A crystal-state,solution and theoretical study of the preferred conformation of linear Cα,α-diphenylglycine derivatives and dipeptides with potential anticonvulsant activity |
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Authors: | CLAUDIO TONIOLO MARCO CRISMA NICOLETTA FABIANO PIETRO MELCHIORRI LUCIA NEGRI JEANETTE A KRAUSE DRAKE S EGGLESTON |
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Abstract: | Several linear molecules containing the Cα,α-diphenylglycine residue were prepared as potential anticonvulsants. The conformational preferences of the Cα,α-diphenylglycine residue were assessed in these synthetic derivatives and dipeptides by X-ray diffraction, FTIR absorption and 1H NMR techniques, and by conformational energy computations. Five (out of six) derivatives adopt the fully extended C5 conformation in the crystal state. This intramolecularly H-bonded form is largely populated in chloroform solution in all the derivatives investigated. Conformational energy computations in vacuo support the view that the intramolecularly H-bonded C7-ring form is the most stable structure for these compounds. Only one linear derivative exhibits a (modest) anticonvulsant activity. |
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Keywords: | Cα α -diphenylglycine dipeptides crystal structure C5 conformation energy computations C7-ring conformation anticonvulsants |
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