Efficient construction of novel quaternary lactam dipeptide surrogates

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6645-6648

  Semple, J Edward ^a  

^a Dendreon   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID; CVS 1578; CVS 1897; DIPEPTIDE; LACTAM DERIVATIVE; PHENYLALANINE; PROLINE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DRUG CONFORMATION; DRUG DESIGN; DRUG SYNTHESIS; ENZYME ACTIVE SITE; STEREOCHEMISTRY;

EID: 0032505201     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0040-4039(98)01431-2     Document Type: Article

References (20)

1. 1. Lactams: (a) Semple, J. E.; Rowley, D. C.; Brunck, T. K.; Ha-Uong, T.; Minami, N. K.; Owens, T. D.; Tamura, S. Y.; Goldman, E. A.; Siev, D. V.; Ardecky, R. J.; Carpenter, S. H.; Ge, Y.; Richard, B. M.; Nolan, T. G.; Hȧkanson, K.; Tulinsky, A.; Nutt, R. F.; Ripka, W. C. J. Med. Chem. 1996, 39, 4531.
2. (b) Semple, J. E.; Ardecky, R. J.; Nutt, R. F.; Ripka, W. C.; Rowley, D. C.; Lim-Wilby, M. S.; Brunck, T. K. US Patent 5,703,208; 1997 (Chem. Abstr. 1998 128, 102391).
3. (c) Tamura, S. Y.; Goldman, E. G.; Brunck, T. K.; Ripka, W. C.; Semple, J. E. Bioorg. Med. Chem. Lett. 1997, 7, 331.
4. 2. Pyridones and related heterocycles: (a) Clive, D. J.; Coltart, D. M. Tetrahedron Lett. 1998, 39, 2519.
5. (b) Tamura, S. Y.; Semple, J. E.; Reiner, J. E.; Goldman, E. A.; Brunck, T. K.; Lim-Wilby, M. S. L.; Carpenter S. H.; Rote, W. E.; Oldschulte, G. L.; Richard, B. M.; Nutt, R. F.; Ripka, W. C. Bioorg. Med. Chem. Lett. 1997, 7, 1543.
6. (c) Sanderson, P. J.; Cutrona, K. J.; Dorsey, B. D.; Dyer, D. L.; McDonough, C. M.; Naylor-Olsen, A. M.; Chen, I. W.; Chen, Z.; Cook, J. J.; Gardell, S. J.; Krueger, J. A.; Lewis, S. D.; Lin, J. H.; Lucas, B. J.; Lyle, E. A.; Lynch, J. J.; Stranieri, M. T.; Vastag, K.; Shafer, J. A.; Vacca, J. P. Bioorg. Med. Chem. Lett. 1998, 8, 817.
7. (d) Dolle, R. E.; Prouty, C. P.; Prasad, C. V. C.; Cook, E.; Saha, A.; Toss, T. M.; Salvino, J. M.; Telaszek, C. T.; Ator, M. A. J. Med. Chem. 1996, 39, 2438.
8. (e) Veale, C. A.; Bernstein, P. R.; Bryant, C.; Ceccarelli, C.; Damewood, Jr., J. R.; Earley, R.; Feeney, S. W.; Gomes, B.; Kosmider, B. J.; Steelman, G. B.; Thomas, R. M.; Vacek, E. P.; Williams, J. C.; Wolanin, D. J.; Woolson, S. J. Med. Chem. 1995, 38, 98.
9. 3. Bicyclic and heterobicyclic lactam manifolds: (a) Review: Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 38, 12789.
10. (b) Shieh, W.-C.; Carlson, J. A.; Zaunius, G. M. J. Org. Chem. 1997, 62, 8271.
11. 4. For syntheses and applications of quaternary lactam systems in other drug candidates see (a) Semple, J. E.; Minami, N. K.; Tamura, S. Y.; Brunck, T. K.; Nutt, R. F.; Ripka, W. C. Bioorg. Med. Chem. Lett. 1997, 7, 2421.
12. (b) Salimbeni, A.; Paleari, F.; Canevotti, R.; Criscuoli, M.; Lippi, A.; Angiolini, M.; Belvisi, L.; Scolastico, C.; Colombo, L. Bioorg. Med. Chem. Lett. 1997, 7, 2205.
13. (c) Colombo, L.; Di Giacomo, M.; Scolastico, C.; Manzoni, L.; Belvisi, L.; Molteni, V. Tetrahedron Lett. 1995, 36, 625.
14. (d) Thaisrivongs, S.; Pals, D. T.; Turner, S. R.; Kroll, L. T. J. Med. Chem. 1988, 31, 1369.
15. (e) Zydowsky, T. M.; Dellaria, J. F.; Nellans, H. N. J. Org. Chem. 1988, 53, 5607.
16. 5. 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.
17. 6. (a) Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
18. (b) Abdel-Magid, A. F.; Harris, B. D.; Maryanoff, C. A. Synlett, 1994, 81.
19. (c) Abdel-Magid, A. F.; Maryanoff, C. A ; Carson, K. G. Tetrahedron Lett. 1990, 37, 5595.
20. 7. Semple, J. E. manuscript in preparation.