title: Novel limonene and citral based 2,5-disubstituted-1,3,4-oxadiazoles: a natural product coupled approach to semicarbazones for antiepileptic activity.
abstract: Two novel series of N(4)-(5-(2/3/4-substituted-phenyl)-1,3,4-oxadiazol-2-yl)-N(1)-(2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene)semicarbazide and N(4)-(5-(2/3/4-substituted-phenyl)-1,3,4-oxadiazol-2-yl)-N(1)-(3,7-dimethylocta-3,6-dienylidene)-semicarbazide were synthesized to meet structural prerequisite indispensable for anticonvulsant activity. The anticonvulsant activities of the compounds were investigated using maximal electroshock seizure (MES), subcutaneous pentylenetrtrazole (scPTZ) and subcutaneous strychnine (scSTY) models. The rotorod test was conducted to evaluate neurotoxicity. Some of the selected active compounds were subjected to GABA assay to confirm their mode of action. The outcome of the present investigations proved that the four binding sites pharmacophore model is vital for anticonvulsant activity. The efforts were also made to establish structure-activity relationships among test compounds.
authors.affiliation: Medicinal Chemistry Research Laboratory, SLT Institute of Pharmaceutical Sciences, Guru Ghasidas University, Bilaspur 495 009, CG, India. harishdops@yahoo.co.in
authors.forename: Harish
authors.initials: H
authors.lastname: Rajak
authors.forename: Bhupendra
authors.initials: B
authors.lastname: Singh Thakur
authors.forename: Avineesh
authors.initials: A
authors.lastname: Singh
authors.forename: Kamlesh
authors.initials: K
authors.lastname: Raghuvanshi
authors.forename: Anil Kumar
authors.initials: AK
authors.lastname: Sah
authors.forename: Ravichandran
authors.initials: R
authors.lastname: Veerasamy
authors.forename: Prabodh Chander
authors.initials: PC
authors.lastname: Sharma
authors.forename: Rajesh
authors.initials: R
authors.lastname: Singh Pawar
authors.forename: Murli Dhar
authors.initials: MD
authors.lastname: Kharya
mesh_terms: D000080462:Acyclic Monoterpenes; D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001665:Binding Sites; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D004195:Disease Models, Animal; D000077222:Limonene; D039821:Monoterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011485:Protein Binding / Q000187:drug effects; D051381:Rats; D012640:Seizures / Q000188:drug therapy; D012664:Semicarbazones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005680:gamma-Aminobutyric Acid / Q000378:metabolism
chemical_list: D000080462:Acyclic Monoterpenes; D000927:Anticonvulsants; D053138:Cyclohexenes; D039821:Monoterpenes; D010069:Oxadiazoles; D012664:Semicarbazones; D013729:Terpenes; D005680:gamma-Aminobutyric Acid; D000077222:Limonene; C007076:citral