Synthesis and anticonvulsant properties of 2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-ones

Abstract

A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-ones were synthesized and evaluated for anticonvulsant activity in DBA/2 mice against sound-induced seizures and in rats against maximal electroshock-induced seizures. Most of the derivatives showed an anticonvulsant effect better than that of valproate, a commonly used anticonvulsant drug. Compound 3 possessed an anticonvulsant activity comparable to that of diphenylhydantoin in both tests and was selected for further studies. Structure-activity relationships are discussed.

Synthesis and Structural Features of New Cyclofunctionalized Benzimidazoles

“…MS spectra show correct molecular ion and fragmentations that are in agreement with the proposed structures. 13 C-NMR spectra give conclusive evidence for the structural assignment of the synthesized compounds.…”

“…This effort has resulted in the preparation of several 1H,3Hthiazolo [3,4-a]benzimidazoles (TBZs), some of which were found to be potent inhibitors of HIV-1 induced cytopathicity and virus replication. [4][5][6][7][8][9][10][11][12] Moreover, in our previous papers, [13][14][15] the introduction of a pyrrole nucleus on benzimidazole system resulted in generally active compounds endowed with anticonvulsant properties better than that of valproate and comparable to that of phenytoin.…”

Anticonvulsant Potency of 10 Various P-Isopropoxyphenylsuccinimide Derivatives in the Maximal Electroshock-Induced Seizure Threshold Model in Mice

“…Such constituents are the nitrogenous heteroatomic system, at least one phenyl ring, and either additional phenyl nucleus or an alkyl substituent attached to the heterocycle [2,3]. These attributes are, partially or fully, characteristic for a well-established antiepileptic drug -ethosuximide (3-ethyl-3-methyl-pyrrolidine-2,5-dione), which belongs to the succinimide class.…”

Synthesis and Anticonvulsant Properties of Some N-Aryl and N-Arylaminomethyl Derivatives of 3-P-Isopropoxyphenylpyrrolidine-2,5-Dione

“…In spite of the structural diversity of the antiepileptic drugs, some common chemical structures responsible for their therapeutic anticonvulsant action have been denoted. Such chemical elements consist of a nitrogenous heteroatomic system, one phenyl ring, and either additional phenyl nucleus or an alkyl substituent attached to the heterocycle (3,4). Of note, these elements comprise the well-established antiepileptic drug ñ ethosuximide (3-ethyl-3methyl-pyrrolidine-2,5-dione) that belongs to the succinimide class.…”