ArticleJournal of medicinal chemistry2010
Synthesis and anticonvulsant activities of (R)-N-(4'-substituted)benzyl 2-acetamido-3-methoxypropionamides.
Article in Journal of medicinal chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Quinoline Quest: Kynurenic Acid Strategies for Next-Generation Therapeutics via Rational Drug Design.Pharmaceuticals (Basel, Switzerland) · 2025Review
- 6 Hz Active Anticonvulsant Fluorinated N-Benzamide Enaminones and Their Inhibitory Neuronal Activity.International journal of environmental research and public health · 2018Article
- Chimeric derivatives of functionalized amino acids and α-aminoamides: compounds with anticonvulsant activity in seizure models and inhibitory actions on central, peripheral, and cardiac isoforms of voltage-gated sodium channels.Bioorganic & medicinal chemistry · 2015Article
- Chimeric agents derived from the functionalized amino acid, lacosamide, and the α-aminoamide, safinamide: evaluation of their inhibitory actions on voltage-gated sodium channels, and antiseizure and antinociception activities and comparison with lacosamide and safinamide.ACS chemical neuroscience · 2015Article
- Allosteric Modulation of GABAA Receptors by an Anilino Enaminone in an Olfactory Center of the Mouse Brain.Pharmaceuticals (Basel, Switzerland) · 2014Review
- Substituted N-(biphenyl-4'-yl)methyl (R)-2-acetamido-3-methoxypropionamides: potent anticonvulsants that affect frequency (use) dependence and slow inactivation of sodium channels.Journal of medicinal chemistry · 2014Article
- (Biphenyl-4-yl)methylammonium chlorides: potent anticonvulsants that modulate Na+ currents.Journal of medicinal chemistry · 2013Article
- Discovery of lacosamide affinity bait agents that exhibit potent voltage-gated sodium channel blocking properties.ACS chemical neuroscience · 2013Article
- Identification of the benzyloxyphenyl pharmacophore: a structural unit that promotes sodium channel slow inactivation.ACS chemical neuroscience · 2012Article
- Defining the structural parameters that confer anticonvulsant activity by the site-by-site modification of (R)-N'-benzyl 2-amino-3-methylbutanamide.Journal of medicinal chemistry · 2011Article
- Merging Structural Motifs of Functionalized Amino Acids and α-Aminoamides Results in Novel Anticonvulsant Compounds with Significant Effects on Slow and Fast Inactivation of Voltage-gated Sodium Channels and in the Treatment of Neuropathic Pain.ACS chemical neuroscience · 2011Article
- Development and characterization of novel derivatives of the antiepileptic drug lacosamide that exhibit far greater enhancement in slow inactivation of voltage-gated sodium channels.ACS chemical neuroscience · 2011Article
- The structure-activity relationship of the 3-oxy site in the anticonvulsant (R)-N-benzyl 2-acetamido-3-methoxypropionamide.Journal of medicinal chemistry · 2010Article
- Merging the structural motifs of functionalized amino acids and alpha-aminoamides: compounds with significant anticonvulsant activities.Journal of medicinal chemistry · 2010Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
The structure-activity relationship (SAR) for the N-benzyl group in the clinical antiepileptic agent (R)-lacosamide [(R)-N-benzyl 2-acetamido-3-methoxypropionamide, (R)-3] has been explored. Forty-three compounds were prepared and then evaluated at the National Institute of Neurological Disorders and Stroke Anticonvulsant Screening Program for seizure protection in the maximal electroshock (MES) and subcutaneous Metrazol models. Comparing activities for two series of substituted aryl regioisomers (2', 3', 4') showed that 4'-modified derivatives had the highest activity. Significantly, structural latitude existed at the 4'-site. The SAR indicated that nonbulky 4'-substituted (R)-3 derivatives exhibited superb activity, independent of their electronic properties. Activities in the MES test of several compounds were comparable with or exceeded that of (R)-3 and surpassed the activities observed for the traditional antiepileptic agents phenytoin, phenobarbital, and valproate.
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Registered trials
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