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Synthesis and Anticonvulsant Evaluation of (R)- and (S)-3-Carbobenzyloxy-amino-1-oxysuccinimides
Corresponding Author(s) : Do-Hun Lee
Asian Journal of Chemistry,
Vol. 25 No. 11 (2013): Vol 25 Issue 11
Abstract
A series of (R)-and (S)-3-carbobenzyloxy-amino-1-oxysuccinimides (5a-d) [(S)-3-carbobenzyloxy-amino-1-benzoyloxysuccinimde, (R)-3-carbobenzyloxy-amino-1-acetyloxysuccinimde, (R)-3-carbobenzyloxy-amino-1,4-nitrobenzoyloxysuccinimde, (R)-3-carbobenzyloxy-amino-1,4-fluorobenzoyloxysuccinimde] were synthesized and investigated their anticonvulsant activities in maximal electric shock seizure test and pentylenetetrazole induced seizure test.
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- (a) J.M. Liebmann and A. Schneider, Ann. Med. Chem., 20, 11 (1985); (b) E.A. Swinyard, Antiepilepic Drug, Ravan Press: New York, edn. 2, p. 5 (1982).
- D. Schmidt, Epilepsia, 25, 244 (1984).
- D. Lindhart and R.J.E.A. Hopperner, Epilepsia, 25, 77 (1984).
- J.A. Vida, In ed.: W.O. Foye, Principle of Medicinal Chemistry, Lea & Febiger: Philadelphia, Ch. 11 (1995).
- (a) H. Kohn, K.N. Sawhney, D. LeGall and J.D. Leader, J. Med. Chem., 34, 2444 (1991); (b) H. Kohn, K.N. Sawhney, D. LeGall and J.D. Cinley, J. Med. Chem., 33, 919 (1990); (c) J.D. Conley and H. Kohn, J. Med. Chem., 30, 567 (1987).
- (a) J. Takahashi, K. Ogui, H. Fujimura, I. Satoda, T. Fukui and Y. Yamamoto, Swiss Patent 393355, Oct. 30 (1965); (b) D.E. Thorne, US Patent. 3657341, April 8 (1972).
- (a) W.J. Brouillette, V.P. Jestkov, M.L. Brown, M.S. Akhatar, T.M. DeLorey and G.B. Brown, J. Med. Chem., 37, 3289 (1994); (b) C.H. Kwon, M.T. Iqbal and J.N.D. Eurpel, J. Med. Chem., 34, 1845 (1991).
- (a) V.A. Farrar, M. Ciechanowicz-Rutkowska, J. Grochowski, P. Serda, G. Filippini, C.N. Hinko, A. El-Assadi, J.A. Moore, I.O. Edafiogho, C.W. Andrew, M. Cory, J.M. Nicholson and K.R. Scott, J. Med. Chem., 36, 3517 (1993); (b) I.O. Edafiogho, K.R. Scitt, J.A. Moore, V.A. Farrar and J.M. Nicholson, J. Med. Chem., 34, 387 (1991); (c) M.R. Borenstein and P.H. Duukas, J. Pharm. Sci., 76, 300 (1987); (d) M.J. Kornet, J. Pharm. Sci., 73, 405 (1984).
- (a) D.T. Witiak, S.K. Seth, E.R. Baizmann, S.L. Weibel and H.H. Wolf, J. Med. Chem., 19, 1419 (1976); (b) H.Y. Aboul-Eneine, C.W. Schauberger, A.R. Hansen and L.J. Fischer, J. Med. Chem., 18, 736 (1975).
- (a) K.E. Andersen, C. Braestrup, F.C. Gronwald, A.S. Jorgensen, E.B. Nielsen, U. Sonnewald, P.O. Sorensen, P.D. Suzdak and L.J.S. Knutsen, J. Med. Chem., 36, 1716 (1993); (b) V. N'Goka, G. Schlewer, J.M. Linget, J.P. Chambon and C.G. Wermuth, J. Med. Chem., 34, 2547 (1991); (c) J.R. Bruke and R.B. Silvermann, J. Am. Chem. Soc., 113, 9329 (1991).
- (a) P.C.K. Pook, D.E. Jane and J.C. Watkins, J. Med. Chem., 37, 4288 (1994); (b) R. Heckendorn, H. Allgeier, J. Baud, W. Grunzenhauser and C. Angst, J. Med. Chem., 36, 3721 (1993).
- For the preparation of compound 4: M. Itoh, Chem. Pharm. Bull., 17, 1679 (1969); For the preparation of compounds 1 and 2: S.R. Sandler and W. Karo, Organic Functional Group Preparation; Academic Press: New York, Vol. 3, p. 253 (1972).
