Formation of dihydropyridone- and pyridone-based peptide analogs through aza-annulation of β-enamino ester and amide substrates with α-amido acrylate derivatives

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 1033-1042

  Beholz, Lars G ^a   Benovsky, Petr ^a   Ward, Donald L ^a   Barta, Nancy S ^a   Stille, John R ^a,b  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030987952     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9600520     Document Type: Article

References (73)

1. For reviews on conformationally restricted peptidomimetics, see: (a) Davies, J. S. Amino Acids Pept. 1991, 22, 145.
2. (b) Liskamp, R. M. J. Red. Trav. Chim. Pays-Bas 1994, 113, 1.
3. For a recent review of β-turn topography, see: Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467.
4. (a) Kemp, D. S.; Sun, E. T. Tetrahedron Lett. 1982, 23, 3759.
5. (b) Kemp, D. S.; McNamara, P. Tetrahedron Lett. 1982, 23, 3761.
6. (c) Kemp, D. S.; McNamara, P. E. J. Org. Chem. 1984, 49, 2286.
7. (a) Freidinger, R. M.; Veber, D. F.; Perlow, D. S.; Brooke, J. R.; Saperstein, R. Science 1980, 270, 656.
8. (b) Freidinger, R. M.; Veber, D. F.; Hirschmann, R.; Paege, L. M. Int. J. Pept. Protein Res. 1980, 16, 464.
9. (c) Freidinger, R. M.; Perlow, D. S.; Veber, D. F. J. Org. Chem. 1982, 47, 104.
10. (a) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Snyder, J. P.; Springer, J. P.; Hirshfield, J.; Tristram, E. W.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1986, 29, 251.
11. (b) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1988, 31, 422.
12. Yu, K.-L.; Rajakumar, G.; Srivastava, L. K.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1988, 31, 1430.
13. Zydowsky, T. M.; Dellaria, J. F., Jr.; Nellans, H. N. J. Org. Chem. 1988, 53, 5607.
14. (a) Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647.
15. (b) Sato, K.; Nagai, U. J. Chem. Soc., Perkin Trans. 1 1986, 1231.
16. (c) Nagai, U.; Kato, R.; Sato, K.; Ling, N.; Matsuzaki, T.; Tomotake, Y. In Peptides: Chemistry and Biology, Proceedings of the Tenth American Peptide Symposium; Marshall, G. R., Ed.; Escom: Leiden, 1988; p 129.
17. (d) Nagai, U.; Kato, R. In Peptides: Chemistry, Structure and Biology, Proceedings of the Eleventh American Peptide Symposium; Rivier, J. E., Marshall, G. R., Eds.; Escom: Leiden, 1990; p 653.
18. (e) Bach, A. C., II; Markwalder, J. A.; Ripka, W. C. Int. J. Pept. Protein Res. 1991, 38, 314.
19. (f) Sato, K.; Hotta, M.; Dong, M.-H.; Hu, H.-Y.; Taulene, J. P.; Goodman, M.; Nagai, U.; Ling, N. Int. J. Pept. Protein Res. 1991, 38, 340.
20. (g) Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron 1993, 49, 3577.
21. (a) Moeller, K. D.; Hanau, C. E.; d'Avignon, A. Tetrahedron Lett. 1994, 35, 825.
22. (b) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091.
23. (a) Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861.
24. (b) Dumas, J.-P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1493.
25. (a) Goldman, M. E.; Nunberg, J. H.; O'Brien, J. A.; Quintero, J. C.; Schleif, W. A.; Freund, K. F.; Gaul, S. L.; Saari, W. S.; Wai, J. S.; Huffman, J. M.; Anderson, P. S.; Hupe, D. J.; Emini, E. A.; Stern, A. M. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6863.
26. (b) Saari, W. S.; Hoffman, J. M.; Wai, J. S.; Fisher, T. E.; Rooney, C. S.; Smith, A. M.; Thomas, C. M.; Goldman, M. E.; O'Brien, J. A.; Nunberg, J. H.; Quintero, J. C.; Schleif, W. A.; Emini, E. A.; Stern, A. M.; Anderson, P. S. J. Med. Chem. 1991, 34, 2922.
27. (c) Hoffman, J. M.; Wai, J. S.; Thomas, C. M.; Levin, R. B.; O'Brien, J. A.; Goldman, M. E. J. Med. Chem. 1992, 35, 3784.
28. (d) Houpis, I. N.; Molina, A.; Lynch, J.; Reamer, R. A.; Volante, R. P.; Reider, P. J. J. Org. Chem. 1993, 58, 3176.
