Synthesis and pharmacological evaluation of novel 10 -[2- (Difluoromethoxy)benzyl]-20 H,50 H-spiro[8-azabicyclo[3.2.1]- octane-3,40 -imidazolidine]-20 ,50 -diones and their derivatives

Madaiah, M. and Prashanth, M. K. and Revanasiddappa, H. D. and Veeresh, B. (2014) Synthesis and pharmacological evaluation of novel 10 -[2- (Difluoromethoxy)benzyl]-20 H,50 H-spiro[8-azabicyclo[3.2.1]- octane-3,40 -imidazolidine]-20 ,50 -diones and their derivatives. Archiv der Pharmazie, 347 (5). pp. 370-380. ISSN 03656233

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Abstract

A series of novel 1′‐[2‐(difluoromethoxy)benzyl]‐2′H,5′H‐spiro[8‐azabicyclo[3.2.1]octane‐3,4′‐imidazolidine]‐2′,5′‐dione substituted hydantoins (5–32) were synthesized using an appropriate synthetic route and characterized by elemental analysis and spectral data. The novel molecules were screened for anticonvulsant activity in mice by maximal electroshock (MES) and subcutaneous pentylenetetrazol (ScPTZ)‐induced seizure tests. The neurotoxicity was assessed using the rotarod method. Compounds 9, 10, 18, 30, and 31 exhibited anticonvulsant potency against MES seizure and in the ScPTZ model, with lesser neurotoxicity. Some title compounds showed lesser central nervous system depression compared to phenytoin.

Item Type:	Article
Uncontrolled Keywords:	animal experiment, animal model, controlled study, drug synthesis, mouse, nonhuman, unclassified drug, animal, Animals, chemical structure, chemistry, drug screening, drug structure, Molecular Structure, synthesis, male, Male, priority journal, article, 2, Animal, motor activity, Motor Activity, Mice, spectroscopy, drug effects, animal behavior, rotarod test, anticonvulsant activity, neurotoxicity, seizure, Behavior, anticonvulsive agent, spiro compound, Spiro Compounds, ' imdazolidine] 2', 1' 2 (difl uoromethoxy)benzyl 8 (3, 1' 2 (difluoromethoxy)benzyl] 8 (2, 1' 2 (difluoromethoxy)benzyl] 8 (2 cyanobenzene) sulfonyl 2'h, 1' 2 (difluoromethoxy)benzyl 8 (2 fluorophenyl)sulfonyl 2'h, 1' 2 (difluoromethoxy)benzyl 8 (3, 1' 2 (difluoromethoxy)benzyl] 8 (3 chlorophenyl)sulfonyl 2'h, 1' 2 (difluoromethoxy)benzyl 8 (3 fluorophenyl)sulfonyl 2'h, 1' 2 (difluoromethoxy)benzyl 8 (3 methylphenyl) sulfonyl 2'h, 1' 2 (difluoromethoxy)benzyl 8 (4 ethylphenyl)sulfonyl 2'h, 1' 2 (difluoromethoxy)benzyl 8 (4 fluoro 2 methylphenyl)sulfonyl 2 sulfonyl 2'h, 1' 2 (difluoromethoxy)benzyl 8 (4 methoxyphenyl)sulfonyl 2'h, 1' 2 (difluoromethoxy)benzyl 8 (4 methylbenzyl)sulfonyl 2'h, 1' 2 (difluoromethoxy)benzyl 8 (4-methylphenyl)sulfonyl-2'h, 1' 2 (difluoromethoxy)benzyl n (2 chloro 4, 1' 2 (difluoromethoxy)benzyl n (2 chlorophenyl) 2', 1' 2 (difluoromethoxy)benzyl n (3, 1' 2 (difluoromethoxy)benzyl n (3 chlorophenyl) 2', 1' 2 (difluoromethoxy)benzyl n (3 cyanobenzene) 2', 1' 2 (difluoromethoxy)benzyl n (3 ethylphenyl) 2', 1' 2 (difluoromethoxy)benzyl n (3 fluorophenyl) 2', 1' 2 (difluoromethoxy)benzyl n (3 methylphenyl) 2', 1' 2 (difluoromethoxy)benzyl n (4 fluorophenyl) 2', 1' 2 (difluoromethoxy)benzyl n 2 (propan 2 yl)phenyl 2', 1' 2 (difluoromethoxy)benzyl n 4 (methylsulfanyl) phenyl 2', 1' 2 (difluoromethoxy)benzyl n 4 (propan 2 yl)phenyl 2', 1' 2 (difluoromethoxy)benzyl n phenyl 2', 1'2 (difluoromethoxy)benzyl 8 (2 methylphenyl)sulfonyl 2'h, 1'2 (difluoromethoxy)benzyl 8 (3 bromophenyl)sulfonyl 2'h, 1octane 3, 1octane3, 4 dimethylphenyl)sulfonyl 2'h, 4 imidazolidine 2', 4 imidazolidine 8 carboxamide, 4 imidazolidine 8 carnoxamide, 4' imdazolidine 8 carboxamide, 4' imidazolidine, 4' imidazolidine 2', 4' imidazolidine 2', 4' imidazolidine 8 carboxamide, 5 dimethylphenyl) 2', 5 dimethylphenyl)sulfonyl 2'h, 5 dione, 5' dione, 5' dioxospiro8 azabicyclo3, 5' dioxospiro8 azabicylco3, 5' dixospiro8 azabicyclo3, 5'h spiro8 azabicyclo3, 5'h spiroazabicyclo3, 6 dimethylphenyl) 2', Anticonvulsants, Azabicyclo Compounds, azabicyclo derivative, central nervous system depression, electric shock, hydantoin derivative, imidazolidine derivative, Imidazolidines, Rotarod Performance Test, Seizures
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Arshiya Kousar Library Assistant
Date Deposited:	29 Jun 2019 09:29
Last Modified:	29 Jun 2019 09:29
URI:	http://eprints.uni-mysore.ac.in/id/eprint/3979

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