A versatile method for solid-phase synthesis of polyamines: Neuroactive polyamine toxins as example

Synthesis

Volumn , Issue 6, 2001, Pages 877-884

  Strømgaard, Kristian ^a   Andersen, Kim ^b   Ruhland, Thomas ^b   Krogsgaard Larsen, Povl ^a   Jaroszewski, Jerzy W ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b H LUNDBECK A S   (Denmark)

Author keywords

Amines; Mitsunobu reaction; Parallel synthesis; Philanthotoxins; Solidphase synthesis

Indexed keywords

ALCOHOLS; ALKYLATION; SYNTHESIS (CHEMICAL); TOXIC MATERIALS;

SOLID-PHASE SYNTHESIS;

AMINES;

AMINOALCOHOL; CYCLOBUTANE; CYCLOPROPANE; NEUROTOXIN; NITROBENZENE DERIVATIVE; NITROGEN; PHILANTHOTOXIN; PHOSPHINE DERIVATIVE; PIPERIDINE DERIVATIVE; POLYAMINE; WASP VENOM;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); IMMOBILIZATION; REACTION TIME; TEMPERATURE; TOXIN SYNTHESIS;

EID: 0001825873     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2001-13410     Document Type: Article

References (76)

1. Geneste, H.; Hesse, M. Chem. Unserer Zeit 1998, 32, 206.
2. Seiler, N.; Atanassov, C. L.; Raul, F. Int. J. Oncol. 1998, 13, 993.
3. Frydman, B.; Aldonia, V. Expert Opin. Ther. Pat. 1999, 9, 1055.
4. Davidson, N. E.; Hahm, H. A.; McCloskey, D. E.; Woster, P. M.; Casero, R. A. Jr.;. Endocr. Relat. Cancer 1999, 6, 69.
5. Hamana, K.; Matsuzaki, S. Crit. Rev. Microbiol. 1992, 18, 261.
6. Hamana, K.; Hamana, H.; Shinozawa, T.; Niitsu, M.; Samajama, K.; Itoh, T. Microbios 1999, 97, 117.
7. Savage, P. B.; Li, C. Expert Opin. Invest. Drugs 2000, 9, 263.
8. Hecht, S. M. J. Nat. Prod. 2000, 63, 158.
9. Guggisberg, A.; Hesse, M. Alkaloids 1983, 22, 85.
10. Guggisberg, A.; Hesse, M. Alkaloids 1998, 50, 219.
11. McCormick, K. D.; Meinwald, J. J. Chem. Ecol. 1993, 19, 2411.
12. Schäfer, A.; Benz, H.; Fiedler, W.; Guggisberg, A.; Bienz, S.; Hesse, M. Alkaloids 1994, 45, 1.
13. Mueller, A.; Roeloffs, R.; Jackson, H. Alkaloids 1995, 46, 63.
14. The Neuropharmacology of Polyamines Carter, C., Ed.; Academic Press: London, 1994.
15. Strømgaard, K.; Brierly, M. J.; Andersen, K.; Sløk, F. A.; Mellor, I. R.; Usherwood, P. N. R.; Krogsgaard-Larsen, P.; Jaroszewski, J. W. J. Med. Chem. 1999, 42, 5224.
16. Strømgaard, K.; Bjørnsdottir, I.; Andersen, K.; Brierly, M.; Rizoli, S.; Eldursi, N.; Mellor, I. R.; Usherwood, P. N. R.; Hansen, S. H.; Krogsgaard-Larsen, P.; Jaroszewski, J. W. Chirality 2000, 12, 93.
17. Strømgaard, K.; Brier, T. J.; Andersen, K.; Mellor, I. R.; Saghyan, A.; Tikhonov, D.; Usherwood, P. N. R.; Krogsgaard-Larsen, P.; Jaroszewski, J. W. J. Med. Chem. 2000, 43, 4526.
18. Walker, S.; Sofia, M. J.; Axelrod, H. R. Adv. Drug Delivery Rev. 1998, 30, 61.
19. Duguid, J. G.; Durland, R. H. Drug Targeting Delivery 1999, 10, 45.
20. Bencini, A.; Bianchi, A.; Garcia-España, E.; Micheloni, M.; Ramirez, J. A. Coord. Chem. Rev. 1999, 188, 97.
21. Meijer, E. W. Adv. Dendritic Macromol. 1999, 4, 61.
22. Pak, J. K.; Guggisberg, A.; Hesse, M. Tetrahedron 1998, 54, 8035.
23. Pak, J. K.; Hesse, M. J. Org. Chem. 1998, 63, 8200.
24. Pak, J. K.; Hesse, M. Helv. Chim. Acta 1998, 81, 2300.
25. Kuksa, V.; Buchan, R.; Kong Thoo Lin, P. Synthesis 2000, 1189.
26. Bycroft, B. G.; Chan, W. C.; Hone, N. D.; Millington, S.; Nash, I. A. J. Am. Chem. Soc. 1994, 116, 7415.
27. Nash, I. A.; Bycroft, B. W.; Chan, W. C. Tetrahedron Lett. 1996, 37, 2625.
28. Page, P.; Burrage, S.; Baldock, L.; Bradley, M. Bioorg. Med. Chem. Lett. 1998, 8, 1751.
29. Ostrech, J. M.; Schoner, C. C.; Hamashin, V. T.; Nefzi, A.; Meyer, J. P.; Houghten, R. A. J. Org. Chem. 1998, 63, 8622.
30. Hall, D. G.; Laplante, C.; Manku, S.; Nagendran, J. J. Org. Chem. 1999, 64, 689.
