PMID: 11311072Apr 20, 2001Paper

Synthesis and structural studies of aza analogues of functionalized amino acids: new anticonvulsant agents

Journal of Medicinal Chemistry
S V AndurkarH Kohn

Abstract

We have reported that functionalized amino acids 1 display potent anticonvulsant activities in mice and rats, and that the activity resides primarily in the D-isomer. In this study we investigated whether selectively replacing the C(2) tetrahedral atom with a trivalent nitrogen provides compounds with comparable activity. Six functionalized N(2)-substituted semicarbazides (3) were prepared. X-ray crystallographic analysis of 1-acetyl-4-benzyl-2-(thiazol-2-yl)semicarbazide (13) showed that it lost asymmetry and adopted a configuration midway between the corresponding D- and L-amino acid derivatives. Evaluation of 3 in both mice (ip) and rats (po) showed that the compounds exhibited significant anticonvulsant activities but in most cases at levels lower than their amino acid counterparts. One of the semicarbazides, 13, displayed excellent activity in mice and rats that compared favorably to that of phenytoin.

References

Jul 31, 1984·Biochemical and Biophysical Research Communications·W J GreenleeT C Vassil
Jan 1, 1984·Cleveland Clinic Quarterly·R J PorterB G White

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Citations

Nov 1, 2003·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·P YogeeswariJ P Stables
Sep 3, 2003·Bioorganic & Medicinal Chemistry·Cécile BéguinHarold Kohn
Aug 3, 2011·Future Medicinal Chemistry·Caroline ProulxWilliam D Lubell
Apr 20, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Monika WujecPiotr Paneth
Jul 28, 2004·European Journal of Medicinal Chemistry·Perumal YogeeswariDharmarajan Sriram
Dec 30, 2014·European Journal of Medicinal Chemistry·Chandra Bhushan MishraManisha Tiwari
Oct 8, 2019·Chemical Science·Alexander J KasznelDavid M Chenoweth
Feb 21, 2021·Journal of Inorganic Biochemistry·Joanna WątłyMagdalena Rowińska-Żyrek

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