • Mice
  • Molecular Dynamics Simulation
  • Protein Structure, Tertiary
  • Quinazolinones / administration & dosage
  • Quinazolinones / chemical synthesis
  • Quinazolinones / chemistry*
  • Quinazolinones / metabolism
  • Receptors, AMPA / antagonists & inhibitors*
  • Receptors, AMPA / metabolism
  • Seizures / drug therapy
  • Structure-Activity Relationship
  • Sulfonamides / administration & dosage
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry
  • Sulfonamides / metabolism

Substances

  • Quinazolinones
  • Receptors, AMPA
  • Sulfonamides
  • selurampanel