Solid-phase synthesis and biological activity of a combinatorial cross-conjugated dienone library

Chemistry - A European Journal

Volumn 12, Issue 5, 2006, Pages 1368-1376

  Kitade, Makoto ^a,c   Tanaka, Hiroshi ^a   Oe, Sho ^a   Iwashima, Makoto ^b,d   Iguchi, Kazuo ^b   Takahashi, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^c TAIHO PHARMACEUTICAL CO LTD   (Japan)

^d UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Alkylation; Chemical biology; Clavulone; Combinatorial chemistry prostanoids; Solid phase synthesis

Indexed keywords

ACETYLENE; ALDEHYDES; ALKYLATION; BIODIVERSITY; CONDENSATION; HALIDE MINERALS; SYNTHESIS (CHEMICAL);

CHEMICAL BIOLOGY; CLAVULONE; COMBINATORIAL CHEMISTRY PROSTANOIDS; DIENONE LIBRARY; SOLID PHASE SYNTHESIS;

KETONES;

ANTINEOPLASTIC ANTIBIOTIC; CLAVULONES; DOXORUBICIN; PROSTAGLANDIN A;

ARTICLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG EFFECT; HUMAN; SYNTHESIS; TUMOR CELL LINE;

ANTIBIOTICS, ANTINEOPLASTIC; CELL LINE, TUMOR; CELL PROLIFERATION; COMBINATORIAL CHEMISTRY TECHNIQUES; DOXORUBICIN; HUMANS; MOLECULAR STRUCTURE; PROSTAGLANDINS A;

EID: 32044473712     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500793     Document Type: Article

References (59)

