Ethylphenacemide and phenacemide: conformational similarities to diphenylhydantoin and stereochemical basis of anticonvulsant activity.
The three-dimensional molecular structures of the potent anticonvulsant agents phenacemide and ethylphenacemide have been determined by single-crystal x-ray diffraction. Although these compounds possess straight-chain acetylurea groupings, in the crystalline state both molecules adopt a pseudocyclic conformation of the acetylurea chain through amide...carbonyl oxygen intramolecular hydrogen bonding. This results in spatial positioning and relative orientation of two electron-donating functional groups in these molecules similar to those of comparable atoms in diphenylhydantoin and other heterocycle-containing anticonvulsants.
D000927:Anticonvulsants; D044482:Benzeneacetamides; D008958:Models, Molecular; D008968:Molecular Conformation; D010648:Phenylacetates; D010672:Phenytoin; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014508:Urea / Q000031:analogs & derivatives*; D014961:X-Ray Diffraction
D000927:Anticonvulsants; D044482:Benzeneacetamides; D010648:Phenylacetates; D010672:Phenytoin; C005825:pheneturide; D014508:Urea; C005396:phenacemide
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