Synthesis and biological evaluation of new cross-conjugated dienone marine prostanoid analogues

Organic and Biomolecular Chemistry

Volumn 2, Issue 14, 2004, Pages 2028-2039

  Kuhn, Cyrille ^a   Roulland, Emmanuel ^a   Madelmont, Jean Claude ^a   Monneret, Claude ^a   Florent, Jean Claude ^a  

^a Laboratoire de Pharmacochimie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; COLUMN CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PROTEINS; SOLUBILITY; SOLUTIONS; SOLVENTS; SYNTHESIS (CHEMICAL);

CROSS-CONJUGATED DIENONES; CYTOTOXICITY; NUCLEAR PROTEINS; WITTIG REACTION;

AROMATIC COMPOUNDS;

ALDEHYDE; ALKENE; CYCLOPENTANE DERIVATIVE; PROSTAGLANDIN;

ANIMAL; ARTICLE; CELL DIVISION; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; MOUSE; STEREOISOMERISM; SYNTHESIS; TUMOR CELL LINE;

ALDEHYDES; ALKENES; ANIMALS; CELL DIVISION; CELL LINE, TUMOR; CYCLOPENTANES; DRUG EVALUATION, PRECLINICAL; MICE; PROSTAGLANDINS; STEREOISOMERISM;

EID: 3843086126     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b404016c     Document Type: Article

References (75)

