Enaminones 11. An examination of some ethyl ester enaminone derivatives as anticonvulsant agents

A modified enaminone model developed from the Unverfeth model to theoretically determine the activity of anticonvulsant enaminone ester analogs. In this paper, we investigated the previously synthesized anticonvulsant enaminone ethyl ester analogs using the computational gaussian 03 programs. The si...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2013-06, Vol.21 (11), p.3272-3279
Main Authors: Alexander, Mariano S., Scott, K.R., Harkless, John, Butcher, Raymond J., Jackson-Ayotunde, Patrice L.
Format: Article
Language:English
Subjects:
Active sites
Aniline Compounds - chemistry
Anticonvulsants - chemistry
Binding Sites
Drug Design
Enaminones
Epilepsy
Esters
Ethanol - analogs & derivatives
Ethanol - chemistry
gaussian programs
Humans
Hydrophobic and Hydrophilic Interactions
Models, Molecular
Molecular modeling
Mulliken charges
Pharmacophore
Static Electricity
Structure-Activity Relationship
Thermodynamics
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Summary:A modified enaminone model developed from the Unverfeth model to theoretically determine the activity of anticonvulsant enaminone ester analogs. In this paper, we investigated the previously synthesized anticonvulsant enaminone ethyl ester analogs using the computational gaussian 03 programs. The significant chemical features of the enaminone compounds that lead to positive anticonvulsant activity were identified. From our analyses, we believe that the neutrality of the phenyl ring may be important for binding in the hydrophobic pocket of the active site and that the binding of the phenyl substituent is the main reason why some analogs are active and others are inactive.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2013.03.036