- (a) E.A. Swinyard, J.H. Woodhead, H.S. White and M.R. Franklin, in ed: R. Levy, General Priciples, Experimental Section, Quantification and Evaluation of Anticonvulsants in Antiepileptic Drugs, Ravan Press, New York, edn. 3, p. 88 (1988); (b) R.L. Krall, J.K. Penry, B.G. White, H.J. Kupferberg and C.A. Swinyard, Epilepsia, 19, 409 (1978).
- R.J. Porter, J.J. Cereghino, G.D. Gladding, B.J. Hessie, H.J. Kupferberg, B. Scoville and B.G. White, Cleveland Clin. Q., 51, 283 (1984).
References
(a) J.M. Liebmann and A. Schneider, Ann. Med. Chem., 20, 11 (1985); (b) E.A. Swinyard, Antiepilepic Drug, Ravan Press: New York, edn. 2, p. 5 (1982).
D. Schmidt, Epilepsia, 25, 244 (1984).
D. Lindhart and R.J.E.A. Hopperner, Epilepsia, 25, 77 (1984).
J.A. Vida, In ed.: W.O. Foye, Principle of Medicinal Chemistry, Lea & Febiger: Philadelphia, Ch. 11 (1995).
(a) H. Kohn, K.N. Sawhney, D. LeGall and J.D. Leader, J. Med. Chem., 34, 2444 (1991); (b) H. Kohn, K.N. Sawhney, D. LeGall and J.D. Cinley, J. Med. Chem., 33, 919 (1990); (c) J.D. Conley and H. Kohn, J. Med. Chem., 30, 567 (1987).
(a) J. Takahashi, K. Ogui, H. Fujimura, I. Satoda, T. Fukui and Y. Yamamoto, Swiss Patent 393355, Oct. 30 (1965); (b) D.E. Thorne, US Patent. 3657341, April 8 (1972).
(a) W.J. Brouillette, V.P. Jestkov, M.L. Brown, M.S. Akhatar, T.M. DeLorey and G.B. Brown, J. Med. Chem., 37, 3289 (1994); (b) C.H. Kwon, M.T. Iqbal and J.N.D. Eurpel, J. Med. Chem., 34, 1845 (1991).
(a) V.A. Farrar, M. Ciechanowicz-Rutkowska, J. Grochowski, P. Serda, G. Filippini, C.N. Hinko, A. El-Assadi, J.A. Moore, I.O. Edafiogho, C.W. Andrew, M. Cory, J.M. Nicholson and K.R. Scott, J. Med. Chem., 36, 3517 (1993); (b) I.O. Edafiogho, K.R. Scitt, J.A. Moore, V.A. Farrar and J.M. Nicholson, J. Med. Chem., 34, 387 (1991); (c) M.R. Borenstein and P.H. Duukas, J. Pharm. Sci., 76, 300 (1987); (d) M.J. Kornet, J. Pharm. Sci., 73, 405 (1984).
(a) D.T. Witiak, S.K. Seth, E.R. Baizmann, S.L. Weibel and H.H. Wolf, J. Med. Chem., 19, 1419 (1976); (b) H.Y. Aboul-Eneine, C.W. Schauberger, A.R. Hansen and L.J. Fischer, J. Med. Chem., 18, 736 (1975).
(a) K.E. Andersen, C. Braestrup, F.C. Gronwald, A.S. Jorgensen, E.B. Nielsen, U. Sonnewald, P.O. Sorensen, P.D. Suzdak and L.J.S. Knutsen, J. Med. Chem., 36, 1716 (1993); (b) V. N'Goka, G. Schlewer, J.M. Linget, J.P. Chambon and C.G. Wermuth, J. Med. Chem., 34, 2547 (1991); (c) J.R. Bruke and R.B. Silvermann, J. Am. Chem. Soc., 113, 9329 (1991).
(a) P.C.K. Pook, D.E. Jane and J.C. Watkins, J. Med. Chem., 37, 4288 (1994); (b) R. Heckendorn, H. Allgeier, J. Baud, W. Grunzenhauser and C. Angst, J. Med. Chem., 36, 3721 (1993).
For the preparation of compound 4: M. Itoh, Chem. Pharm. Bull., 17, 1679 (1969); For the preparation of compounds 1 and 2: S.R. Sandler and W. Karo, Organic Functional Group Preparation; Academic Press: New York, Vol. 3, p. 253 (1972).
(a) E.A. Swinyard, J.H. Woodhead, H.S. White and M.R. Franklin, in ed: R. Levy, General Priciples, Experimental Section, Quantification and Evaluation of Anticonvulsants in Antiepileptic Drugs, Ravan Press, New York, edn. 3, p. 88 (1988); (b) R.L. Krall, J.K. Penry, B.G. White, H.J. Kupferberg and C.A. Swinyard, Epilepsia, 19, 409 (1978).
R.J. Porter, J.J. Cereghino, G.D. Gladding, B.J. Hessie, H.J. Kupferberg, B. Scoville and B.G. White, Cleveland Clin. Q., 51, 283 (1984).