Structural studies of cytotoxic marine alkaloids: Synthesis of novel ring-E analogues of ascididemin and their in vitro and in vivo biological evaluation

Tetrahedron

Volumn 56, Issue 3, 2000, Pages 497-505

  Lindsay, Brent S ^a   Christiansen, Holly C ^a   Copp, Brent R ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Alkaloids; Antitumour compounds; Marine metabolites; Structure activity

Indexed keywords

ALKALOID; ASCIDIDEMIN; CYTOTOXIC AGENT; DNA TOPOISOMERASE; PYRIDINE DERIVATIVE;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; SOLID TUMOR; STRUCTURE ACTIVITY RELATION; TARGET CELL; XENOGRAFT;

EID: 0034645771     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01038-8     Document Type: Article

References (48)

1. (a) Molinski, T. F. Chem. Rev. 1993, 93, 1825-1838.
2. (b) Salomon, C. E.; Faulkner, D. J. Tetrahedron Lett. 1996, 37, 9147-9148.
3. (c) Plubrukarn, A.; Davidson, B. S. J. Org. Chem. 1998, 63, 1657-1659.
4. (d) Copp, B. R.; Jompa, J.; Tahir, A.; Ireland, C. M. J. Org. Chem. 1998, 63, 8024-8026.
5. (e) Eder, C.; Schupp, P.; Proksch, P.; Wray, V.; Steube, K.; Muller, C. E.; Frobenius, W.; Herderich, M.; van Soest, R. W. M. J. Nat. Prod. 1998, 61, 301-305.
6. (f) de Guzman, F. S.; Carte, B.; Troupe, N.; Faulkner, D. J.; Harper, M. K.; Concepcion, G. P.; Mangalindan, G. C.; Matsumoto, S. S.; Barrows, L. R.; Ireland, C. M. J. Org. Chem. 1999, 64, 1400-1402.
7. (a) Bloor, S. J.; Schmitz, F. J. J. Am. Chem. Soc. 1987, 109, 6134-6136.
8. (b) de Guzman, F. S.; Schmitz, F. J. Tetrahedron Lett. 1989, 30, 1069-1070.
9. (c) Lindsay, B. S.; Oliver, A. G.; Rickard, C. E. F.; Copp, B. R. J. Chem. Crystallogr. 1998, 28, 645-648.
10. Kobayashi, J.; Cheng, J.-F.; Nakamura, H.; Ohizumi, Y.; Hirata, Y.; Sasaki, T.; Ohta, T.; Nozoe, S. Tetrahedron Lett. 1988, 29, 1177-1180.
11. Schmitz, F. J.; De Guzman, F. S.; Hossain, M. B.; van der Helm, D. J. Org. Chem. 1991, 56, 804-808.
12. Zeng, C. M.; Ishibashi, M.; Matsumoto, K.; Nakaike, S.; Kobayashi, J. Tetrahedron 1993, 49, 8337-8342.
13. Carroll, A. R.; Scheuer, P. J. J. Org. Chem. 1990, 55, 4426-4431.
14. (a) Bracher, F. Liebigs Ann. Chem. 1990, 205-206.
15. (b) Bracher, F. Heterocycles 1989, 29, 2093-2095.
16. (c) Moody, C. J.; Rees, C. W.; Thomas, R. Tetrahedron Lett. 1990, 31, 4375-4376.
17. (d) Gomez-Bengoa, E.; Eschavarren, A. M. J. Org. Chem. 1991, 56, 3497-3501.
18. (e) Moody, C. J.; Rees, C. W.; Thomas, R. Tetrahedron 1992, 48, 3589-3602.
19. (f) Bracher, F. Liebigs Ann. Chem. 1992, 1205-1207.
20. (g) Kitahara, Y.; Nakahara, S.; Yonezawa, T.; Nagatsu, M.; Kubo, A. Heterocycles 1993, 36, 943-946.
21. (h) Gellerman, G.; Rudi, A.; Kashman, Y. Synthesis 1994, 3, 239-241.
22. (i) Kitahara, Y.; Tamura, F.; Kubo, A. Chem. Pharm. Bull. 1994, 42, 1363-1364.
23. (j) Lindsay, B. S.; Pearce, A. N.; Copp, B. R. Synth. Commun. 1997, 27, 2587-2592.
24. (k) Kitahara, Y.; Nakahara, S.; Yonezawa, T.; Nagatsu, M.; Shibano, Y.; Kubo, A. Tetrahedron 1997, 53, 17029-17038.
25. (l) Bontemps, N.; Delfourne, E.; Bastide, J.; Francisco, C.; Bracher, F. Tetrahedron 1997, 53, 1743-1750.
26. (m) Copp, B. R.; Hansen, R. P.; Appleton, D. R.; Lindsay, B. S.; Squire, C. J.; Clark, G. R.; Rickard, C. E. F. Synth. Commun. 1999, 29, 2665-2676.
27. (a) Bonnard, I.; Bontemps, N.; Lahmy, S.; Banaigs, B.; Combaut, G.; Francisco, C.; Colson, P.; Houssier, C.; Waring, M. J.; Bailly, C. Anti-Cancer Drug Des. 1995, 10, 333-346.