1. (a) W. H. Gerwick, Chem. Rev., 1993, 93, 1807;
2. (b) A. D. Rodríguez, Tetrahedron, 1995, 51, 4571.
3. (a) M. Kobayashi, T. Yasuzawa, M. Yoshihara, H. Akutsu, Y. Kyogoku and I. Kitagawa, Tetrahedron Lett., 1982, 23, 5331;
4. (b) H. Kikuchi, Y. Tsukitani, K. Iguchi and Y. Yamada, Tetrahedron Lett., 1982, 23, 5171;
5. (c) K. Iguchi, S. Kaneta, K. Mori, Y. Yamada, A. Honda and Y. Mori, Tetrahedron Lett., 1985, 26, 5787.
6. (a) K. Iguchi, Y. Yamada, H. Kikuchi and Y. Tsukitami, Tetrahedron Lett., 1983, 24, 4433;
7. (b) K. Iguchi, S. Kaneta, K. Mori and Y. Yamada., Chem. Pharm. Bull., 1987, 35, 4375.
8. (a) B. J. Baker, R. K. Okuda, P. T. K. Yu and P. J. Scheuer, J. Am. Chem. Soc, 1985, 107, 2976;
9. (b) M. Suzuki, Y. Morita, A. Yanagisawa, B. J. Baker, P. J. Scheuer and R. Noyori, J. Org. Chem., 1988, 53, 286.
10. (a) M. Fukushima, Prostaglandins Leukorienes. Essent. Fatty Acids, 1992, 47, 1; M. Negishi, T. Koizumi and A. J. Ichikawa, Lipid Mediators, 1995, 12, 443.
11. (a) M. Fukushima, Prostaglandins Leukorienes. Essent. Fatty Acids, 1992, 47, 1; M. Negishi, T. Koizumi and A. J. Ichikawa, Lipid Mediators, 1995, 12, 443.
12. (a) S. Hashimoto, Y. Arai and N. Hamanaka, Tetrahedron Lett., 1985, 26, 2679; E. J. Corey and M. M. Mehrota, J. Am. Chem. Soc, 1984, 106, 3384;
13. (a) S. Hashimoto, Y. Arai and N. Hamanaka, Tetrahedron Lett., 1985, 26, 2679; E. J. Corey and M. M. Mehrota, J. Am. Chem. Soc, 1984, 106, 3384;
14. (b) J. Zhu, J.-Y. Yang, A. J. H. Klunder, Z.-Y. Liu and B. Zwanenburg, Tetrahedron, 1995, 51, 5847;
15. (c) M. Takemoto, A. Koshida, K. Miyazima, K. Suzuki and K. Achiwa, Chem. Pharm. Bull., 1991, 39, 1106;
16. (d) M. A. Ciufolini and S. Zhu, J. Org. Chem., 1998, 63, 1668;
17. (e) K. Mori and T. Takeuchi, Tetrahedron, 1988, 44, 333;
18. (f) M. Suzuki, Y. Morita, A. Yanagisawa, B. J. Baker, P. J. Scheuer and R. Noyori, J. Org. Chem., 1988, 53, 286;
19. (g) Z.-Y. Liu and X.-J. Chu, Tetrahedron, 1998, 54, 12561;
20. (h) M. A. Tius, M. Bust-Petersen and M. Yamashita, Tetrahedron Lett., 1998, 39, 4219;
21. (i) J. F. Bickley, V. Jadhav, S. M. Roberts, M. G. San toro, A. Steiner and P. W. Sutton, Synlett, 2003, 8, 1170.
22. T. Kato, M. Fukushima, S. Kurozumi and R. Noyori, Cancer Res., 1986, 46, 3538.
23. (a) For a recent review on new insights on biological activities and cellular targets, see: D. S. Straus and C. K. Glass, Med. Res. Rev., 2001, 21, 185; (b) S. M. Roberts, M. Santoro and E. Sickle, J. Chem. Soc., Perkin Trans. 1, 2002, 1735; (c) S. Narumiya, K. Ohno, M. Fukushima and M. Fujiwara, J. Pharmacol. Exp. Ther., 1987, 242, 306; mechanism of action: M. Suzuki, M. Mori, N. Terutake, R. Hirata, K. Furuta, T. Ishikawa and R. Noyori, J. Am. Chem. Soc., 1997, 119, 2376.
24. (a) For a recent review on new insights on biological activities and cellular targets, see: D. S. Straus and C. K. Glass, Med. Res. Rev., 2001, 21, 185; (b) S. M. Roberts, M. Santoro and E. Sickle, J. Chem. Soc., Perkin Trans. 1, 2002, 1735; (c) S. Narumiya, K. Ohno, M. Fukushima and M. Fujiwara, J. Pharmacol. Exp. Ther., 1987, 242, 306; mechanism of action: M. Suzuki, M. Mori, N. Terutake, R. Hirata, K. Furuta, T. Ishikawa and R. Noyori, J. Am. Chem. Soc., 1997, 119, 2376.
25. (a) For a recent review on new insights on biological activities and cellular targets, see: D. S. Straus and C. K. Glass, Med. Res. Rev., 2001, 21, 185; (b) S. M. Roberts, M. Santoro and E. Sickle, J. Chem. Soc., Perkin Trans. 1, 2002, 1735; (c) S. Narumiya, K. Ohno, M. Fukushima and M. Fujiwara, J. Pharmacol. Exp. Ther., 1987, 242, 306; mechanism of action: M. Suzuki, M. Mori, N. Terutake, R. Hirata, K. Furuta, T. Ishikawa and R. Noyori, J. Am. Chem. Soc., 1997, 119, 2376.
