Towards the syntheses of N-H and N-alkylated derivatives of meridianins

Journal of Heterocyclic Chemistry

Volumn 44, Issue 4, 2007, Pages 793-801

  Simon, Gaëlle ^d   Couthon Gourves, Hélène ^d   Haelters, Jean Pierre ^d   Corbel, Bernard ^a   Kervarec, Nelly ^d   Michaud, François ^b   Meijer, Laurent ^c  

^a Centre National de la Recherche Scientifique   (France)

^b UFR SCIENCES ET TECHNIQUES   (France)

^c STATION BIOLOGIQUE   (France)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; INDOLE ALKALOID; MERIDIANIN; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MARINE SPECIES; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

EID: 36749074458     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570440407     Document Type: Article

References (65)

1. (a) Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1-49.
2. (b) Newman, D. J.; Cragg, G. M.; Snader, K. M. J. Nat. Prod. 2003, 66, 1022-1037.
3. (c) Mayer, A. M. S.; Hamann, M. T. Mar. Biotechnol. 2004, 6, 37-52.
4. (d) Blunt, J. W.; Cop, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prop. Rep. 2005, 22, 15-61.
5. (a) Hibino, S.; Choshi, T. Nat. Prod. Rep. 2002, 19, 148-180.
6. (b) Pindur, U.; Lemster, T. Curr. Med. Chem. 2001, 8, 1681-1698.
7. (a) Sakemi, S.; Sun, H. H. J. Org. Chem. 1991, 56, 4304-4307.
8. (b) Kawasaki, Y.; Yamashita, M.; Otha, S. J. Chem. Soc., Chem. Commun. 1994, 2085-2086.
9. (c) Kawasaki, Y.; Yamashita, M.; Otha, S. Chem. Pharm. Bull. 1996, 44, 1831-1839.
10. (d) Bartik, K.; Braekman, J. C.; Daloze, D.; Stoller, C.; Huysecom, J.; Vandevyver, G.; Ottinger, R. Can. J. Chem. 1987, 65, 2118-2121.
11. (e) Braekman, J. C.; Daloze, D.; Stoller, C. Bull. Soc. Chim. Belg. 1987, 96, 809-812.
12. (f) Tsujii, S.; Rinehart, K. L.; Gunasekera, S. P.; Kashman, Y.; Cross, S. S.; Lui, M. S.; Pomponi, S. A.; Diaz, M. C. J. Org. Chem. 1988, 53, 5446-5453.
13. (g) Morris, S. A.; Andersen, R. J. Tetrahedron 1990, 46, 715-720.
14. (h) Kawasaki, Y.; Katsuma, H.; Nakayama, Y.; Yamashita, M.; Otha, S. Heterocycles 1998, 48, 1887-1901.
15. Vervoort, H. C.; Richards-Gross, S. E.; Fenical, W.; Lee, A. Y.; Clardy, J. J. Org. Chem. 1997, 62, 1486-1490.
16. (a) Takahashi, S.; Matsunaga, T.; Hasegawa, C.; Saito, H.; Fujita, D.; Kiuchi, F.; Tsuda, Y. Chem. Pharm. Bull. 1998, 46, 1527-1529.
17. (b) N'Diaye, Y.; Guella, G.; Chiasera, G.; Mancini, Y.; Pietra, F. Tetrahedron Lett. 1994, 35, 4827-4830.
18. (c) Guella, G.; Mancini, Y.; N'Diaye, Y.; Pietra, F. Helv. Chim. Acta 1999, 77, 1203-1221.
19. Bergmann, T.; Schories, D.; Steffan, B. Tetrahedron 1997, 53, 2055-2060.
20. Kohmoto, S.; Kashman, Y.; McConnell, O. J.; Rinehart, K. L.; Wright, A.; Koehn, F. J. Org. Chem. 1988, 53, 3116-3118.
21. Jakse, R.; Svete, J.; Stanovnik, B.; Golobic, A. Tetrahedron 2004, 60, 4601-4608.
22. (a) Franco, L. H. ; De Kier Joffe, E. B. ; Puricelly, L. ; Tatian, M. ; Seldes, A. M. ; Palermo, J. A. J . Nat. Prod. 1998, 61, 1130-1132.
23. (b) Perry, N. B.; Ettouati, L.; Litaudon, M.; Blunt, J. W.; Munro, M. H. G.; Parkin, S.; Hope H. Tetrahedron 1994, 50, 3987-3992.
24. (c) Trimurtulu, G.; Faulkner, D. J.; Perry, N. B.; Ettouati, L.; Litaudon, M.; Blunt, J. W.; Munro, M. H. G.; Jameson, G. B. Tetrahedron 1994, 50, 3993-4000.
25. Gompel, M.; Leost, M.; De Kier Joffe, E. B.; Puricelli, L.; Hernandez Franco, L.; Palermo, J.; Meijer, L. Bioorg. Med. Chem. Lett. 2004, 14, 1703-1707.
26. Jiang, B.; Yang, C.-G. Heterocycles 2000, 53, 1489-1498.
27. Fresneda, P. M.; Molina, P.; Bleda, J. A. Tetrahedron 2001, 57, 2355-2363.
28. (a) Abdulla, R. F.; Brinkmeyer, R. S. Tetrahedron 1979, 35, 1675-1735.
