Synthesis of Conformationally-Constrained Glutamate Analogues of the Antitumor Agents DDATHF, LY254155, and LY231514

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5392-5403

  Taylor, Edward C ^a   Jennings, Lee D ^a   Mao, Zhenmin ^a   Hu, Baihua ^a   Jun, Jong Gab ^a   Zhou, Ping ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001324318     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9703459     Document Type: Article

References (42)

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2. For leading references to the use of conformationally-constrained α-amino acids as bioactive agents and for conformational probes of active sites, see: (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (b) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 1, 113. (c) Gainnis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (d) Mendel, D.; Ellman, J.; Schultz, P. G. J. Am. Chem. Soc. 1993, 115, 4359. (e) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett 1944, 575. (f) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
3. For leading references to the use of conformationally-constrained α-amino acids as bioactive agents and for conformational probes of active sites, see: (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (b) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 1, 113. (c) Gainnis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (d) Mendel, D.; Ellman, J.; Schultz, P. G. J. Am. Chem. Soc. 1993, 115, 4359. (e) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett 1944, 575. (f) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
4. For leading references to the use of conformationally-constrained α-amino acids as bioactive agents and for conformational probes of active sites, see: (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (b) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 1, 113. (c) Gainnis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (d) Mendel, D.; Ellman, J.; Schultz, P. G. J. Am. Chem. Soc. 1993, 115, 4359. (e) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett 1944, 575. (f) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
5. For leading references to the use of conformationally-constrained α-amino acids as bioactive agents and for conformational probes of active sites, see: (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (b) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 1, 113. (c) Gainnis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (d) Mendel, D.; Ellman, J.; Schultz, P. G. J. Am. Chem. Soc. 1993, 115, 4359. (e) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett 1944, 575. (f) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
6. For leading references to the use of conformationally-constrained α-amino acids as bioactive agents and for conformational probes of active sites, see: (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (b) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 1, 113. (c) Gainnis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (d) Mendel, D.; Ellman, J.; Schultz, P. G. J. Am. Chem. Soc. 1993, 115, 4359. (e) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett 1944, 575. (f) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
7. Duch, D. S.; Banks, S.; Dev, I. K.; Dickerson, S. H.; Ferone, R.; Heath, L. S.; Humphreys, J.; Knick, V.; Pendergast, W.; Singer, S.; Smith, G. K.; Waters, K.; Wilson, H. R. Cancer Res. 1993, 53, 810.
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16. (a) Shih, C.; Taylor, E. C. US Patent 4,882,334.
17. (b) Habeck, L. L.; Leitner, T. A.; Shackelford, K. A.; Gossett, L. S.; Schultz, R. M.; Andis, S. L.; Shih, C.; Grindey, G. B.; Mendelsohn, L. G. Cancer Res. 1994, 54, 1021.