26. (a) For a recent review on new insights on biological activities and cellular targets, see: D. S. Straus and C. K. Glass, Med. Res. Rev., 2001, 21, 185; (b) S. M. Roberts, M. Santoro and E. Sickle, J. Chem. Soc., Perkin Trans. 1, 2002, 1735; (c) S. Narumiya, K. Ohno, M. Fukushima and M. Fujiwara, J. Pharmacol. Exp. Ther., 1987, 242, 306; mechanism of action: M. Suzuki, M. Mori, N. Terutake, R. Hirata, K. Furuta, T. Ishikawa and R. Noyori, J. Am. Chem. Soc., 1997, 119, 2376.
27. M. Fukushima, Eicosanoids, 1990, 3, 189; M. Fukushima, Prostaglandins, Leucotrienes Essent. Fatty Acids, 1992, 47, 1; H. Sasaki and M. Fukushima, Anti-Cancer Drugs, 1994, 5, 131.
28. M. Fukushima, Eicosanoids, 1990, 3, 189; M. Fukushima, Prostaglandins, Leucotrienes Essent. Fatty Acids, 1992, 47, 1; H. Sasaki and M. Fukushima, Anti-Cancer Drugs, 1994, 5, 131.
29. M. Fukushima, Eicosanoids, 1990, 3, 189; M. Fukushima, Prostaglandins, Leucotrienes Essent. Fatty Acids, 1992, 47, 1; H. Sasaki and M. Fukushima, Anti-Cancer Drugs, 1994, 5, 131.
30. P. Needleman, J. Turk, B. A. Kakschik, A. R. Morrison and J. B. Lefkowith, Ann. Rev. Biochem., 1986, 55, 69.
31. (a) M. G. Santoro, E. Garaci and C. Amici, Proc. Natl. Acad. Sci. USA, 1989, 86, 8407;
32. (b) M. G. Santoro, A. Banedetto, G. Garruba and E. Garaci, Science, 1980, 209, 1032;
33. (c) C. Rozera, A. Carattoli, A. De Marco, C. Amici and M. G. Santoro., J. Clin. Invest., 1996, 97, 1795;
34. (d) M. G. Santoro, Trends Microbiol., 1997, 5, 276.
35. (a) A. Ross, P. Kapachi, G. Natoli, T. Takahashi, Y. Chen and N. Karin, Nature, 2000, 403, 103;
36. (b) C. Ishika, R. Kanamura, T. Sato, T. Dei, Y. Konishi, M. A. Samura and A. Wakui, Cancer Res., 1988, 48, 2813;
37. (c) S. Takanishi, N. Odani, K. Tomokiyo, K. Furuta, M. Suzuki, A. Ichikawa and M. Negishi, Biochem. J., 1998, 335, 35;
38. (d) C. A. Vosseler, W. Erl and P. C. Weber, Biochem. Biophys. Res. Commun., 2003, 307, 322;
39. (e) S. Saito, S. Takahashi, N. Takagaki, T. Hirose and M. Sakai, Biochem. Biophys. Res. Commun., 2003, 311, 17.
40. N. J. Holbrook and M. Gorospe, Cancer Res., 1996, 56, 475; T. Ishikawa, K. Akimaru, M. Nakanishi, K. Tomokiyo, M. Furuta, Suzuki and R. Noyori, Biochem. J., 1998, 336, 569.
41. N. J. Holbrook and M. Gorospe, Cancer Res., 1996, 56, 475; T. Ishikawa, K. Akimaru, M. Nakanishi, K. Tomokiyo, M. Furuta, Suzuki and R. Noyori, Biochem. J., 1998, 336, 569.
42. D. K. Vanaja, M. E. Grossmann, E. Celis and C. Y. Young, Cancer Res., 2000, 60, 4714.
43. (a) C.-H. Hsiang and D. Straus, Oncogens, 2002, 21, 2212;
44. (b) M. Tanikawa, K. Yamada, K. Tominaga, H. Morizaki, Y. Kaneko, K. Ikeda, M. Suzuki, T. Kiho, K. Tomokiyo, K. Furuta, R. Noyori and M. Nakanishi, J. Btol. Chem., 1998, 273, 18522.
45. A. Rossi, G. Elia and M. G. Santoro, Proc. Nat. Acad. Sci., 1997, 94, 746.
46. (a) T. Satoh, K. Furuta, K. Tomokiyo, M. Suzuki and Y. Watanabe, Neurosci. Lett., 2000, 291, 167;
47. (b) K. Furuta, K. Tomokiyo, T. Satoh, Y. Watanabe and M. Suzuki, Chembiochem, 2000, 1, 283.
48. (a) C. Kuhn, G. Le Gouadec, A. L. Skaltsounis and J.-C. Florent, Tetrahedron Lett., 1995, 36, 3137;
49. (b) C. Kuhn and J.-C. Florent, Tetrahedron Lett., 1998, 39, 4247;
50. (c) E. Roulland, C. Monneret, J.-C. Florent, C. Bennejean, P. Renard and S. Léonce, J. Org. Chem., 2002, 67, 4399;
51. (d) C. Kuhn, L. Skaltsounis, C. Monneret and J.-C. Florent, Eur. J. Org. Chem., 2003, 14, 2585.
52. M. Suzuki, T. Kiho, K. Tomokiyo, K. Furuta, S. Fukushima, Y. Takeuchi, M. Nakanishi and R. Noyori, J. Med. Chem, 1998, 41, 3084.
53. S. Fukushima, S. Kishimoto, Y. Takeuchi and M. Fukushima, Adv. Drug Delivery Rev., 2000, 45, 65.
54. W. L. Wu and Y. L. Wu, J. Chem. Soc., Chem. Commun, 1993, 821.
55. K. Cruikshank and C. B. Reese, Synthesis, 1983, 3, 199.
56. A. W. M. Lee, V. S. Martin, S. Masamune, K. B. Sharpless and F. J. Walker, J. Am. Chem. Soc., 1982, 104, 3515.
57. For a closely-related example of acetal epimerisation during Wittig reaction, see: A. Gypser, M. Flasche and H.-D. Scharf, Liebigs Ann. Chem., 1994, 775.