31. Carrington, S.; Renault, J.; Tomasi, S.; Sinbandhit, S.; Blagbrough, I. S.; Uriac, P. Pharm. Pharmacol. Commun. 1999, 5, 151.
32. Chhabra, S. R.; Khan, A. N.; Bycroft, B. W. Tetrahedron Lett. 2000, 41, 1099.
33. Chhabra, S. R.; Khan, A. N.; Bycroft, B. W. Tetrahedron Lett. 2000, 41, 1095.
34. Wang, F.; Sukhdev, M.; Hall, D. G. Org. Lett. 2000, 2, 1581.
35. Fukuyama, T.; Jow, C. K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
36. Fukuyama, T.; Cheung, M.; Jow, C. K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831.
37. Mitsunobu, O. Synthesis 1981, 1.
38. Hughes, D. Org. React. 1992, 42, 335.
39. Dankwardt, M.; Smith, D. B.; Porco, J. A Jr.; Nguyen, C. H. Synlett 1997, 854.
40. Miller, S. C.; Scanlan, T. S. J. Am. Chem. Soc. 1997, 119, 2301.
41. Kay, C.; Murray, P. J.; Sandow, L.; Holmes, A. B. Tetrahedron Lett. 1997, 38, 6941.
42. Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143.
43. Yang, L.; Chiu, K. Tetrahedron Lett. 1997, 38, 7307.
44. Swayze, E. E. Tetrahedron Lett. 1997, 38, 8643.
45. Miller, S. C.; Scanlan, T. S. J. Am. Chem. Soc. 1998, 120, 2690.
46. Reichwein, J. F.; Liskamp, R. M. J. Tetrahedron Lett. 1998, 39, 1243.
47. Raman, P.; Stokes, S. S.; Angell, Y. M.; Flentke, G. R.; Rich, D. H. J. Org. Chem. 1998, 63, 5734.
48. Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron Lett. 1998, 39, 2667.
49. Boeijen, A.; Kruijtzer, J. A. W.; Liskamp, R. M. J. Bioorg. Med. Chem. Lett. 1998, 8, 2375.
50. Veerman, J. J. N.; van Maarseveen, J. H.; Visser, G. M.; Kruse, C. G.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 1998, 2583.
51. Scicinski, J. J.; Barker, M. D.; Murray, P. J.; Jarvie, E. M. Bioorg. Med. Chem. Lett. 1998, 8, 3609.
52. Mohamed, N.; Bhatt, U.; Just, G. Tetrahedron Lett. 1998, 39, 8213.
53. Bolton, G. L.; Hodges, J. C. J. Comb. Chem. 1999, 1, 130.
54. Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron 1999, 55, 8189.
55. Lin, X.; Dorr, H.; Nuss, J. M. Tetrahedron Lett. 2000, 41, 3309.
56. Davis, P. W.; Swayze, E. E. Biotechnol. Bioeng. 2000, 71, 19.
57. Eldefrawi, A. T.; Eldefrawi, M. E.; Konno, K.; Mansour, N. A.; Nakanishi, K.; Oltz, E.; Usherwood, P. N. R. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4910.
58. Carpino, L. A.; Tsao, J. H.; Ringsdorf, H.; Fell, E.; Hettrich, G. J. Chem. Soc., Chem. Commun. 1978, 358.
59. Rosowsky, A.; Wright, J. E. J. Org. Chem. 1983, 48, 1539.
60. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595.
61. Wuts, P. G. M.; Northuis, J. M. Tetrahedron Lett. 1998, 39, 3889.
62. Tsunoda, T.; Yamamiya, Y.; Itô, S. Tetrahedron Lett. 1993, 34, 1639.
63. Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519.
64. Larget, R.; Lockhart, B.; Renard, P.; Largeron, M. Bioorg. Med. Chem. Lett. 2000, 10, 835.
65. Kim, S. W.; Hong, C. Y.; Lee, K.; Lee, E. J.; Koh, J. S. Bioorg. Med. Chem. Lett. 1998, 8, 735.
66. Koh, J. S.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494.
67. Carpino, L. A.; El-Faham, A. J. Org. Chem. 1994, 59, 695.
68. Carpino, L. A.; Ionescu, D.; El-Faham, A. J. Org. Chem. 1996, 61, 2460.
69. Zeng, Z.; Burton, L.; Yung, K.; Shushan, B.; Kassel, D. B. J. Chromatogr., A 1998, 794, 3.
70. Hsu, B. H.; Orton, E.; Tang, S. Y.; Carlton, R. A. J. Chromatogr., B 1999, 725, 103.
71. Karigiannis, G.; Papaioannou, D. Eur. J. Org. Chem. 2000, 1841.
72. Hidai, Y.; Kan, T.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 4714.
73. Hidai, Y.; Kan, T.; Fukuyama, T. Chem. Pharm. Bull. 2000, 48, 1570.
74. Hone, N. D.; Payne, L. Tetrahedron Lett. 2000, 41, 6149.
75. Kita, Y.; Haruta, J. I.; Yasuda, H.; Fukunaga, K.; Shirouchi, Y.; Tamuta, Y. J. Org. Chem. 1982, 47, 2697.
76. Jaroszewski, J. W.; Matzen, L.; Frølund, B.; Krogsgaard-Larsen, P. J. Med. Chem. 1996, 39, 515.