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.

• Authors: Ozlem Akgul, Fatma Sultan Kilic, Kevser Erol, Varol Pabuccuoglu
• Journal: Archiv der Pharmazie (Arch Pharm (Weinheim)) Vol. 340 Issue 12 Pg. 656-60 (Dec 2007) ISSN: 0365-6233 [Print] Germany
• PMID: 18038376 (Publication Type: Journal Article)

Chemical References

• Anticonvulsants
• Phthalimides
• Sulfonamides
• Pentylenetetrazole

Topics

• Animals
• Anticonvulsants (chemical synthesis, chemistry, pharmacology)
• Electroshock
• Magnetic Resonance Spectroscopy
• Male
• Mice
• Pentylenetetrazole
• Phthalimides (chemical synthesis, chemistry, pharmacology)
• Seizures (etiology, prevention & control)
• Structure-Activity Relationship
• Sulfonamides (chemical synthesis, chemistry, pharmacology)