58. (a) P. Allevi, P. Ciuffreda, G. Tarocco and H. Anastasia, Tetrahedron Lett., 1995, 36, 1347;
59. (b) P. Allevi, P. Ciuffreda, G. Tarocco and H. Anastasia, Tetrahedron: Asymmetry, 1995, 6, 2357.
60. S. Jarosz, S. Skoda, K. Szewczyk, C. Zbigniew and Z. Ciunik, Tetrahedron: Asymmetry, 2001, 12, 1895.
61. (a) E. A. Masu, K. A. Nelson, S. W. Densen and S. B. Hemperly, Org. Synth., 1989, 68, 92;
62. (b) A. Guerriero, M. D'Ambrosio and F. Pietra, Helv. Chim. Acta, 1990, 73, 2183.
63. K. Omura and D. Swern, Tetrahedron, 1978, 34, 1651.
64. E. J. Corey, A. Marfat, G. Giichi and F. Brion, J. Am. Chem. Soc., 1980, 102, 7984.
65. The para-fluoro substitution was chosen in order to lower the metabolism on the aromatic ring.
66. F. W. Lichtenthaler, P. Jarglis and K. Lorenz, Synthesis, 1988, 749.
67. Prepared from commercial dichloropropene: Van Romburgh, Recl. Trav. Chim. Pays-Bas, 1982, 234, 236; D. J. Burnell, H. B. Goodbrand, S. M. Kaiser and Z. Valenta, Can. J. Chem., 1987, 65, 154.
68. Prepared from commercial dichloropropene: Van Romburgh, Recl. Trav. Chim. Pays-Bas, 1982, 234, 236; D. J. Burnell, H. B. Goodbrand, S. M. Kaiser and Z. Valenta, Can. J. Chem., 1987, 65, 154.
69. For a recent synthesis of cross-conjugated dienones, see: (a) H. Tanaka, M. Kitade, M. Iwashima, K. Iguchi and T. Takahashi, Bioorg. Med. Chem. Lett., 2004, 14, 837; (b) M. Iqbal, Y. Li and P. Evans, Tetrahedron, 2004, 60, 2531; J. P. Eddolls, M. Iqbal, S. M. Roberts and M. G. Santoro, Tetrahedron, 2004, 60, 2539; (c) J. Dauvergne, A. M. Happe and S. M. Roberts, Tetrahedron, 2004, 60, 2551; H. Tanaka, T. Hasegawa, M. Iwashima, K. Iguchi and T. Takahashi, Org. Lett., 2004, in press.
70. For a recent synthesis of cross-conjugated dienones, see: (a) H. Tanaka, M. Kitade, M. Iwashima, K. Iguchi and T. Takahashi, Bioorg. Med. Chem. Lett., 2004, 14, 837; (b) M. Iqbal, Y. Li and P. Evans, Tetrahedron, 2004, 60, 2531; J. P. Eddolls, M. Iqbal, S. M. Roberts and M. G. Santoro, Tetrahedron, 2004, 60, 2539; (c) J. Dauvergne, A. M. Happe and S. M. Roberts, Tetrahedron, 2004, 60, 2551; H. Tanaka, T. Hasegawa, M. Iwashima, K. Iguchi and T. Takahashi, Org. Lett., 2004, in press.
71. For a recent synthesis of cross-conjugated dienones, see: (a) H. Tanaka, M. Kitade, M. Iwashima, K. Iguchi and T. Takahashi, Bioorg. Med. Chem. Lett., 2004, 14, 837; (b) M. Iqbal, Y. Li and P. Evans, Tetrahedron, 2004, 60, 2531; J. P. Eddolls, M. Iqbal, S. M. Roberts and M. G. Santoro, Tetrahedron, 2004, 60, 2539; (c) J. Dauvergne, A. M. Happe and S. M. Roberts, Tetrahedron, 2004, 60, 2551; H. Tanaka, T. Hasegawa, M. Iwashima, K. Iguchi and T. Takahashi, Org. Lett., 2004, in press.
72. For a recent synthesis of cross-conjugated dienones, see: (a) H. Tanaka, M. Kitade, M. Iwashima, K. Iguchi and T. Takahashi, Bioorg. Med. Chem. Lett., 2004, 14, 837; (b) M. Iqbal, Y. Li and P. Evans, Tetrahedron, 2004, 60, 2531; J. P. Eddolls, M. Iqbal, S. M. Roberts and M. G. Santoro, Tetrahedron, 2004, 60, 2539; (c) J. Dauvergne, A. M. Happe and S. M. Roberts, Tetrahedron, 2004, 60, 2551; H. Tanaka, T. Hasegawa, M. Iwashima, K. Iguchi and T. Takahashi, Org. Lett., 2004, in press.
73. For a recent synthesis of cross-conjugated dienones, see: (a) H. Tanaka, M. Kitade, M. Iwashima, K. Iguchi and T. Takahashi, Bioorg. Med. Chem. Lett., 2004, 14, 837; (b) M. Iqbal, Y. Li and P. Evans, Tetrahedron, 2004, 60, 2531; J. P. Eddolls, M. Iqbal, S. M. Roberts and M. G. Santoro, Tetrahedron, 2004, 60, 2539; (c) J. Dauvergne, A. M. Happe and S. M. Roberts, Tetrahedron, 2004, 60, 2551; H. Tanaka, T. Hasegawa, M. Iwashima, K. Iguchi and T. Takahashi, Org. Lett., 2004, in press.
74. E. Hungerbühler and D. Seebach, Helv. Chim. Acta, 1981, 70, 687.
75. X. P. Gu, N. Nishida, I. Takeda and M. Okahara, J. Org. Chem., 1987, 52, 3192.