A versatile synthesis of a β-turn peptidomimetic scaffold: An approach towards a designed model antagonist of the tachykinin NK-2 receptor

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 13, 1996, Pages 1567-1572

  Hanessian, Stephen ^a   McNaughton Smith, Grant ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NEUROKININ A; NEUROKININ B; SUBSTANCE P; TACHYKININ; TACHYKININ RECEPTOR;

AMINO ACID SUBSTITUTION; ARTICLE; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030576293     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00275-2     Document Type: Article

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24. 9. For recent reviews on peptidomimetics see, Peptide Secondary Structure Mimetics. Tetrahedron Symposia-inprint no. 50, Kahn, M., Ed., 1993, 49, 3433-3689; Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Kahn, M. Synlett 1993, 821; see also Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G.R. J. Org. Chem. 1996, 61, 1198; Mueller, R.; Revesz. L. Tetrahedron Lett. 1994, 35, 4091; Robl, J. Tetrahedron Lett. 1994, 35, 393; Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Comm. 1993, 935; Liskamp, R. M. J. Rec. Rev. 1994, 113, 1; Nagai, U.; Sato. K. Tetrahedron Lett. 1985, 26, 647.
25. 9. For recent reviews on peptidomimetics see, Peptide Secondary Structure Mimetics. Tetrahedron Symposia-inprint no. 50, Kahn, M., Ed., 1993, 49, 3433-3689; Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Kahn, M. Synlett 1993, 821; see also Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G.R. J. Org. Chem. 1996, 61, 1198; Mueller, R.; Revesz. L. Tetrahedron Lett. 1994, 35, 4091; Robl, J. Tetrahedron Lett. 1994, 35, 393; Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Comm. 1993, 935; Liskamp, R. M. J. Rec. Rev. 1994, 113, 1; Nagai, U.; Sato. K. Tetrahedron Lett. 1985, 26, 647.
26. 9. For recent reviews on peptidomimetics see, Peptide Secondary Structure Mimetics. Tetrahedron Symposia-inprint no. 50, Kahn, M., Ed., 1993, 49, 3433-3689; Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Kahn, M. Synlett 1993, 821; see also Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G.R. J. Org. Chem. 1996, 61, 1198; Mueller, R.; Revesz. L. Tetrahedron Lett. 1994, 35, 4091; Robl, J. Tetrahedron Lett. 1994, 35, 393; Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Comm. 1993, 935; Liskamp, R. M. J. Rec. Rev. 1994, 113, 1; Nagai, U.; Sato. K. Tetrahedron Lett. 1985, 26, 647.
27. 9. For recent reviews on peptidomimetics see, Peptide Secondary Structure Mimetics. Tetrahedron Symposia-inprint no. 50, Kahn, M., Ed., 1993, 49, 3433-3689; Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Kahn, M. Synlett 1993, 821; see also Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G.R. J. Org. Chem. 1996, 61, 1198; Mueller, R.; Revesz. L. Tetrahedron Lett. 1994, 35, 4091; Robl, J. Tetrahedron Lett. 1994, 35, 393; Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Comm. 1993, 935; Liskamp, R. M. J. Rec. Rev. 1994, 113, 1; Nagai, U.; Sato. K. Tetrahedron Lett. 1985, 26, 647.