1. a) D. A. Campbell, A. K. Szardenings, Curr. Opin. Chem. Biol. 2003, 7, 296-303;
2. b) L. F. Tietze, H. P. Bell, S. Chandrasekhar, Angew. Chem. 2003, 115, 4128-4160;
3. Angew. Chem. Int. Ed. 2003, 42, 3996-4028.
4. a) J.-Y. Ortholand, A. Ganesan, Curr. Opin. Chem. Biol. 2004, 8, 271-280;
5. b) A. M. Boldi, Curr. Opin. Chem. Biol. 2004, 8, 281-286;
6. A Ganesan, Curr. Opin. Biotechnol. 2004, 15, 584-590.
7. a) D. Brohm, S. Metzger, A. Bhargava, O. Muller, F. Lieb, H. Waldmann, Angew. Chem. 2002, 114, 319-323;
8. Angew. Chem. Int. Ed. 2002, 41, 307-311;
9. b) M. A. Koch, R. Breinbauer, H. Waldmann, Biol. Chem. 2003, 384, 1265-1272.
10. For our results of the synthesis of combinatorial libraries based on the structure of natural products, see: a) T. Doi, I. Hijikuro, T. Takahashi, J. Am. Chem. Soc. 1999, 121, 6749-6750;
11. b) A. Matsuda, T. Doi, H. Tanaka, T. Takahashi, Synlett 2001, 1101-1104;
12. I. Hijikuro, T. Doi, T. Takahashi, J. Am. Chem. Soc. 2001, 123, 3716-3722;
13. H. Ohno, K. Kawamura, A. Otake, H. Nagase, H. Tanaka, T. Takahashi, Synlett 2002, 93-96;
14. e) H. Tanaka, T. Zenkoh, H. Setoi, T. Takahashi, Synlett 2002, 1427-1430;
15. f) T. Takahashi, H. Nagamiya, T. Doi, P. G. Griffiths, M. Andrew, A. M. Bray, J. Comb. Chem. 2003, 5, 414-428;
16. g) H. Tanaka, H. Ohno, K. Kawamura, A. Ohtake, H. Nagase, T. Takahashi, Org. Lett. 2003, 5, 1159-1162;
17. h) H. Tanaka, M. Moriwaki, T. Takahashi, Org. Lett. 2003, 5, 3807-3809;
18. T. Takahashi, S. Kusaka, T. Doi, T. Sunazuka, S. Omura, Angew. Chem. 2003, 115, 5388-5392;
19. Angew. Chem. Int. Ed. 2003, 42, 5230-5234.
20. a) M. Fukushima, Prostaglandins Leukotrienes Essent. Fatty Acids 1992, 47, 1-12.
21. 1 and related compounds, see: a) R. Noyori, M. Suzuki, Science 1993, 259, 44-45;
22. b) M. Suzuki, M. Mori, T. Niwa, R. Hirata, K. Furuta, T. Ishikawa, R. Noyori, J. Am. Chem. Soc. 1997, 119, 2376-2385;
23. A. Rossi, G. Elia, G. M. Santoro, Proc. Natl. Acad. Sci. USA 1997, 94, 746-750;
24. M. Suzuki, T. Kawagishi, A. Yanagisawa, T. Suzuki, N. Okamura, R. Noyori, Bull. Chem. Soc. Jpn. 1988, 61, 1299-1312;
25. e) M. Negishi, H. Katoh, Prostaglandins Other Lipid Mediat. 2002, 68, 611-617.
26. 2 and related compounds, see: a) B. M. Forman, P. Tontonoz, J. Chen, R. P. Brun, B. M. Spiegelman, R. M. Evans, Cell 1995, 83, 803-812;
27. b) M. Ricote, A. C. Li, T. M. Willson, C. J. Kelly, C. K. Glass, Nature 1998, 391, 79-82;
28. T. V. Petrova, K. T. Akama, L. J. Van Edlik, Proc. Natl. Acad. Sci. USA 1999, 96, 4668-4673;
29. A. Rossi, P. Kapahi, G. Natoli, T. Takahashi, Y. Chen, M. Karin, G. M. Santro, Nature 2000, 403, 103-108;
30. e) D. S. Straus, G. Pascual, M. Li, J. S. Welch, M. Ricote, C.-H. Hsiang, L. L. Sengchanthalangsy, G. Ghosh. Proc. Natl. Acad. Sci. USA 2000, 97, 4844-4849;
31. f) M. Kondo, T. Shibata, T. Kumagai, T. Osawa, N. Shibata, M. Kobayashi, S. Sasaki, M. Iwata, N. Noguchi, K. Uchida, Proc. Natl. Acad. Sci. USA 2002, 99, 7367-7372;
32. g) T. Shibata, T. Yamada, M. Kondo, N. Tanahashi, K. Tanaka, H. Nakamura, H. Masutani, J. Yodoi, K. Uchida, Biochemistry 2003, 42, 13960-13968;
33. h) J. L. Oliva, D. Pérez-Sala, A. Castrillo, N. Martínez, F. J. Cañada, L. Boscá, J. M. P. Rojas, Proc. Natl. Acad. Sci. USA 2003, 100, 4772.
34. a) H. Kikuchi, Y. Tsukitani, K. Iguchi, Y. Yamada. Tetrahedron Lett. 1982, 23, 5171-5174;
35. b) M. Kobayashi, T. Yasuzawa, M. Yoshihara, H. Akutsu, Y. Kyogoku, I. Kitagawa, Tetrahedron Lett. 1982, 23, 5331-5334;
36. K. Iguchi, Y. Yamada, H. Kikuchi, Y. Tsukitani, Tetrahedron Lett. 1983, 24, 4433-4434;
37. K. Iguchi, S. Kaneta, K. Mori, Y. Yamada, A. Honda, Y. Mori, Tetrahedron Lett. 1985, 26, 5787-5790;
38. e) M. Iwashima, K. Okamoto, F. Konno, K. Iguchi, J. Nat. Prod. 1999, 62, 352-354;
39. f) T. Rezanka, V. M. Dembitsky, Eur. J. Org. Chem. 2003, 309-316.
40. a) E. J. Corey, M. Mehrotra, J. Am. Chem. Soc. 1984, 106, 3384;
41. b) H. Nagaoka, T. Miyakoshi, Y. Yamada, Tetrahedron Lett. 1984, 25, 3621-3624;
42. S. Hashimoto, Y. Arai, N. Hamanaka, Tetrahedron Lett. 1985, 26, 2679-2682;
43. M. Shibasaki, Y. Ogawa, Tetrahedron Lett. 1985, 26, 3841-3844.
44. a) M. A. Ciufolini, S. Zu, J. Org. Chem. 1998, 63, 1668-1675;
45. b) A. J. H. Klunder, B. Zwanenburg, Tetrahedron Lett. 1991, 32, 3131-3132;
46. K. Takeda, A. Nakajima, E. Yoshii, Synlett 1997, 255-256;
47. J. Zhu, J.-Y. Yang, A. J. H. Klunder, Z.-Y. Liu, B. Zwanenburg, Tetrahedron 1995, 57, 5847-5870;
48. e) M. A. Tius, H. Hu, J. K. Kawakami, J. Busch-Petersen, J. Org. Chem. 1998, 63, 5971-5976;
49. f) R. R. Akhmetavaleev, G. M. Baibulatov, I. F. Nuriev, M. S. Miftakhov, Russ. J. Org. Chem. 2001, 37, 1079-1082;
50. g) R. R. Akhmetavaleev, G. M. Baibulatov, I. F. Nuriev, O. V. Shitikova, M. S. Miftakhov, Russ. J. Org. Chem. 2001, 37, 1083-1087;
51. h) E. Roulland, C. Monneret, J.-C. Florent, J. Org. Chem. 2002, 67, 4399-4406;
52. C. Kuhn, L. Skaltsuounis, C. Monneret, J.-C. Florent, Eur. J. Org. Chem. 2003, 2585-2595, and references therein.
53. H. Tanaka, T. Hasegawa, M. Iwashima, K. Iguchi, T. Takahashi, Org. Lett. 2004, 6, 1103-1106.
54. H. Tanaka, M. Kitade, M. Iwashima, K. Iguchi, T. Takahashi, Bioorg. Med. Chem. Lett. 2004, 14, 837-840.
55. L. A. Thompson, J. A. Ellman, Tetrahedron Lett. 1994, 35, 9333-9336.
56. a) A. Suzuki, N. Miyaura, T. Ishikawa, H. Sasaki, M. Ishikawa, M. Satoh, J. Am. Chem. Soc. 1989, 111, 314-321;
57. b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
58. a) M. Ishiyama, Y. Miyamoto, K. Sasamoto, Y. Ohkura, K. Ueno, Talanta 1997, 44, 1299;
59. b) H. Tominaga, M. Ishiyama, F. Ohseto, K. Sasamoto, T. Hamamoto, T. K. Suzuki, M. Watanabe, Anal. Commun. 1999, 36, 47-50.