Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1

Journal of Natural Products

Volumn 68, Issue 2, 2005, Pages 207-211

  Pettit, George R ^a   Melody, Noeleen ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 DEOXYDIHYDRONARCISTATIN; 7 DEOXYNARCISTATIN; ANTINEOPLASTIC AGENT; DIHYDRONARCISTATIN 1; HYMENOCALLIS LITTORALIS EXTRACT; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYMENOCALLIS LITTORALIS; MEDICINAL PLANT; MOUSE; NONHUMAN; PLANT BULB; REACTION ANALYSIS; REDUCTION;

AMARYLLIDACEAE ALKALOIDS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HUMANS; LILIACEAE; MOLECULAR STRUCTURE; PHENANTHRIDINES; PLANTS, MEDICINAL;

EID: 14544298394     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0304518     Document Type: Article

References (37)

1. For series part 526, refer to: Kirwan, I. G.; Loadman, P. M.; Swaine, D. J.; Anthoney, D. A.; Pettit, G. R.; Lippert, J. W., III; Shnyder, S. D.; Cooper, P. A.; Bibby, M. C. Clin. Cancer Res., accepted.
2. (a) Dieckmann, W.; Meiser, W. Chem. Inst., R. Bav. Acad. Sci., Munich, Ber. 1909, 41, 3253-3269.
3. (b) Bain, D.; Perkin, W. H., Jr.; Robinson, R. J. Chem. Soc. 1914, 105, 2392-2404.
4. (c) Chichibabin, A. E.; Oparina, M. P. J. Russ. Phys.-Chem. Soc. 1920, 50, 543-548.
5. (a) Fitzgerald, D. B.; Hartwell, J. L.; Leiter, J. J. Natl. Cancer Inst. 1958, 20, 763-764.
6. (b) Ceriotti, G. Nature (London) 1987, 213, 595-596.
7. Krohn, K.; Mondon, A. Chem. Ber. 1976, 109, 855-876.
8. Selman, A.; de la Torre, C. Experientia 1878, 34, 1455-1457.
9. Carrasco, L.; Fresno, M.; Vazquez, D. FEBS Lett. 1975, 52, 236-239.
10. Baez, A.; Vazquez, D. Biochim. Biophys. Acta 1878, 518, 95-103.
11. Suffhess, M.; Cordell, G. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; pp 205-207.
12. (a) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M. J. Nat. Prod. 1984, 47, 1018-1020.
13. (b) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1984, 1693-1694.
14. (c) Pettit, G. R.; Gaddamidi, V.; Herald, D. L.; Singh, S. B.; Cragg, G. M.; Schmidt, J. M. J. Nat. Prod. 1988, 49, 995-1002.
15. (a) Pettit, G. R.; Pettit, G. R., III; Backhaus, R. A.; Boyd, M. R.; Meerow, A. W. J. Nat. Prod. 1993, 56, 1682-1687.
16. (b) Pettit, G. R.; Pettit, G. R., III; Groszek, G.; Backhaus, R. A.; Doubek, D. L.; Barr, R. J.; Meerow, A. W. J. Nat. Prod. 1995, 58, 756-759.
17. (c) Pettit, G. R.; Pettit, G. R., III; Backhaus, R. A.; Boettner, P. E. J. Nat. Prod. 1995, 58, 37-43.
18. (a) Backhaus, R. A.; Pettit, G. R., III; Huang, D. S.; Pettit, G. R.; Groszek, G.; Odgers, J. C.; Ho, J.; Meerow, A. Acta Horticulturae 1992, 364-366.
19. (b) Pettit, G. R.; Pettit, G. R., III; Groszek, G.; Backhaus, R. A.; Doubek, D. L.; Barr, R. J.; Meerow, A. J. Nat. Prod. 1995, 58, 756-759.
20. (a) Pettit, G. R.; Melody, N.; Herald, D. L. J. Org. Chem. 2001, 66, 2583-2587.
21. (b) McNulty, J.; Mao, J.; Gibe, R.; Mo, R.; Wolf, S.; Pettit, G. R.; Herald, D. L.; Boyd, M. R. BioOrg. Med. Chem. Lett. 2001, 11, 169-172.
22. (c) Pettit, G. R.; Melody, N.; Herald, D. L.; Schmidt, J. M.; Pettit, R. K.; Chapuis, J.-C. Heterocycles 2002, 56, 139-155.
23. (d) Pettit, G. R.; Melody, N.; O'Sullivan, M.; Thompson, M. A.; Herald, D. L.; Coates, B. J. Chem. Soc., Chem. Commun. 1994, 2725-2726.
24. (a) Pettit, G. R.; Melody, N.; Simpson, M.; Thompson, M.; Herald, D. L.; Knight, J. J. Nat. Prod. 2003, 66, 92-96.
25. (b) Pettit, G. R.; Orr, B.; Ducki, S. Anti-Cancer Drug Des. 2000, 15, 389-395.
26. (c) Pettit, G. R.; Freeman, S.; Simpson, M. J.; Thompson, M. A.; Boyd, M. R.; Williams, M. D.; Pettit, G. R., III; Doubek, D. L. Anti-Cancer Drug Des. 1995, 10, 243-250.
27. Hudlicky, T.; Rinner, U.; Gonzalez, D.; Akgun, H.; Schilling, S.; Siengalewicz, P.; Martinot, T. A.; Pettit, G. R. J. Org. Chem. 2002, 67, 8726-8743.
28. (a) Gabrielsen, B.; Monath, T. P.; Huggins, J. W.; Kefauver, D. F.; Pettit, G. R.; Groszek, G.; Hollingshead, M.; Kirsi, J. J.; Shannon, W. M.; Schubert, E. M.; Dare, J.; Ugarkar, B.; Ussery, M. A.; Phelan, M. J. J. Nat. Prod. 1992, 55, 1569-1581.
29. (b) Bibby, M. C.; Holwell, S. E.; Pettit, G. R. Anti-Vascular and Antitumor Effects of the Novel Agent Pancratistatin Phosphate. Abstract. Biological Basis for Antiangiogenic Therapy Conference, Milan, Italy, Nov 8-10, 1999.
30. (a) Dowlati, A.; Robertson, K.; Cooney, M.; Petros, W. P.; Stratford, M.; Jesberger, J.; Rafie, N.; Overmoyer, B.; Makkar, V.; Stambler, B.; Taylor, A.; Waas, J.; Lewin, J. S.; McCrae, K. R.; Remick, S. C. Cancer Res. 2002, 62, 3408-3416.
31. (b) Dziba, J. M.; Marcinek, R.; Venkataraman, G.; Robinson, J. A.; Ain, K. B. Thyroid 2002, 12, 1063-1070.
32. (c) Eikesdal, H. P.; Landuyt, W.; Dahl, O. Cancer Lett. 2002, 178, 209-217.
33. (d) Prise, V.; Honess, D. J.; Stratford, M. R. L.; Wilson, J.; Tozer, G. M. Int. J. Oncol. 2002, 21, 717-726.
34. (e) Hill, S. A.; Chaplin, D. J.; Lewis, G.; Tozer, G. M. Int. J. Cancer 2002, 102, 70-74.
35. Pettit, G. R.; Melody, N.; Herald, D. L. J. Nat. Prod., in press.
36. trans-Dihydronarciclasine was synthesized by our group in 1992 from narciclasine according to procedures described by Mondon and Krohn.19
37. Mondon, A.; Krohn, K. Chem. Ber. 1975, 108, 445-463.