Progress in studies of novel marine bis(indole) alkaloids

Current Organic Chemistry

Volumn 8, Issue 17, 2004, Pages 1691-1720

  Yang, Cai Guang ^a   Huang, Hao ^a   Jiang, Biao ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; MARINE BIOLOGY; METABOLITES; POLYCYCLIC AROMATIC HYDROCARBONS; SYNTHESIS (CHEMICAL);

BIS-INDOLES; DEEPWATER; HETEROCYCLIC MOIETIES; IMIDAZOL; INDOLE ALKALOIDS; INDOLE RINGS; MARINE ORGANISMS; MARINE SPONGE; NATURAL PRODUCTS; TOTAL SYNTHESIS;

ALKALOIDS;

4,5 DIHYDRO 6' DEOXYBROMOTOPSENTIN; ALKALOID DERIVATIVE; BROMODEOXYTOPSENTIN; BROMOTOPSENTIN; DEOXYTOPSENTIN; DRAGMACIDIN DERIVATIVE; HAMACANTHIN DERIVATIVE; HOE 33342; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; ISOBROMODEOXYTOPSENTIN; ISOBROMOTOPSENTIN; MANOALIDE; NATURAL PRODUCT; NORTOPSENTIN A; NORTOPSENTIN B; NORTOPSENTIN C; NORTOPSENTIN D; NORTOPSENTIN DERIVATIVE; NORTOPSENTIN E; RACHELMYCIN; RHOPALADIN A; RHOPALADIN B; RHOPALADIN C; RHOPALADIN D; RHOPALADIN DERIVATIVE; TOPSENTIN; TOPSENTIN C; TOPSENTIN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANALYTIC METHOD; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG DNA BINDING; DRUG ISOLATION; DRUG MECHANISM; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IC 50; IN VITRO STUDY; MARINE ENVIRONMENT; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; REVIEW; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 5744247694     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043369656     Document Type: Review

References (92)