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32. 12. For recent reviews, see, Casiraghi, G.; Zanandi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677; Casiraghi, G.; Spanu, P. Synthesis, 1995, 607; see also Martin, S.F.; Barr, K.J. J. Am. Chem. Soc., 1996, 118, 3299; Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011; Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773; Martin, S. F; Corbett, J. W. Synthesis 1992, 55; Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G. Tetrahedron 1992, 48, 727; Harding, K. E; Coleman, M. T; Liu, L.T. Tetrahedron Lett. 1991, 32, 3795; Thaning, M.; Wistrand, L-G. J. Org. Chem. 1990, 55, 1406; Speckamp, W. M.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
33. 12. For recent reviews, see, Casiraghi, G.; Zanandi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677; Casiraghi, G.; Spanu, P. Synthesis, 1995, 607; see also Martin, S.F.; Barr, K.J. J. Am. Chem. Soc., 1996, 118, 3299; Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011; Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773; Martin, S. F; Corbett, J. W. Synthesis 1992, 55; Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G. Tetrahedron 1992, 48, 727; Harding, K. E; Coleman, M. T; Liu, L.T. Tetrahedron Lett. 1991, 32, 3795; Thaning, M.; Wistrand, L-G. J. Org. Chem. 1990, 55, 1406; Speckamp, W. M.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
34. 12. For recent reviews, see, Casiraghi, G.; Zanandi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677; Casiraghi, G.; Spanu, P. Synthesis, 1995, 607; see also Martin, S.F.; Barr, K.J. J. Am. Chem. Soc., 1996, 118, 3299; Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011; Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773; Martin, S. F; Corbett, J. W. Synthesis 1992, 55; Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G. Tetrahedron 1992, 48, 727; Harding, K. E; Coleman, M. T; Liu, L.T. Tetrahedron Lett. 1991, 32, 3795; Thaning, M.; Wistrand, L-G. J. Org. Chem. 1990, 55, 1406; Speckamp, W. M.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
35. 12. For recent reviews, see, Casiraghi, G.; Zanandi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677; Casiraghi, G.; Spanu, P. Synthesis, 1995, 607; see also Martin, S.F.; Barr, K.J. J. Am. Chem. Soc., 1996, 118, 3299; Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011; Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773; Martin, S. F; Corbett, J. W. Synthesis 1992, 55; Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G. Tetrahedron 1992, 48, 727; Harding, K. E; Coleman, M. T; Liu, L.T. Tetrahedron Lett. 1991, 32, 3795; Thaning, M.; Wistrand, L-G. J. Org. Chem. 1990, 55, 1406; Speckamp, W. M.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
36. 12. For recent reviews, see, Casiraghi, G.; Zanandi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677; Casiraghi, G.; Spanu, P. Synthesis, 1995, 607; see also Martin, S.F.; Barr, K.J. J. Am. Chem. Soc., 1996, 118, 3299; Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011; Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773; Martin, S. F; Corbett, J. W. Synthesis 1992, 55; Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G. Tetrahedron 1992, 48, 727; Harding, K. E; Coleman, M. T; Liu, L.T. Tetrahedron Lett. 1991, 32, 3795; Thaning, M.; Wistrand, L-G. J. Org. Chem. 1990, 55, 1406; Speckamp, W. M.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
37. 12. For recent reviews, see, Casiraghi, G.; Zanandi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677; Casiraghi, G.; Spanu, P. Synthesis, 1995, 607; see also Martin, S.F.; Barr, K.J. J. Am. Chem. Soc., 1996, 118, 3299; Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011; Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773; Martin, S. F; Corbett, J. W. Synthesis 1992, 55; Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G. Tetrahedron 1992, 48, 727; Harding, K. E; Coleman, M. T; Liu, L.T. Tetrahedron Lett. 1991, 32, 3795; Thaning, M.; Wistrand, L-G. J. Org. Chem. 1990, 55, 1406; Speckamp, W. M.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