29. (d) Damewood, J. R., Jr.; Edwards, P. D.; Feeney, S.; Gomes, B. C.; Steelman, G. B.; Tuthill P. A.; Williams, J. C.; Warner, P.; Woolson, S. A.; Wolanin, D. J.; Veale, C. A. J. Med. Chem. 1994, 37, 3303.
30. (e) Bernstein, P. R.; Andisik, P.; Bradley, P. K.; Bryant, C. B.; Ceccarelli, C.; Damewood, J. R., Jr.; Earley, R.; Edwards, P. D.; Feeney, S.; Gomes, B. C.; Kosmider, B. J.; Steelman, G. B.; Thomas, R. M.; Vacek, E. P.; Veale, C. A.; Williams, J. C.; Wolanin, D. J.; Woolson, S. A. J. Med. Chem. 1994, 37, 3313.
31. (a) Mynderse, J. S.; Samlaska, S. K.; Fukuda, D. S.; Du Bus, R. H.; Baker, P. J. J. Antibiot. 1985, 38, 1003.
32. (b) Hunt, A. H.; Mynderse, J. S.; Samlaska, S. K.; Fukuda, D. S.; Maciak, G. M.; Kirst, H. A.; Occolowitz, J. L.; Swartzendruber, J. K.; Jones, N. D. J. Antibiotics 1988, 41, 771.
33. (c) Fang, F. G.; Danishefsky, S. J. Tetrahedron Lett. 1989, 30, 3621.
34. (d) Wong, P. L.; Moeller, K. D. J. Am. Chem. Soc. 1993, 115, 11434.
35. Paulvannan, K.; Stille, J. R. J. Org. Chem. 1992, 57, 5319.
36. (a) Paulvannan, K.; Schwarz, J. B.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215.
37. (b) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 6673.
38. (c) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613.
39. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669.
40. (e) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575.
41. (a) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 8197.
42. (b) Barta, N. S.; Brode, A.; Stille, J. R. J. Am. Chem. Soc. 1994, 116, 6201.
43. For previous reports of the use of 2-amidoacrylic acid derivatives in aza-annulation, see: (a) Thyagarajan, B. S.; Gopalakrishnan, P. V. Tetrahedron 1964, 20, 1051.
44. (b) Meyer, H.; Bessert, F.; Horstmann, H. Justus Liebigs Ann. Chem. 1978, 1483.
45. (a) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem. Soc., Chem. Commun. 1980, 109.
46. (c) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257.
47. (c) McCabe, R. W.; Young, D. W.; Davies, G. M. J. Chem. Soc., Chem. Commun. 1981, 395.
48. (d) Chiba, T.; Takahashi, T. Chem. Pharm. Bull. 1985, 33, 2731.
49. (e) Chiba, T.; Takahashi, T.; Kaneko, C. Chem. Pharm. Bull. 1985, 33, 4002.
50. (f) Capps, N. K; Davies, G. M.; Loakes, D.; McCabe, R. W.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1991, 3077.
51. (g) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144.
52. (h) Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253.
53. For the importance of β-amino acids, see: (a) Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3.
54. For the importance of β-amino acids, see: (a) Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3.
55. (a) Meyers, A. I.; Nolen, R. L.; Collington, E. W.; Narwid, T. A.; Strickland, R. C. J. Org. Chem. 1973, 38, 1974.
56. (b) Sano, T.; Horiguchi, Y.; Tsuda, Y.; Itatani, Y. Heterocycles 1978, 9, 161.
57. Bonnaud, B.; Bigg, D. C. H. Synthesis 1994, 465.
58. The synthesis of 16b was accomplished through methods described in: Celerier, J. P.; Deloisy-Marchalant, E.; Lhommet, G.; Maitte, P. Org. Synth. 1988, 67, 170.
59. For other applications of 16b and related compounds for azaannulation reactions, see: (a) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1974, 39, 3430. (b) Nagasaka, T.; Inoue, H.; Ichimura, M.; Hamaguchi, F. Synthesis 1982, 848. (c) Nagasaka, T.; Inoue, H.; Hamaguchi, F. Heterocycles 1983, 20, 1099. (d) Brunerie, P.; Célérier, J.-P.; Huché, M.; Lhommet, G. Synthesis 1985, 735. (e) ref 12c. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. (g) Reference 14c. (h) Reference 15a.
60. For other applications of 16b and related compounds for azaannulation reactions, see: (a) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1974, 39, 3430. (b) Nagasaka, T.; Inoue, H.; Ichimura, M.; Hamaguchi, F. Synthesis 1982, 848. (c) Nagasaka, T.; Inoue, H.; Hamaguchi, F. Heterocycles 1983, 20, 1099. (d) Brunerie, P.; Célérier, J.-P.; Huché, M.; Lhommet, G. Synthesis 1985, 735. (e) ref 12c. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. (g) Reference 14c. (h) Reference 15a.