1. Krebs, H.G. in Progress in the chemistry of organic natural products. Edited by Herz, W.; Grisebach, H.; Kirby, G.W.; Tamm, C. Springer-Verlag Wien, New York. 1986, Vol. 49, P. 151.
2. Deng, S.Z. Tianran Chanwu Yanjiu Yu Kaifa, 1997, 9 156.
3. Faulkner, D.J. Nat. Prod Rep., 2001, 18, 1-49 and references cited therein.
4. Flam, F. Science, 1994, 266, 1324.
5. Bartik, K.; Braekman, J.-C.; Daloze, D.; Stoller, C.; Huysecom, J.; Vandevyver, G.; Ottinger, R. Can. J. Chem., 1987 65, 2118.
6. Norton, R.S.; Wells, R.J. J. Am. Chem. Soc., 1982 104, 3628.
7. Moquin, C.; Guyot, M. Tetrahedron Lett., 1984, 25, 5047.
8. Christophersen, C. in The alkaloids. Vol. XXIV. Edited by Brossi, A. Academic Press, New York. 1985.
9. Christophersen, C. in Marine natural products. Vol. V. Edited by Scheuer, P.J. Academic Press, New York. 1983.
10. Tsujii, S.; Rinehart, K.L. J. Org. Chem., 1988, 53, 5446.
11. Morris, S.A.; Andersen, R.J. Can. J. Chem., 1989, 67, 677.
12. Morris, S.A.; Andersen, R.J. Tetrahedron, 1990, 46, 715.
13. Murray, L.M.; Lim, T.K.; Hooper, J.N.A.; Capon, R.J. Aust. J. Chem., 1995, 48, 2053.
14. Shin, J.; Seo, Y.; Cho, K.W.; Rho, J.-R.; Sim, C.J. J. Nat. Prod., 1999, 62, 647.
15. Burres, N.S.; Barber, D.A.; Gunasekera, S.P.; Shen, L.L.; Clement, J.J. Biochem. Pharmacol., 1991, 42, 745.
16. Rinehart, K.L.; Tachibana, K. J. Nat. Prod., 1995 58, 344.
17. For a review, see: Wylie, B.L.; Ernst, N.B.; Grace, K.J.S.; Jacobs, R.S. Prog. Surg., 1997, 24, 146.
18. McConnell, O.J.; Saucy, G.; Jacobs, R. U.S. Patent 5290777; Chem. Abstr., 1994, 120, 236178.
19. Casapullo, A.; Bifulco, G.; Bruno, I.; Riccio, R. J. Nat. Prod., 2000, 63, 447.
20. Phife, D.W.; Ramos, R.A.; Feng, M.; King, I.; Gunasekera, S.P.; Wright, A.; Patel, M.; Pachter, J.A.; Coval, S.J. Bioorg. Med. Chem. Lett., 1996, 6, 2103.
21. Gunasekera, SP.; Cross, S.S. Eur. Patent 304157; Chem. Abstr., 1990, 111, 160196.
22. Gunasekera, S.P.; Cross, S.S.; Kashman, Y.; Liu, M.S. Eur. Patent 272810; Chem. Abstr., 1989, 109, 129417.
23. Gunasekera, S.P.; Cross, S.S.; Kashman, Y.; Liu, M.S.; Rinehart, K.L.; Tsujii, S. U.S. Patent 4866084; Chem. Abstr., 1990, 112, 185775.
24. McConnell, O.J.; Saucy, G.; Jacobs, R.; Gunasekera, S.P. U.S. Patent 5464835; Chem. Abstr., 1996, 124, 76517.
25. Jacobs, R.S.; Pomponi, S.; Gunasekera, S.P.; Wright, A. WO Patent 9818466; Chem. Abstr., 1999, 129, 587.
26. Wright, A.; Pomponi, S.A.; Jacobs, R.S. WO Patent 9942092; Chem. Abstr., 2000, 131, 175081.
27. Braekman, J.C.; Daloze, D.; Stoller, C. Bull. Soc. Chim. Belg., 1987, 96, 809-812.
28. Koga, M.; Anselme, J.P. J. Chem. Soc. Chem. Comm., 1973, 52.
29. Koga, M.; Stamegna, A.P.; Burke, D.J.; Anselme, J.P. J. Chem. Educ., 1977, 54, 111.
30. Kalinin, V.N. Synthesis, 1992, 413-432.
31. Martin, A.R.; Yang, Y. Acta Chem. Scand., 1993, 47, 221.
32. Achab, S. Tetrahedon Lett., 1996, 37, 5503.
33. Ohta, S.; Yamamoto, T.; Kawasaki, I.; Yamashita, M.; Katsuma, H.; Nasako, R.; Kobayashi, K.; Ogawa, K. Chem. Pharm. Bull., 1992, 40, 2681.
34. Ohta, S.; Yamamoto, T.; Kawasaki, I.; Yamashita, M.; Nagashima, Y.; Yoshikawa, T. Chem. Pharm. Bull., 1994, 42 821.
35. Kawasaki, I.; Taguchi, N.; Yamamoto, T.; Yamashita, M.; Ohta, S. Tetrahedron Lett., 1995, 36, 8251.
36. Kawasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc. Chem. Comm., 1994, 2085.
37. Kawasaki, I.; Taguchi, N.; Yoneda, Y.; Yamashita, M.; Ohta, S. Herterocycles, 1996, 43, 1375.
38. Kawasaki, I.; Yamashita, M.; Ohta, S. Chem. Pharm. Bull. 1996, 44, 1831.
39. Kawasaki, I.; Taguchi, N.; Yamashita, M.; Ohta, S. Chem. Pharm. Bull., 1997, 45, 1393.
40. Kawasaki, I.; Katsuma, H.; Nakayama, Y.; Yamashita, M.; Ohta, S. Herterocycles, 1998, 48, 1887.
41. Miyake, F.Y.; Yakushijin, K.; Horne, D.A. Org. Lett., 2000, 2, 2121.
42. Sakemi, S.; Sun, H.H. J. Org. Chem., 1991, 56 4304.
43. Sun, H.H.; Sakemi, S.; Gunasekera, S.; Kashman, Y.; Lui, M.; Burres, N.; McCarthy, P. U.S. Patent 4970226; Chem. Abstr., 1991 115, 35701z.
44. Knubel, G.; Larsen, L.K., Moore, R.E.; Levine, I.A.; Patterson, G.M.L. J. Antibiot., 1990, 43, 1236.
45. Mancini, I.; Guella, G.; Debitus, C.; Waikedre, J.; Pietra, F. Helv. Chim. Acta, 1996, 79, 2075.