28. (b) Lindsay, B. S.; Barrows, L. R.; Copp, B. R. Bioorg. Med. Chem. Lett. 1995, 5, 739-742.
29. (c) Bracher, F. Pharmazie 1997, 52, 57-60.
30. (d) Blanco, M. D.; de la Fuente, J. A.; Avendano, C.; Menendez, J. C. Tetrahedron Lett. 1999, 40, 4097-4098.
31. Schmitz, F. J.; de Guzman, F. S.; Choi, Y.-H.; Hossain, M. B.; Rizvi, S. K.; van der Helm, D. Pure Appl. Chem. 1990, 62, 1393-1396.
32. Brederick, H.; Simchen, G.; Wahl, R. Chem. Ber. 1968, 101, 4048-4056.
33. Peterson, J. R.; Zjawiony, J. K.; Liu, S.; Hufford, C. D.; Clark, A. M.; Rogers, R. D. J. Med. Chem. 1992, 35, 4069-4077.
34. Krapcho, A. P.; Petry, M. E.; Getahun, Z.; Landi, J. J.; Stallman, J.; Polsenberg, J. F.; Gallagher, C. E.; Maresch, M. J.; Hacker, M. P. J. Med. Chem. 1994, 37, 828-837.
35. Enamine 7 and amine 20 had no detectable activity towards HIV-1 in testing at the NCI (data not shown).
36. Albert, A. Selective Toxicity, 7; Chapman & Hall: New York, 1985.
37. (a) Copp, B. R.; Fulton, K. F.; Perry, N. B.; Blunt, J. W.; Munro, M. H. G. J. Org. Chem. 1994, 59, 8233-8238.
38. (b) Boyd, M. R. Status of the NCI preclinical antitumor discovery screen: implications for section of new agents for clinical trial. In Cancer. Principles & Practise of Oncology; DeVita Jr., V. T., Hellman, S., Rosenberg, S. A., Eds.; Lippincott: Philadelphia, 1989; Vol. 3(10), pp 1-12.
39. (c) Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K. D.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; Gray-Goodrich, M.; Campbell, H.; Boyd, M. R. J. Natl. Cancer Inst. 1991, 83, 757-766.
40. (d) Boyd, M. R. In Current Therapy in Oncology; Neiderhuber, J. E., Ed.; Decker: Philadelphia, 1992; pp 11-22.
41. (e) Boyd, M. R.; Paul, K. D.; Rubenstein, L. R. In Antitumor Drug Discovery and Development; Valeriote, F. A., Corbett, T., Baker, L., Eds.; Kluwer Academic: Amsterdam, 1991; pp 11-34.
42. (f) Plowman, J.; Dykes, D. J.; Hollingshead, M.; Simpson-Herren, L.; Alley, M. C. In Anticancer Drug Development Guide: Preclinical Screening, Clinical trials and Approval; Teicher, B. Ed.; Humana Press: Totowa, NJ, 1997; pp 101-125.
43. Mean graphs depicting the dose-response data for compounds submitted to the NCI can be viewed online, by searching for the NSC number of the compound at the NCI web site http://dtp.nci.nih.gov/docs/cancer/searches/cancer_open_compounds. html
44. Paull, K. D.; Shoemaker, R. H.; Hodes, L.; Monks, A.; Scudiero, D. A.; Rubinstein, L.; Plowman, J.; Boyd, M. R. J. Natl. Cancer Inst. 1989, 81, 1088-1092.
45. Bachur, N.; Gordon, S. L.; Gee, M. V. Cancer Res. 1978, 38, 1745-1750.
46. Matsumoto, S. S.; Copp, B. R.; Holden, J. A.; Barrows, L.R. Unique DNA cleaving ability of novel ascididemin analogs through redox cycling and the production of reactive oxygen species. Poster presentation (P1942) at the 37th Annual meeting of the Society of Toxicology, Seattle, Washington, 1-5 March 1998.
47. Xenograft assay treatment schedules: MDA-MB-435 and -231 Q4D×3, 13 (i.e. every four days for a total of three treatments with the first treatment given on day 13 after tumour implantation). LOX IMVI QD×5, 8. OVCAR-3 Q4D×3, 6. U251 Q4D×3, 14. HCT-116 QD×5, 9. NCI-H460 QD×5, 2. NCI-H522 QD×5, 7. SF-295 QD×5, 2. UACC Q4D×3, 15.
48. Bracher, F. Liebigs Ann. Chem. 1989, 87.