Solid Phase Syntheses of Polyamine Toxins HO-416b and PhTX-433. Use of an Efficient Polyamide Reduction Strategy That Facilitates Access to Branched Analogues

Organic Letters

Volumn 2, Issue 11, 2000, Pages 1581-1583

  Wang, Fan ^a   Manku, Sukhdev ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DELTA-PHILANTHOTOXIN; HO 416B; INDOLE DERIVATIVE; NEUROTOXIN; NICOTINIC RECEPTOR BLOCKING AGENT; PHILANTHOTOXIN; POLYAMINE; SPIDER VENOM; WASP VENOM;

ARTICLE; CHEMISTRY; SYNTHESIS;

INDOLES; NEUROTOXINS; NICOTINIC ANTAGONISTS; POLYAMINES; SPIDER VENOMS; WASP VENOMS;

EID: 0034199961     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005817b     Document Type: Article

References (22)

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4. For a selection of recent reports on the synthesis of philanthotoxin analogues, see: (a) Strømgaard, K.; Brierley, 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, 5224-5234. (b) Rosini, M.; Budriesi, R.; Bixel, M. G.; Bolognesi, M. L.; Chiarini, A.; Hucho, F.; Krogsgaard-Larsen, P.; Mellor, I. R.; Minarini, A.; Tumiatti, V.; Usherwood, P. N. R.; Melchiorre, C. J. Med. Chem. 1999, 42, 5212-5223. (c) Nakanishi, K.; Huang, X.; Jiang, H.; Liu, Y.; Fang, K.; Huang, D.; Choi, S.-K.; Katz, E.; Eldefrawi, M. Bioorg. Med. Chem. Lett. 1997, 5, 11969-1988. (d) Huang, D.; Jiang, H.; Nakanishi, K.; Usherwood, P. N. R. Tetrahedron 1997, 53, 12391-12404.
5. For a selection of recent reports on the synthesis of philanthotoxin analogues, see: (a) Strømgaard, K.; Brierley, 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, 5224-5234. (b) Rosini, M.; Budriesi, R.; Bixel, M. G.; Bolognesi, M. L.; Chiarini, A.; Hucho, F.; Krogsgaard-Larsen, P.; Mellor, I. R.; Minarini, A.; Tumiatti, V.; Usherwood, P. N. R.; Melchiorre, C. J. Med. Chem. 1999, 42, 5212-5223. (c) Nakanishi, K.; Huang, X.; Jiang, H.; Liu, Y.; Fang, K.; Huang, D.; Choi, S.-K.; Katz, E.; Eldefrawi, M. Bioorg. Med. Chem. Lett. 1997, 5, 11969-1988. (d) Huang, D.; Jiang, H.; Nakanishi, K.; Usherwood, P. N. R. Tetrahedron 1997, 53, 12391-12404.
6. For a selection of recent reports on the synthesis of philanthotoxin analogues, see: (a) Strømgaard, K.; Brierley, 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, 5224-5234. (b) Rosini, M.; Budriesi, R.; Bixel, M. G.; Bolognesi, M. L.; Chiarini, A.; Hucho, F.; Krogsgaard-Larsen, P.; Mellor, I. R.; Minarini, A.; Tumiatti, V.; Usherwood, P. N. R.; Melchiorre, C. J. Med. Chem. 1999, 42, 5212-5223. (c) Nakanishi, K.; Huang, X.; Jiang, H.; Liu, Y.; Fang, K.; Huang, D.; Choi, S.-K.; Katz, E.; Eldefrawi, M. Bioorg. Med. Chem. Lett. 1997, 5, 11969-1988. (d) Huang, D.; Jiang, H.; Nakanishi, K.; Usherwood, P. N. R. Tetrahedron 1997, 53, 12391-12404.
7. For a selection of recent reports on the synthesis of philanthotoxin analogues, see: (a) Strømgaard, K.; Brierley, 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, 5224-5234. (b) Rosini, M.; Budriesi, R.; Bixel, M. G.; Bolognesi, M. L.; Chiarini, A.; Hucho, F.; Krogsgaard-Larsen, P.; Mellor, I. R.; Minarini, A.; Tumiatti, V.; Usherwood, P. N. R.; Melchiorre, C. J. Med. Chem. 1999, 42, 5212-5223. (c) Nakanishi, K.; Huang, X.; Jiang, H.; Liu, Y.; Fang, K.; Huang, D.; Choi, S.-K.; Katz, E.; Eldefrawi, M. Bioorg. Med. Chem. Lett. 1997, 5, 11969-1988. (d) Huang, D.; Jiang, H.; Nakanishi, K.; Usherwood, P. N. R. Tetrahedron 1997, 53, 12391-12404.
8. For a recent report involving PhTX-343, see: Bähring, R.; Mayer, M. L. J. Physiol. 1998, 509, 635-650.
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10. For reviews on the pharmacology of polyamines, see: (a) Mueller, A. L.; Roeloffs, R.; Jackson, H. The Alkaloids; Academic Press: New York, 1995; Vol. 46, Chapt. 2, pp 63-94. (b) Carter, C., Ed. The Neuropharmacology of Polyamines; Academic Press: San Diego, 1994.
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13. HO-416b (1): (a) Hidai, Y.; Kan, T.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 4711-4714. PhTX-433 (2): (b) Piek, T.; Fokkens, R. H.; Karst, H.; Kruk, C.; Lind, A.; van Marie, J.; Nakajima, T.; Nibbering, N. M. M.; Shinozaki, H.; Spanier, W.; Tong, Y. C. In Neurotox '88L Molecular Basis of Drug and Pesticide Action; 1988; Abstract, p 61. (c) Reference 2.
14. HO-416b (1): (a) Hidai, Y.; Kan, T.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 4711-4714. PhTX-433 (2): (b) Piek, T.; Fokkens, R. H.; Karst, H.; Kruk, C.; Lind, A.; van Marie, J.; Nakajima, T.; Nibbering, N. M. M.; Shinozaki, H.; Spanier, W.; Tong, Y. C. In Neurotox '88L Molecular Basis of Drug and Pesticide Action; 1988; Abstract, p 61. (c) Reference 2.
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20. NMR and MS data are fully consistent with the assigned structures (see Supporting Information). RP-HPLC analyses were performed on a Zorbax SB-C18 column (4.6 x 150 mm, 5 μm) using 0.1% TFA water/ acetonitrile mobile phases and UV detection. Should higher homogeneity be required toward biological testing, products could be further purified by semipreparative HPLC.
21. Another solid-supported synthesis of PhTX-433 was recently reported. See: Chhabra, S. R.; Khan, A. N.; Bycroft, B. W. Tetrahedron Lett. 2000, 41, 1099-1102.
22. This borane reduction protocol was shown to be racemization free (see ref 12).