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19. (b) Taylor, E. C.; Kuhnt, D.; Shih, C.; Rinzel, S. M.; Grindey, G. B.; Barredo, J.; Jannatipour, M.; Moran, R. G. J. Med. Chem. 1992, 35, 4450.
20. For recent work characterizing 14 as a multitargeted antifolate (MTA), see: (a) Shih, C.; Gossett, L. S.; Gates, S. B.; MacKellar, W. C.; Mendelsohn, L. G.; Soose, D. J.; Patel, V. F.; Kohler, W.; Ratnam, M. Proc. NCI-EORTC Symp. New Drugs in Cancer Ther., 9th 1996, 289, 85. (b) Schultz, R. M.; Andis, S. L.; Chen, V. J.; Mendelsohn, L. G.; Patel, V. F.; Shih, C.; Houghton, J. Ibid. 1996, 290, 85. (c) Schultz, R. M.; Andis, S. L.; Bewley, J. R.; Chen, V. J.; Habeck, L. L.; Mendelsohn, L. G.; Patel, V. F.; Rutherford, P. G.; Self, T. D.; Shih, C.; Theobald, K. S.; Worzalla, J. F.; Houghton, J. Proc. Am. Assoc. Cancer Res. 1996, 37, 380. (d) Chen, V. J.; Bewley, J. R.; Gossett, L. S.; Shih, C.; Soose, D. J.; Patel, V. F.; Gates, S. B.; MacKellar, W. C.; Habeck, L. L.; Shackelford, K. A.; Mendelsohn, L. G.; Kohler, W.; Ratnam, M. Ibid. 1966, 37, 381.
21. For recent work characterizing 14 as a multitargeted antifolate (MTA), see: (a) Shih, C.; Gossett, L. S.; Gates, S. B.; MacKellar, W. C.; Mendelsohn, L. G.; Soose, D. J.; Patel, V. F.; Kohler, W.; Ratnam, M. Proc. NCI-EORTC Symp. New Drugs in Cancer Ther., 9th 1996, 289, 85. (b) Schultz, R. M.; Andis, S. L.; Chen, V. J.; Mendelsohn, L. G.; Patel, V. F.; Shih, C.; Houghton, J. Ibid. 1996, 290, 85. (c) Schultz, R. M.; Andis, S. L.; Bewley, J. R.; Chen, V. J.; Habeck, L. L.; Mendelsohn, L. G.; Patel, V. F.; Rutherford, P. G.; Self, T. D.; Shih, C.; Theobald, K. S.; Worzalla, J. F.; Houghton, J. Proc. Am. Assoc. Cancer Res. 1996, 37, 380. (d) Chen, V. J.; Bewley, J. R.; Gossett, L. S.; Shih, C.; Soose, D. J.; Patel, V. F.; Gates, S. B.; MacKellar, W. C.; Habeck, L. L.; Shackelford, K. A.; Mendelsohn, L. G.; Kohler, W.; Ratnam, M. Ibid. 1966, 37, 381.
22. For recent work characterizing 14 as a multitargeted antifolate (MTA), see: (a) Shih, C.; Gossett, L. S.; Gates, S. B.; MacKellar, W. C.; Mendelsohn, L. G.; Soose, D. J.; Patel, V. F.; Kohler, W.; Ratnam, M. Proc. NCI-EORTC Symp. New Drugs in Cancer Ther., 9th 1996, 289, 85. (b) Schultz, R. M.; Andis, S. L.; Chen, V. J.; Mendelsohn, L. G.; Patel, V. F.; Shih, C.; Houghton, J. Ibid. 1996, 290, 85. (c) Schultz, R. M.; Andis, S. L.; Bewley, J. R.; Chen, V. J.; Habeck, L. L.; Mendelsohn, L. G.; Patel, V. F.; Rutherford, P. G.; Self, T. D.; Shih, C.; Theobald, K. S.; Worzalla, J. F.; Houghton, J. Proc. Am. Assoc. Cancer Res. 1996, 37, 380. (d) Chen, V. J.; Bewley, J. R.; Gossett, L. S.; Shih, C.; Soose, D. J.; Patel, V. F.; Gates, S. B.; MacKellar, W. C.; Habeck, L. L.; Shackelford, K. A.; Mendelsohn, L. G.; Kohler, W.; Ratnam, M. Ibid. 1966, 37, 381.
23. For recent work characterizing 14 as a multitargeted antifolate (MTA), see: (a) Shih, C.; Gossett, L. S.; Gates, S. B.; MacKellar, W. C.; Mendelsohn, L. G.; Soose, D. J.; Patel, V. F.; Kohler, W.; Ratnam, M. Proc. NCI-EORTC Symp. New Drugs in Cancer Ther., 9th 1996, 289, 85. (b) Schultz, R. M.; Andis, S. L.; Chen, V. J.; Mendelsohn, L. G.; Patel, V. F.; Shih, C.; Houghton, J. Ibid. 1996, 290, 85. (c) Schultz, R. M.; Andis, S. L.; Bewley, J. R.; Chen, V. J.; Habeck, L. L.; Mendelsohn, L. G.; Patel, V. F.; Rutherford, P. G.; Self, T. D.; Shih, C.; Theobald, K. S.; Worzalla, J. F.; Houghton, J. Proc. Am. Assoc. Cancer Res. 1996, 37, 380. (d) Chen, V. J.; Bewley, J. R.; Gossett, L. S.; Shih, C.; Soose, D. J.; Patel, V. F.; Gates, S. B.; MacKellar, W. C.; Habeck, L. L.; Shackelford, K. A.; Mendelsohn, L. G.; Kohler, W.; Ratnam, M. Ibid. 1966, 37, 381.
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