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0345107319
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note
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1. Dedicated with great admiration and respect to our illustrious chemistry department consultant, Professor Henry Rapoport, Department of Chemistry, University of California at Berkeley, on the occasion of his 80th birthday.
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0013590703
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Boston, MA, August 23-27, Medicinal Chemistry Section, MEDI-073
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2. Portions of this work were presented at the 216th National American Chemical Society Meeting, Boston, MA, August 23-27, 1998; Medicinal Chemistry Section, MEDI-073.
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216th National American Chemical Society Meeting
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3
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77956716245
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Bristol, J. A., Ed.; Academic: San Diego
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3. Recent Reviews: (a) Vacca, J. P. In Ann. Rep. Med. Chem. Bristol, J. A., Ed.; Academic: San Diego, 1998; Vol. 33, 81.
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(c) Ripka, W. C.; Vlasuk G. P. In Ann. Rep. Med. Chem. Bristol, J. A., Ed.; Academic Press: San Diego, 1997; Vol. 32, 71.
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(b) Levy, O. E.; Semple, J. E. ; Lim, M. L.; Reiner, J.; Rote, W. E.; Dempsey, E.; Richard, B. M.; Zhang, E.; Tulinsky, A.; Ripka, W. C.; Nutt, R. F. J. Med. Chem. 1996, 39, 4527.
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(c) Krishnan, R.; Zhang, E.; Hakansson, K.; Arni, R. V.; Tulinsky, A.; Lim-Wilby M. S. L.; Levy, O. E.; Semple, J. E.; Brunck, T. K. Biochemistry 1998, 37, 12094.
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0002369171
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US Patent 5703208, 1997
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(d) Semple, J. E.; Ardecky, R. J.; Nutt, R. F.; Ripka, W. C.; Rowley, D. C.; Lim-Wilby, M. S.; Brunck, T. K. US Patent 5703208, 1997. (Chem. Abstr. 1998, 128: 102391).
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7. Tamura, S. Y.; Goldman, E. G.; Brunck, T. K.; Ripka, W. C.; Semple, J. E. Bioorg. Med. Chem. Lett. 1997, 7, 331.
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8. Tamura, S. Y.; Semple, J. E.; Reiner, J. E.; Goldman, E. A.; Brunck, T. K.; Lim-Wilby, M.; Carpenter, S. H.; Rote, W. E.; Oldschulte, G. L. Richard, B. M.; Nolan, T. G.; Nutt, R. F.; Ripka, W. C. Bioorg. Med. Chem. Lett. 1997, 7, 1543.
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10. For our other recent serine protease inhibitor studies see: (a) Tamura, S. Y.; Shamblin, B. M.; Brunck, T. K.; Ripka, W. C. Bioorg. Med. Chem. Lett. 1997, 7, 1359.
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Ramage, R. Ed.; Mayflower Scientific
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(b) Nutt, R. F.; Semple, J. E.; Levy, O. E.; Nolan, T. G.; Tamura, S. Y.; Ardecky, R. J.; Rowley, D. C.; Lim, M. L.; Ha-Uong, T. Richard, B. M.; Bergum, P. W.; Ripka, W. C. In Peptides 1996. Proc. 24th Eur. Pept. Symp.; Ramage, R. Ed.; Mayflower Scientific, 1997.
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Rowley, D.C.7
Lim, M.L.8
Ha-Uong, T.9
Richard, B.M.10
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Ripka, W.C.12
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0345107312
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US Patent 5658930, 1997
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(c) Tamura, S. Y.; Semple, J. E.; Ripka, W. C.; Ardecky, R. J.; Carpenter S. H.; Ge, Y.; Brunck, T. K.; Nutt, R. F. US Patent 5658930, 1997 (Chem Abstr. 1997, 727: 234607).
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0345107311
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5-mediated intramolecular dehydration using rather vigorous conditions as well as the strong protic acid or base hydrolytic ring-opening reactions under drastic conditions have been described. See (a) Sianesi, E.; Redaelli, R.; Magistretti, M. J.; Massarani, E. J. Med. Chem. 1973, 16, 1122.
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JES acknowledges a reviewer for providing the following precedents of alkoxide-catalyzed ring-opening of saccharin derivatives, see
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(b) Sianesi, E.; Redaelli, R.; Bertani, M.; Da Re, P. Chem. Ber. 1970, 103, 1992. JES acknowledges a reviewer for providing the following precedents of alkoxide-catalyzed ring-opening of saccharin derivatives, see:
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0345538723
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note
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12. All new compounds were characterized by full spectroscopic (NMR, low/high resolution MS) data. Yields refer to spectroscopically and chromatographically homogenous (≥95% by HPLC, TLC) materials.
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0029972959
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13. (a) Tamura, S. Y.; Semple, J. E.; Ardecky, R. J.; Leon, P.; Carpenter, S. H.; Ge, Y.; Shamblin, B. M.; Weinhouse, M. I.; Ripka, W. C.; Nutt, R. F. Tetrahedron Lett. 1996, 37, 4109.
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note
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14. The in vitro enzyme assays were performed according to the protocols described in refs 3 and 4.
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