Synthesis and Pharmacological Evaluation of New 2-Substituted-5-{2-[(2-halobenzyl)thio)phenyl}-1,3,4-oxadiazoles as Anticonvulsant Agents

Abstract

A new series of 2-substituted-5-{2-[(2-halobenzyl)thio)phenyl}-1,3,4oxadiazoles was designed, synthesized and investigated for anticonvulsant activities. The designed compounds contain the main essential pharmacophore for binding to the benzodiazepine receptors. Conformational analysis and superimposition of energy minima conformers of designed molecules on estazolam, a known benzodiazepine receptor agonist, revealed that the main characteristics of the proposed benzodiazepine pharmacophore were well matched. Electroshock and pentylenetetrazole-induced lethal convulsion tests showed that some of the synthesized compounds had significant anticonvulsant activity. The structureactivity relationship study of these compounds indicated that the introduction of an amino group at position 2 of 1,3,4-oxadiazole ring and a fluoro substituent at the ortho position of the benzylthio moiety had the best anticonvulsant activity.

1H and 13C NMR characterization of 1,3,4‐oxadiazole derivatives

“…The reaction mixture was stirred at room temperature for 18 hr and was poured into water (30 ml). After extraction with methylene chloride (20 mL × 2), the combined organic layers were dried over MgSO 4 . Filtration and evaporation of the organic solvent gave a crude solid, which was purified with methanol to yield 9 (yield: 35%, m.p: 180-182°C).…”

“…[1] Among these, the 1,3,4-oxadiazole skeleton has garnered considerable interest owing to its diverse biological properties including anti-inflammatory, antimicrobial, anticonvulsant, antitubercular, antiviral, and anticancer activities. [2][3][4][5][6][7] 1,3,4-Oxadiazole is called oxybiazole. [8] 4H-chromen-4-one makes up flavone, which is a plantderived secondary metabolite.…”

Novel 4-thiazolidinone derivatives as agonists of benzodiazepine receptors: design, synthesis and pharmacological evaluation

“…Furthermore, the previously reported article revealed that thiazolidinone derivatives exhibit anticonvulsant activity (Tripathi et al, 2014[21]). Based on these evidences and our earlier published papers on flexible novel heterocyclic compounds (Akbarzadeh et al, 2003[1]; Almasirad et al, 2004[4]; Zarghi et al, 2005[24]; Almasirad et al, 2007[5]; Zarghi et al, 2008[22]; Mahdavi et al, 2010[13]; Faizi et al, 2012[7]; Tabatabai et al, 2013[20]; Zarghi et al, 2008[22][23]; Faizi, et al, 2015[6]) , some new thiazolidinone derivatives that have the essential pharmacophore groups for binding to the BZD's receptors were developed (Figure 1(Fig. 1)).…”

Synthesis and Characterization of 1,3,4-Oxadiazoles Derivatives from 1,2,3,4-Tetrahydroisoquinoline and their Bioevalution (Antibacterial & Antifungal)

“…1,3,4-Oxadiazole was found to possess a wide spectrum of pharmacological activity such as antibacterial [3][4] , anti fungal [5][6] , anthelminitic 7 , anti tubercular 8 , anti-infective 9 , anti cancer 10 , anti-HIV 11 , anti oxidant 12 , analgesic [13][14] , anti histanamic 15 , insectivdal 16 , anti-inflammatory 17 , and anti convulsant [18][19] .…”