29. (b) Stanovnik, B.; Steve, J. Chem. Rev. 2004, 104, 2433-2480.
30. Bredereck, H.; Effenberger, F.; Butsch, H.; Rehn H. Chem. Ber. 1965, 98, 1081-1086.
31. Karpov A. S., Merkul E., Rominger F., Müller T. J. J. Angew. Chem. Int. Ed .2005, 44, 6951-6956.
32. Batcho, A. D.; Leimgruber, W. Org. Synth., coll. Vol. VII 1990, 34-41.
33. Bartoli, G.; Palmieri, G.; Bosco, M.; Dalpozzo, R. Tetrahedron Lett. 1989, 2757-2761.
34. Illi, V. O. Synthesis 1979, 387-388.
35. (a) Ketcha, D. M.; Gribble, G. W. J. Org. Chem. 1985, 50, 5451-5457.
36. (b) Ketcha, D. M.; Lieurance, B. A.; Homan, D. F. J. J. Org. Chem. 1989, 54, 4350-4356.
37. (a) Brechbuehler, H.; Buchi, H.; Hatz, E.; Schreiber, J.; Eschenmoser, A. Helv. Chim. Acta 1965, 48, 1746-1771.
38. (b) Vorbruggen, H. Angew. Chem. Internat. Ed. 1963, 2, 211-212 .
39. (c) Zemlicka, J. Coll. Czech. Chem. Commun. 1963, 28, 1060-1062.
40. (d) Stanovnik, B.; Tisler, M.; Hribar, A.; Barlin, G. B.; Brown, D. J. Aust. J. Chem. 1981, 34, 1729-1738.
41. (a) Middelton, R. W.; Monney, H.; Parrick, J. Synthesis 1984, 740-743.
42. (b) Philips, K. D.; Horwitz, J. P. J. Org. Chem. 1975, 40, 1856-1858.
43. (a) Bejan, E.; Aït Haddou, H.; Daran, J. C.; Balavoine, G. G. A. Synthesis 1996, 1012-1018;
44. (b) Bredereck, H.; Effenberger, F.; Botsch, H.; Rehn, H. Chem. Ber. 1965, 98, 1081-1086.
45. Gray, N.; Detivaud, L.; Doerig, C.; Meijer, L. Current Med. Chem. 1999, 6, 859-875.
46. Pindur, U.; Lemster, T. Current Med. Chem. 2001, 8, 1681-1698.
47. (a) Carle, J. S.; Christophersen, C. J. Am. Chem. Soc. 1979, 101, 4012-4013.
48. (b) Carle, J. S.; Christophersen, C. J. Org. Chem. 1980, 45, 1586-1589.
49. Bacher, G.; Nickel, B.; Emig, P.; Vanhoefer, U.; Seeber, S.; Shandra, A.; Klenner, T.; Beckers, T. Cancer Res. 2001, 61, 392-399.
50. (a) Sundberg, R. J. "The chemistry of indoles", Acad. Press, New York, 1970.
51. (b) Sundberg, R. J. "Comprehensive Heterocyclic Chemistry", Katrisky, A. R.; Rees, C. W.; Bird, C. W.; Cheeseman, G. W. H. Eds, Pergamon, Oxford, 1984, vol. 4, 313-376.
52. (c) Sundberg, R. J. "indoles", Acad. Press, San Diego CA, 1996.
53. Ottoni, O.; Neder, A. de V. F.; Dias, A. K. B.; Cruz, R. P. A.; Aquino, L. B. Org. Lett. 2001, 3, 1005-1007.
54. Ottoni, O.; Cruz, R.; Alves, R. Tetrahedron 1998, 54, 13915-13928.
55. Berger, J.; Flippin, L. A.; Greenhouse, R.; Jaime-Figueroa, S.; Liu, Y.; Miller, A. K.; Putman, D. G.; Weinhardt, K. K.; Zhao, S.-H.; US 5 958 934 (1999) and US 5 863 924 (1999).
56. (a) Bredereck, H.; Simchen, G. Angew Chem. Int. Ed. 1963, 2, 738.
57. (b) Bredereck, H.; Simchen, G.; Wahl, R. Chem. Ber. 1968, 101, 4048-4056.
58. (a) Knockaert, M.; Grenngard, P.; Meijer, L. Trends Pharmacol. Sci. 2002, 23, 417-425.
59. (b) Hardcastle, I. R.; Golding, B. T.; Griffin, R. J. Annu. Rev. Pharmacol. Toxicol. 2002, 42, 325-348.
60. Martinez, A.; Castro, A.; Dorronsoro, I.; Alonso, M. Medic. Res. Rev. 2002, 22, 373-384.
61. (a) Leclerc, S.; Garnier, M.; Hoesser, R.; Marko, D.; Bibb, J. A.; Snyder, G. L.; Greengard, P.; Biernat, J.; Mandelkow, E.-M.; Eisenbrand, G.; Meijer, L. J. Biol. Chem. 2001, 276, 251-260.
62. (b) Fabbro, D.; Ruetz, S.; Buchdunger, E.; Cowan-Jacob, S. W.; Fendrich, G.; Liebetanz, J.; Mestan, J.; O'Reilly, T.; Traxler, P.; Chaudhuri, B.; Fretz, H.; Zimmermann, J.; Meyer, T.; Caravatti, G.; Furet, P.; Manley, P. W. Pharmacology & Therapeutics 2002, 93, 79-98 (and ref. therein).
63. (a) Furet, P. Curr. Med. Chem. Anticancer Agents 2003, 3, 15-23.
64. (b) Fischer, P. M.; Endicott, J.; Meijer, L. Progr. Cell Cycle Res. 2003, 5, 235-248.
65. Jiang, B.; Yang, C.-G.; Xiong, W.-N.; Wang, J. Bioorg. Med. Chem. 2001, 9, 1149-1154.