Design and synthesis of new of 3-(benzo[d]isoxazol-3-yl)-1-substituted pyrrolidine-2, 5-dione derivatives as anticonvulsants

Eur J Med Chem. 2014 Sep 12:84:42-50. doi: 10.1016/j.ejmech.2014.07.016. Epub 2014 Jul 8.

Abstract

A series of 3-(benzo[d]isoxazol-3-yl)-N-substituted pyrrolidine-2, 5-dione (7a-7d, 8a-8d, 9a-9c) have been prepared and evaluated for their anticonvulsant activities. Preliminary anticonvulsant activity was performed using maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) tests after intraperitoneal (ip) injection into mice, which are the most widely employed models for early identification of anticonvulsant candidate. The acute neurological toxicity (NT) was determined applying rotorod test. The quantitative evaluation after oral administration in rats showed that the most active was 3-(benzo[d]isoxazol-3-yl)-1-(4-fluorophenyl) pyrrolidine-2, 5-dione (8a) with ED50 values of 14.90 mg/kg. Similarly the most potent in scPTZ was 3-(benzo[d]isoxazol-3-yl)-1-cyclohexylpyrrolidine-2, 5-dione (7d) with ED50 values of 42.30 mg/kg. These molecules were more potent and less neurotoxic than phenytoin and ethosuximide which were used as reference antiepileptic drugs.

Keywords: Anticonvulsant activity; Benzisoxazole; Pyrrolidine-2, 5-dione; Quantification studies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anticonvulsants / chemical synthesis
  • Anticonvulsants / chemistry
  • Anticonvulsants / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Electroshock
  • Isoxazoles / chemical synthesis
  • Isoxazoles / chemistry
  • Isoxazoles / pharmacology*
  • Mice
  • Molecular Structure
  • Motor Activity / drug effects*
  • Pentylenetetrazole / administration & dosage
  • Rats
  • Rats, Wistar
  • Seizures / drug therapy*
  • Structure-Activity Relationship
  • Succinimides / chemical synthesis
  • Succinimides / chemistry
  • Succinimides / pharmacology*

Substances

  • 3-(benzo(d)isoxazol-3-yl)-1-(4-fluorophenyl)pyrrolidine-2,5-dione
  • 3-(benzo(d)isoxazol-3-yl)-1-cyclohexylpyrrolidine-2,5-dione
  • Anticonvulsants
  • Isoxazoles
  • Succinimides
  • Pentylenetetrazole