Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine

Journal of Natural Products

Volumn 69, Issue 1, 2006, Pages 7-13

  Pettit, George R ^a   Eastham, Stephen A ^a   Melody, Noeleen ^a   Orr, Brian ^a   Herald, Delbert L ^a   McGregor, Jane ^a   Knight, John C ^a   Doubek, Dennis L ^a   Pettit III, George R ^a   Garner, Lynnette C ^a   Bell, Joy A ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 ACETONIDE 5 AZA 6 DEOXYNARCICLASINE; 5 AZA 6 DEOXYDIHYDRONARCICLASINE; 5 AZA 6 DEOXYNARCICLASINE; 7 DEOXYDIHYDRONARCICLASINE; 7 DEOXYNARCICLASINE; ALCOHOL DERIVATIVE; ALUMINUM; ALUMINUM LITHIUM HYDRIDE; ANTINEOPLASTIC AGENT; ESTER; HYDROGEN SULFIDE; HYMENOCALLIS LITTORALIS EXTRACT; ISOCARBOSTYRIL DERIVATIVE; LITHIUM; NARCICLASINE; NATURAL PRODUCT; PANCRATISTATIN; PLANT EXTRACT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; CANCER CELL; CANCER CELL CULTURE; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN MCF 7; CRYSTAL STRUCTURE; CULTURE MEDIUM; DRUG EFFICACY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; HYMENOCALLIS LITTORALIS; LEUKEMIA CELL; LYMPHATIC LEUKEMIA; MEDICINAL PLANT; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

AMARYLLIDACEAE ALKALOIDS; ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; ISOQUINOLINES; LEUKEMIA P388; MICE; MOLECULAR STRUCTURE; NARCISSUS; PLANTS, MEDICINAL; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA; HYMENOCALLIS LITTORALIS; MINK CELL FOCUS-FORMING VIRUS; MURINAE;

EID: 32644435896     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np058068l     Document Type: Article

References (37)

1. Antineoplastic Agents. 457. For Series Part 456, refer to: Mohammad, R. M.; Li, Y.; Mohamed, A. N.; Pettit, G. R.; Adsay, V.; Vaitkevicius, V. K.; Al-Katib, A. M.; Sarkar, F. H. Pancreas 1999, 19, 353-361.
2. For leading references consult: Hartwell, J. L. Plants Used Against Cancer; Quarterman Publications: Lawrence, MA, 1982.
3. Duke, J. A.; Duke, P. K. Medicinal Plants of the Bible; Trad-Medic Books: New York, 1983; p 98.
4. (a) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1984, 1693-1694.
5. (b) Pettit, G. R.; Gaddamidi, V.; Herald, D. L.; Singh, S. B.; Cragg, G. M.; Schmidt, J. M.; Boettner, F. E.; Williams, M.; Sagawa, Y. J. Nat. Prod. 1986, 49, 995-1002.
6. (c) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M. J. Nat. Prod. 1984, 47, 1018-1020.
7. (d) Pettit, G. R.; Cragg, G. M.; Singh, S. B.; Duke, J. A.; Doubek, D. L. J. Nat. Prod. 1990, 53, 176-178.
8. (e) Pettit, G. R.; Pettit, G. R., III; Backhaus, R. A.; Boettner, F. E. J. Nat. Prod. 1995,58, 37-43.
9. (f) 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.
10. (g) Pettit, G. R.; Pettit, G. R., III; Backhaus, R. A.; Boyd, M. R.; Meerow, A. W. J. Nat. Prod. 1993, 56, 1682-1687.
11. (a) 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.
12. (b) Ceretti, G. Nature 1967, 213, 595.
13. Okamoto, T.; Torii, Y.; Isogain, Y. Chem. Pharm. Bull. 1968, 16, 1860.
14. Kojima, K.; Mutsuga, M.; Inoue, M.; Ogihara, Y. Phytochemistry 1998, 48, 1199-1202.
15. For a leading reference, see: (a) Pettit, G. R.; Melody, N.; Herald, D. L. J. Nat. Prod. 2004, 67, 322-327.
16. For a recent summary, see: (b) Magnus, P.; Sebhat, I. K. Tetrahedron 1998, 54, 15509-15524.
17. (a) Pettit, G. R.; Orr, B.; Ducki, S. Anti-Cancer Drug Des. 2000, 15, 389-395.
18. (b) 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.
19. (c) Gabrielsen, B.; Monath, T. P.; Muggins, 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.
20. (d) Gabrielsen, B.; Monath, T. P.; Huggins, J. W.; Kirsi, J. J.; Hollingshead, M.; Shannon, W. M.; Pettit, G. R. In Natural Products as Antiviral Agents; Chu, C. K., Ed.; Plenum Press: New York, 1992; pp 121-135.
21. Ouarzane-Amara, M.; Franetich, J.-F.; Mazier, D.; Pettit, G. R.; Meijer, L.; Doerig, C.; Desportes-Livage, I. Antimicrob. Agents Chemother. 2001, 45, 3409-3415.
22. (a) Pettit, G. R.; Ducki, S. Eastham, S.; Melody, N. Oncol. Res., in press,
23. (b) Rinner, U.; Hillebrenner, H. L.; Adams, D. R.; Hudlicky, T.; Pettit, G. R. Bioorg. Med. Chem. Lett. 2004, 14, 2911-2915.
24. (c) 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.
25. Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367.
26. Banwell, M. G.; Cowden, C. J.; Gable, R. W. J. Chem. Soc., Perkin Trans, 1 1994, 3515-3518.
27. Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535-556.
28. Isobe, K.; Taga, J.; Tsuda, Y. Heterocycles 1978, 9, 625-630.
29. Pettit, G. R.; Melody, N.; O'Sullivan, M.; Thompson, M. A.; Herald, D. L.; Coates, B. J. Chem. Soc., Chem. Commun. 1994, 2725-2726.
30. XPREP-The automatic space group determination program in SHELXTL (see ref 16).
31. North, A. C.; Phillips, D. C.; Mathews, F. S, Acta Crystallogr. 1968 A2, 351.
32. SHELXTL-PC Version 5.1, an integrated software system for the determination of crystal structures from diffraction data; Bruker Analytical X-ray Systems, Inc.: Madison, WI, 1997. This package includes, among others: XPREP, an automatic space group determination program; XS, the Bruker SHELXS module for the solution of X-ray crystal structures from diffraction data; XL, the Bruker SHELXL module for structure refinement; XP, the Bruker interactive graphics display module for crystal structures.
33. Flack, H. D.; Bernardinelli, G. J. Appl. Crystallogr. 2000, 33, 1143-1148.
34. (a) Keck, G. E.; Wagner, T. T.; Felix, D. R. J. Am. Chem. Soc. 1999, 121, 5176-5190.
35. (b) Krohn, K.; Mondon, A. Chem. Ber. 1976, 109, 855-876.
36. Blessing, R. Acta Crystallogr. 1995, A51, 33-8.
37. Crystallographic data for the structures reported in this paper have been deposited as CEF files with the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 156787, 156788, and 156789. Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0) 223-336033 or e-mail: deposit@ccdc.cam.ac.uk].