61. For other applications of 16b and related compounds for azaannulation reactions, see: (a) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1974, 39, 3430. (b) Nagasaka, T.; Inoue, H.; Ichimura, M.; Hamaguchi, F. Synthesis 1982, 848. (c) Nagasaka, T.; Inoue, H.; Hamaguchi, F. Heterocycles 1983, 20, 1099. (d) Brunerie, P.; Célérier, J.-P.; Huché, M.; Lhommet, G. Synthesis 1985, 735. (e) ref 12c. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. (g) Reference 14c. (h) Reference 15a.
62. For other applications of 16b and related compounds for azaannulation reactions, see: (a) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1974, 39, 3430. (b) Nagasaka, T.; Inoue, H.; Ichimura, M.; Hamaguchi, F. Synthesis 1982, 848. (c) Nagasaka, T.; Inoue, H.; Hamaguchi, F. Heterocycles 1983, 20, 1099. (d) Brunerie, P.; Célérier, J.-P.; Huché, M.; Lhommet, G. Synthesis 1985, 735. (e) ref 12c. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. (g) Reference 14c. (h) Reference 15a.
63. For other applications of 16b and related compounds for azaannulation reactions, see: (a) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1974, 39, 3430. (b) Nagasaka, T.; Inoue, H.; Ichimura, M.; Hamaguchi, F. Synthesis 1982, 848. (c) Nagasaka, T.; Inoue, H.; Hamaguchi, F. Heterocycles 1983, 20, 1099. (d) Brunerie, P.; Célérier, J.-P.; Huché, M.; Lhommet, G. Synthesis 1985, 735. (e) ref 12c. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. (g) Reference 14c. (h) Reference 15a.
64. For other applications of 16b and related compounds for azaannulation reactions, see: (a) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1974, 39, 3430. (b) Nagasaka, T.; Inoue, H.; Ichimura, M.; Hamaguchi, F. Synthesis 1982, 848. (c) Nagasaka, T.; Inoue, H.; Hamaguchi, F. Heterocycles 1983, 20, 1099. (d) Brunerie, P.; Célérier, J.-P.; Huché, M.; Lhommet, G. Synthesis 1985, 735. (e) ref 12c. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. (g) Reference 14c. (h) Reference 15a.
65. For other applications of 16b and related compounds for azaannulation reactions, see: (a) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1974, 39, 3430. (b) Nagasaka, T.; Inoue, H.; Ichimura, M.; Hamaguchi, F. Synthesis 1982, 848. (c) Nagasaka, T.; Inoue, H.; Hamaguchi, F. Heterocycles 1983, 20, 1099. (d) Brunerie, P.; Célérier, J.-P.; Huché, M.; Lhommet, G. Synthesis 1985, 735. (e) ref 12c. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. (g) Reference 14c. (h) Reference 15a.
66. For other applications of 16b and related compounds for azaannulation reactions, see: (a) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1974, 39, 3430. (b) Nagasaka, T.; Inoue, H.; Ichimura, M.; Hamaguchi, F. Synthesis 1982, 848. (c) Nagasaka, T.; Inoue, H.; Hamaguchi, F. Heterocycles 1983, 20, 1099. (d) Brunerie, P.; Célérier, J.-P.; Huché, M.; Lhommet, G. Synthesis 1985, 735. (e) ref 12c. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. (g) Reference 14c. (h) Reference 15a.
67. Nuclear Overhauser enhancement (NOE) studies on 25 were used to confirm that the stereochemistry of the double bond for the major isomer was E. Irradiation of the vinyl proton resulted in the enhancement of the N-benzyl protons of 3.3% and 1.6%. The relationship of the minor and major isomers, whether isomeric in alkene geometry or cis/trans diasteromers, was not established.
68. 1H NMR. Characteristic peaks of 24c were the following: 2.49 (td, J = 15.9, 3.0 Hz, 1 H), 3.55 (dd, J = 15.9, 6.3 Hz, 1 H), 4.63 (dt, J = 15.1, 6.3 Hz, 1 H).
69. Behringer, H.; Taul, H. Chem. Ber. 1957, 90, 1398.
70. (a) Dobashi, A.; Saito, N.; Motoyama, Y.; Kara, S. J. Am. Chem. Soc. 1986, 108, 307.
71. (b) Jursic, B. S.; Goldberg, S. I. J. Org. Chem. 1992, 57, 7172.
72. Barta, N. S.; Paulvannan, K.; Schwarz, J. B.; Stille, J. R. Synth. Commun. 1994, 24, 853.
73. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.