Synthesis and antiproliferative activity of a cyclic analog of dolastatin 10

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 20, 1998, Pages 2855-2858

  Poncet, Joël ^a   Hortala, Laurent ^a   Busquet, Magali ^a   Guéritte Voegelein, Françoise ^b   Thoret, Sylvie ^b   Pierré, Alain ^c   Atassi, Ghanem ^c   Jouin, Patrick ^a  

^a Lab des Mecanismes M   (France)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^c INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

Antineoplastic; Antiproliferative agent; Depsipeptide; Marine metabolites

Indexed keywords

DOLASTATIN;

AMINO TERMINAL SEQUENCE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBOXY TERMINAL SEQUENCE; CELL GROWTH; CELL PROLIFERATION; DRUG SYNTHESIS; GROWTH INHIBITION; MICROTUBULE ASSEMBLY; MOLECULAR INTERACTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOPOLYMERS; CYCLIZATION; DRUG SCREENING ASSAYS, ANTITUMOR; HT29 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; LEUKEMIA L1210; MICE; OLIGOPEPTIDES; TUBULIN MODULATORS;

EID: 0032552916     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00511-3     Document Type: Article

References (21)

1. 1. Pettit, G. R.; Xu, J.P.; Williams, F. H.; Schmidt, J. M.; Cerny, R. L. Bioorg. Med. Chem. Lett. 1997 ,7 , 827.
2. 2. Sone, H.; Kigoshi, H.; Yamada, K.; Tetrahedron 1991,53 ,8149.
3. 3. Pettit, G. R. The dolastatins. In Progress in the Chemistry of Organic Natural Products; Herz, W.; Kirby, G. W.; More, R. E.; Steglich, W.; Tamm, C., Eds.; Springer-Verlag: Vienna, 1997; Vol. 70 , pp 1-79.
4. 4. Kobayashi, M.; Natsume, T.; Tamaoki, S.; Watanabe, J.; Asano, H.; Mikami, T.; Miyasaka, K.; Miyazaki, K.; Gondo, M.; Sakakibara, K.; Tsukahoshi, S. Jpn. J. Cancer Res. 1997, 88, 316.
5. 5. Bai, R.; Taylor, G. F.; Schmidt, J. M.; Williams, M. D.; Kepler, J. A.; Pettit, G. R.; Hamel, E. Mol. Pharmacol. 1995, 47, 965.
6. 6. Alattia, T.; Roux F.; Poncet, J.; Cavé, A.; Jouin, P. Tetrahedron 1995, 51, 2593.
7. 7. Pettit, G. R.; Srirangam, J. K. Herald, D. L.; Hamel, E. J. Org. Chem. 1994, 59, 6127.
8. 8..Benedetti, E.; Carlomagno, T.; Fraternali, F.; Hamada, Y.; Hayashi, K.; Paotillo, L.; Shioiri, T. Biopolymers 1995, 35, 525.
9. 9. Fantucci, P.; Marino, T.; Russo, N.; Villa, A. M. J. Comput. Mol. Des. 1995, 9, 425.
10. 10. Bowman, R. E.; Stroud, H. H. J. Chem. Soc. 1950, 1342.
11. 11. Hamada, Y.; Shibata, M.; Kato, S.; Shioiri, T. J. Org. Chem. 1987, 52, 1252.
12. 12. Roux, F.; Maugras, I.; Poncet, J.; Niel, G.; Jouin, P. Tetrahedron 1994, 50, 5345.
13. 13. Zeggaf, C.; Poncet, J.; Jouin, P.; Dufour, M-N.; Castro, B. Tetrahedron 1989, 45, 5039.
14. R = 3.04 min
15. m = 18.9 min for dolastatin 10.
16. 16. Reeves Huie, W.; Newman, R. A.; Hutto, T.; Madden, T. J. Chromato. B 1997, 693, 451.
17. 17. MS (FAB) m/z (%) 813 (M+H+, 85), 781 (M-MeOH+H+, 10); HRMS (FAB) calcd for C42H65N6O8S 813.4585, found 813.4583.
18. 18. Bai, R.; Pettit, G. R.; Hamel, E. Biochem. Pharmacol. 1990, 40, 1859.
19. 19. Miyazaki, K.; Kobayashi, M.; Natsume, T.; Gondo, M.; Mikami, T.; Sakakibara, K.; Tsukagoshi, S. Chem. Pharm. Bull. 1995, 43, 1706.
20. 20. Poncet, J.; Busquet, M.; Roux, F.; Pierré, A.; Atassi, G.; Jouin, P. J. Med. Chem. 1998, 41, 1524.
21. 21. Pettit, G. R.; Srirangam, J. K.; Barkoczy, J.; Williams, M. D.; Durkin, K. P. M.; Boyd, M. R.; Bai, R.; Hamel, E.; Schmidt, J. M.; Chapuis, J. C. Anti-Cancer Drug Des. 1995, 10, 529.