Synthesis and Anticonvulsant Activity of Some N‐Phenyl‐2‐phtalimidoethanesulfonamide Derivatives

Abstract

In this study, inspired by the structures of the taltrimide, 2-phthalimidoethanesulphonamide, and the anilide pharmacophore known to be synthetically produced anticonvulsant compounds, fifteen N-phenyl-2-phtalimidoethanesulfonamide derivatives bearing substituents with diverse electronic and hydrophobic features on N-phenyl ring were synthesized. The structural confirmation of the title compounds was achieved by interpretation of spectral and analytical data. The anticonvulsant activity of the title compounds was determined against maximal electroshock seizure in mice at a dose level of 100 mg/kg. The preliminary screening results indicated that the exchange of the N-isopropyl moiety for an N-phenyl ring in the taltrimide molecule abolished the anticonvulsant activity. However, introducing certain substituents, such as nitro, methyl, and chloro, into the N-phenyl ring lead to more active compounds in comparison to the unsubstituted derivatives.

Recent Progress in Anticonvulsant Drug Research: Strategies for Anticonvulsant Drug Development and Applications of Antiepileptic Drugs for Non-Epileptic Central Nervous System Disorders

“…Fifteen N-phenyl-2-phtalimidoethanesulfonamide derivatives (63) which possessed substituents with different electronic and hydrophobic properties on N-phenyl ring were synthesized [209]. Anticonvulsant activity of these sulphonamide derivatives was tested only against MES seizure at only one dose level (100 mg/kg) in mice since taltrimide and anticonvulsant anilides were more active in MES test.…”

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

“…Compound B was then reacted with corresponding aniline derivatives to yield the title compounds 1-10. The detailed synthetic procedure and their characterizations by 1 H NMR, IR, mass spectral data and elemental analysis were reported in our previous study (23).…”

“…All solvents used in this study were of analytical grade. Compound A and B was prepared as described previously (13,23). 1 H NMR spectra were scanned on a Varian AS 400 Mercury Plus NMR spectrometer using DMSO-d 6 as solvent.…”

“…The title compounds 1-10 were reported in our previous study whereas 11-15 were reported in different studies as intermediates of diverse compounds (12,13,23). None of the compounds have been tested for their antimicrobial activity before though taurine derivatives known to posses antimicrobial activity (12,24).…”

Synthesis and degradation study of novel polyamides derived from a biologically active aromatic diacid monomer 5-(2-phthalimidoethanesulfonamido) isophthalic acid

“…The reports on the anticonvulsant activity of taurine in animal models prompted the synthesis and anticonvulsant evaluation of taurine-containing compounds [13][14][15][16][17][18].…”