Synthesis and anticonvulsant activity of a new class of 2-[(arylalky)amino]alkanamide derivatives

J Med Chem. 1998 Feb 12;41(4):579-90. doi: 10.1021/jm970599m.

Abstract

Although most epilepsies are adequately treated by conventional antiepileptic therapy, there remains an unfulfilled need for safer and more effective anticonvulsant agents. Starting from milacemide, a weak anticonvulsant, and trying to elucidate its mechanism of action, we discovered a structurally novel class of potent and preclinically safe anticonvulsants. Here we report the structure-activity relationship (SAR) study within this series of compounds. Different parts of the structural lead 2-[[4-(3-chlorobenzoxy)benzyl]amino]acetamide (6) were thus varied (Figure 1), and many potent anticonvulsants were found. As an outcome of this study, 57 ((S)-2-[[4-(3-fluorobenzoxy)benzyl]amino]propanamide methanesulfonate, PNU-151774E) emerged as a promising candidate for further development for its potent anticonvulsant activity and outstanding therapeutic indexes (TIs) in different animal tests.

MeSH terms

  • Alanine / analogs & derivatives
  • Alanine / chemical synthesis*
  • Alanine / chemistry
  • Alanine / pharmacology
  • Animals
  • Anticonvulsants / chemical synthesis*
  • Anticonvulsants / chemistry
  • Anticonvulsants / pharmacology
  • Benzylamines / chemical synthesis*
  • Benzylamines / chemistry
  • Benzylamines / pharmacology
  • Bicuculline
  • Drug Design
  • Electroshock
  • Indicators and Reagents
  • Male
  • Mice
  • Mice, Inbred ICR
  • Models, Molecular
  • Molecular Structure
  • Motor Activity / drug effects
  • Picrotoxin
  • Postural Balance / drug effects
  • Postural Balance / physiology
  • Rats
  • Rats, Inbred Strains
  • Seizures / chemically induced
  • Seizures / etiology
  • Seizures / prevention & control*
  • Structure-Activity Relationship
  • Strychnine

Substances

  • Anticonvulsants
  • Benzylamines
  • Indicators and Reagents
  • Picrotoxin
  • safinamide
  • Strychnine
  • Alanine
  • Bicuculline