• YAKHAK HOEJI
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• v.45 no.1
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• pp.7-15
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• 2001

For the purpose of defining the effects of N-acyl groups on the anticonvulsant activities of N-acyl-$\alpha$-amino-glutarimides, various (R)- and (S)-N-acyl-$\alpha$-aminoglutarimide were prepared from the corresponding N-Cbz-glutamic acid and were evaluated their anticonvulsant activities in the MES and PTZ test, including their neurotoxicities. Among the tested compounds, only (R) N-cinnamoyl-$\alpha$-amino-N-methylglutarimide showed anticonvulsant activity in the MES and PTZ test. And the other tested compounds was active in the only PTZ test. The order of anticonvulsant activities in the PTZ test was as followes; for the (R) series, N-4-methoxycinnamoyl = cinnamoyl > N-4-nitrobenzoyl > N-benzoyl > N-phenylacetyl; for the (S) series, N-4-methoxycinnamoyl = N-3-nitrobenzoyl > N-4-nitrobenzoyl = N-cinnamoyl = N-phenylacetyl. From the above results, it was conceivable that the substituted N-acyl group had important effects on the anticonvulsant activities of these compounds. However stereoisomeric deferences in the anticonvulsant activities were not exhibited clearly.

• Journal of Life Science
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• v.14 no.1
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• pp.91-97
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• 2004

As a part of our study on the improvement of anticonvulsant, here we report the synthesis of N-acyl-$\alpha$-aminosuc-cinimides 1 and N-acyl-$\alpha$-aminoglutarimides 2. (R)-Benzoic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-ylester 6a, (R)-4-nifro-benzoic acid 4-benzyloxycarbonylamino-2- oxo-pyrrolidin-1-yl ester 6b, (R) -4-nitro-benzoic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl ester 6c, and (R)-propionic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl ester 6d were synthesized from (R)-2-benzyloxy carbonylamino-succinic acid 3 as a starting meterial. (R)-(3- Benzyloxycarbonylamino-2,6-dioxo-piperidin-1-yloxy)-acetic acid methyl ester 10a, (R)-(3-benzyloxycarbonylamino-2,6-dioxo-piperidin-1-yloxy)-acetic acid ethy1 ester 10b, an d (R)-2-(3-benzyloxycarbonylamino-2,6- diox o-piperidin-1-yl oxy)-propionic acid methyl ester l0c were synthesized from (R)- 3-carbobenzyloxy-amino-glutarmic acid 7 as a starting meterial. The yield, mp, IR, $^1H-NMR,\; and^{13}C$- NMR spectra of the products 6a, 6b, 6c, 6d, 10a, l0b, l0c are summarized in footnote. The biological studies of these compounds are in progress and will be reported in future.