38. 12. For recent reviews, see, Casiraghi, G.; Zanandi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677; Casiraghi, G.; Spanu, P. Synthesis, 1995, 607; see also Martin, S.F.; Barr, K.J. J. Am. Chem. Soc., 1996, 118, 3299; Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011; Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773; Martin, S. F; Corbett, J. W. Synthesis 1992, 55; Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G. Tetrahedron 1992, 48, 727; Harding, K. E; Coleman, M. T; Liu, L.T. Tetrahedron Lett. 1991, 32, 3795; Thaning, M.; Wistrand, L-G. J. Org. Chem. 1990, 55, 1406; Speckamp, W. M.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
39. 12. For recent reviews, see, Casiraghi, G.; Zanandi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677; Casiraghi, G.; Spanu, P. Synthesis, 1995, 607; see also Martin, S.F.; Barr, K.J. J. Am. Chem. Soc., 1996, 118, 3299; Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011; Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773; Martin, S. F; Corbett, J. W. Synthesis 1992, 55; Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G. Tetrahedron 1992, 48, 727; Harding, K. E; Coleman, M. T; Liu, L.T. Tetrahedron Lett. 1991, 32, 3795; Thaning, M.; Wistrand, L-G. J. Org. Chem. 1990, 55, 1406; Speckamp, W. M.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
40. 12. For recent reviews, see, Casiraghi, G.; Zanandi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677; Casiraghi, G.; Spanu, P. Synthesis, 1995, 607; see also Martin, S.F.; Barr, K.J. J. Am. Chem. Soc., 1996, 118, 3299; Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011; Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773; Martin, S. F; Corbett, J. W. Synthesis 1992, 55; Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G. Tetrahedron 1992, 48, 727; Harding, K. E; Coleman, M. T; Liu, L.T. Tetrahedron Lett. 1991, 32, 3795; Thaning, M.; Wistrand, L-G. J. Org. Chem. 1990, 55, 1406; Speckamp, W. M.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
41. 12. For recent reviews, see, Casiraghi, G.; Zanandi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677; Casiraghi, G.; Spanu, P. Synthesis, 1995, 607; see also Martin, S.F.; Barr, K.J. J. Am. Chem. Soc., 1996, 118, 3299; Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011; Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773; Martin, S. F; Corbett, J. W. Synthesis 1992, 55; Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G. Tetrahedron 1992, 48, 727; Harding, K. E; Coleman, M. T; Liu, L.T. Tetrahedron Lett. 1991, 32, 3795; Thaning, M.; Wistrand, L-G. J. Org. Chem. 1990, 55, 1406; Speckamp, W. M.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
42. 13. Modified procedure from Katoh, T.; Nagata, Y.; Kobayashi, Y.; Arai, K.; Minami, J.; Terashima, S. Tetrahedron Lett. 1993, 34, 5743.
43. 13C NMR), mass spectrometry (High resolution) and microanalytical methods. Optical rotations were recorded at 25 °C.
44. 15. Boeckman, R. K.; Potenza, J. C. Tetrahedron Lett. 1985, 26, 1411.
45. 16. Literature precedent see, Morimoto, Y.; Nishida, K.; Hayashi, Y. Tetrahedron Lett. 1993, 34, 5773.
46. 17. For a review, see, Mitsunobu, O. Synthesis 1981, 1; Hughes, D. L. Org React. 1992, 42, 335.
47. 17. For a review, see, Mitsunobu, O. Synthesis 1981, 1; Hughes, D. L. Org React. 1992, 42, 335.
48. 18. The Dess-Martin reagent was prepared as reported by; Ireland, R. E.; Longbin, L. J. Org. Chem. 1993, 8, 2899.
49. 19. Vishwakarma, L. C.; Stringer, O. D.; Davis, F. A. Org. Synth. 1988, 66, 203.
50. 20. Hartwig, W.; Born, L. J. Org. Chem. 1987, 52, 4352.
51. 21. Thompson, A. S.; Humphreys, G. R.; DeMarco, A. M.; Mathre, D. J.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 5886.
52. 22. Sajiki, H. Tetrahedron Lett. 1995, 36, 3465.
53. 23. Coste, J.; Campagne, J-M. Tetrahedron Lett. 1995, 36, 4253.
54. 24. For details of the NK binding assays, see Cascieri, M. A.; Ber, E.; Fong, T. M.; Sadowski, S.; Bansal, A.; Swain, C.; Seward, E.; Frances, B.; Burns, D.; Strader, C. D. Mol Pharmacol. 1992, 42, 458.