46. Longley, R.E.; Isbrucker, R.A.; Wright, A.E. U.S. Patent 6087363; Chem. Abstr. 2000, 133, 99589.
47. Kumashiro, K.; Masukawa, T.; Kimura, T. Jpn. Kokai Tokkyo Koho JP 01238661 A2, 22 Sep 1989, Heisei.
48. Yoshikawa, Y.; Ouchi, Y.; Saito, H.; Hatayama, K. Jpn. Kokai Tokkyo Koho JP 02188579 A2, 24 Jul 1990, Heisei.
49. Little, T.L.; Webber, S.E. J. Org. Chem., 1994, 59, 7299.
50. Brederack, H.; Theilig, G. Chem. Ber., 1953, 86, 88.
51. Van Leusen, A.M.; Wildeman, J.; Oldenziel, O.H. J. Org. Chem., 1977, 42, 1153.
52. Moody, C.J.; Roffey, J.R.A. ARKIVOC 2000, 1, Part 3 393; Chem. Abstr. 2001, 134, 71748.
53. Fresneda, P.; Molina, P.; Sanz, M.A. Synlett, 2001 218.
54. Sato, H.; Tsuda, M.; Watanabe, K.; Kobayashi, J. Tetrahedron, 1998, 54, 8687.
55. Molina, P.; Fresneda, P.M.; Sanz, M.A. J. Org. Chem., 1999, 64, 2540 and references cited therein.
56. Fresneda, P.M.; Molina, P.; Sanz, M.A. Synlett, 2000 1190.
57. Gunasekera, S.P.; McCarthy, P.J.; Kelly-Borges, M. J. Nat. Prod., 1994, 57, 1437.
58. "CRC Handbook of Microbiology," Edited by Laskin, A.I.; Lechevalier, H.A. CRC Press, Boca Raton, FL, 1984, Vol. 5, pp. 623-626.
59. Jiang, B.; Yang, C.-G.; Wang, J. J. Org. Chem., 2001 66, 4865.
60. Jiang, B.; Yang, C.-G.; Wang, J. J. Org. Chem., 2002 67, 1396.
61. Yang, C.-G.; Wang, J.; Tang, X.-X; Jiang, B. Tetrahedron: Asymmetry, 2002, 43, 1063.
62. Miyake, F.Y.; Yakushijin, K.; Horne, D.A. Org. Leet., 2002, in press.
63. Kohmoto, S.; Kashman, Y.; McConnell, O.J.; Rinehart, K.L., Wright, A.; Koehn, F. J. Org. Chem., 1988, 53, 3116.
64. Fahy, E.; Potts, B.C.M.; Faulkner, D.J. J. Nat. Prod., 1991, 54, 564.
65. Wright, A.E.; Pomponi, S.A.; Cross, S.S.; McCarthy, P. J. Org. Chem., 1992, 57, 4772.
66. Keifer, P.A.; Schwartz, R.E.; Koker, M.E.S.; Hughes, R.G.; Rittschof, D.; Rinehart, K.L. J. Org. Chem., 1991, 56, 2965 and references contained therein.
67. Cimino, G.; De Ross, S.; Self, R.; Sodano, G. Tetrahedron Lett., 1983, 24, 3029.
68. Capon, R.J.; Rooney, F.; Murray, L.M.; Collins, E.; Sim, A.T.R.; Rostas, J.A.P.; Butler, M.S.; Carroll, A.R. J. Nat. Prod., 1998, 61, 660.
69. Cutignano, A.; Bifulco, G.; Bruno, I.; Casapullo, A.; Gomez-Paloma, L.; Riccio, R. Tetrahedron, 2000, 56, 3743.
70. Jiang, B.; Smallheer, J.M.; Amaral-Ly, C.; Wuonola, M.A. J. Org. Chem., 1994, 59, 6823.
71. Whitlock, C.R.; Cava, M.P. Tetrahedron Lett., 1994 35, 371.
72. Miyake, F.Y.; Yakushijin, K.; Horne, D.A. Org. Lett., 2000, 2, 3185.
73. Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto, M. Org. Lett., 2000, 2, 3027.
74. Clark, B.P.; Harris, J.R. Synth. Commun., 1997, 27, 4223.
75. Johannsen, M. J. Chem. Soc. Chem. Commun., 1999, 2233.
76. Jiang, B.; Yang, C.-G.; Gu, X.-H. Tetrahedron Lett., 2001, 42, 2545.
77. Jiang, B.; Gu, X.-H. Heterocycles, 2000, 53 1559.
78. Yang, C.-G.; Wang, J.; Jiang, B. Tetrahedron Lett., 2002, 43, 1063.
79. Wipf, P. Chem. Rev., 1995, 95, 2115.
80. Rubinstein, L.V.; Shoemaker, R.H.; Paull, K.D.; Simon, R.M.; Tosini, S.; Skehan, P.; Scudiero, D.A.; Monks, A.; Boyd, M.R. J. Natl. Cancer Inst., 1990, 82, 1113.
81. Skehan, P.; Storeng, R.; Scudiero, D.A.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J.T.; Bokesch, H.; Kenney, S.; Boyd, M.R. J. Natl. Cancer Inst., 1990, 82, 1107.
82. Grever, M.R.; Schepatz, S.A.; Chabner, B.A. Seminars in Oncology, 1992, 19, 622.
83. Alley, M.C.; Scudiero, D.A.; Monks, A.; Hursey, M.L.; Czerwinski, M.J.; Fine, D.L. Cancer Res., 1988, 48, 589.
84. Mosmman, T. J. Immunol Meth., 1983, 65, 55.
85. Qing, C.; Zhang, J.-S.; Ding, J. Acta Pharmacol Sin., 1999, 20, 297.
86. Gu, X.-H.; Wan, X.-Z.; Jiang, B. Bioorg. Med. Chem. Lett. 1999, 9, 569.
87. Jiang, B.; Gu, X.-H. Bioorg. Med. Chem., 2000, 8, 363.
88. Jiang, B.; Yang, C.-G. Heterocycles, 2000, 53 1489.
89. Jiang, B.; Yang, C.-G.; Xiong, W.-N.; Wang, J. Bioorg & Med Chem., 2001, 9, 1149.
90. Jiang, B.; Xiong, W.-N.; Yang, C.-G. Bioorg & Med Chem. Lett., 2001, 11, 475.
91. Xiong, W.-N.; Yang, C.-G.; Jiang, B. Bioorg & Med Chem. 2001, 9, 1773.
92. Jiang B.; Xiong, W.-N.; Yang, C.-G.; Jiang, H.-L.; Cheng, F.; Chen, K.-X. Bioorg & Med Chem., 2002, 10, 2775.