Synthesis and biological activities of the tris-oxazole macrolactone analogs of mycalolides

Tetrahedron

Volumn 68, Issue 42, 2012, Pages 8753-8760

  Kita, Masaki ^a   Oka, Hirotaka ^a   Usui, Akihiro ^a   Ishitsuka, Tomoya ^a   Mogi, Yuzo ^a   Watanabe, Hidekazu ^a   Kigoshi, Hideo ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Actin depolymerization; Antimycotic activity; Natural products; Ring closing metathesis; Structure activity relationships

Indexed keywords

ANTIFUNGAL AGENT; MACROLIDE; MYCALOLIDE B; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; BIOLOGICAL ACTIVITY; CANDIDA ALBICANS; CHEMICAL REACTION; CONJUGATION; CYTOTOXICITY; DENSITY FUNCTIONAL THEORY; DEPOLYMERIZATION; DRUG SYNTHESIS; FEMALE; HELA CELL; HUMAN; HUMAN CELL; HYDROGEN BOND; OXIDATION; PHARMACOPHORE; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; TRICHOPHYTON MENTAGROPHYTES; TUMOR CELL;

FUNGI; MYCALE;

EID: 84865736239     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.08.012     Document Type: Article

References (53)

1. N. Fusetani, K. Yasumuro, S. Matsunaga, and K. Hashimoto Tetrahedron Lett. 30 1989 2809 2812
2. S. Wada, S. Matsunaga, S. Saito, N. Fusetani, and S. Watabe J. Biochem. 123 1998 946 952
3. S. Matsunaga, P. Liu, C.A. Celatka, J.S. Panek, and N. Fusetani J. Am. Chem. Soc. 121 1999 5605 5606
4. P. Phuwapraisirisan, S. Matsunaga, R.W.M. van Soest, and N. Fusetani J. Nat. Prod. 65 2002 942 943
5. S. Tsukamoto, K. Koimaru, and T. Ohta Mar. Drugs 3 2005 29 35
6. M. Hori, S. Saito, Y. Shin, H. Ozaki, N. Fusetani, and H. Karaki FEBS Lett. 322 1993 151 154
7. S. Saito, S. Watabe, H. Ozaki, N. Fusetani, and H. Karaki J. Biol. Chem. 269 1994 29710 29714
8. S. Matsunaga, T. Sugawara, and N. Fusetani J. Nat. Prod. 61 1998 1164 1167
9. M.A. Rashid, K.R. Gustafson, J.H. Cardeilina II, and M.R. Boyd J. Nat. Prod. 58 1995 1120 1125
10. J. Kubanek, P.R. Jensen, P.A. Keifer, M.C. Sullards, D.O. Collins, and W. Fenical Proc. Natl. Acad. Sci. U.S.A. 100 2003 6916 6921
11. J.A. Roesener, and P.J. Scheuer J. Am. Chem. Soc. 108 1986 846 847
12. S. Matsunaga, N. Fusetani, K. Hashimoto, K. Koseki, M. Noma, H. Noguchi, and U. Sankawa J. Org. Chem. 54 1989 1360 1363
13. M.R. Kernan, T.F. Molinski, and D.J. Faulkner J. Org. Chem. 53 1988 5014 5020
14. S.-C. Chung, S.-H. Lee, K.H. Jang, W. Park, J.-E. Jeon, H. Oh, J. Shin, and K.-B. Oh Bioorg. Med. Chem. Lett. 21 2011 3198 3201
15. J. Kobayashi, O. Murata, and H. Shigemori J. Nat. Prod. 56 1993 787 791
16. S. Matsunaga, N. Fusetani, and K. Hashimoto J. Am. Chem. Soc. 108 1986 847 849
17. J. Tanaka, Y. Yan, J. Choi, J. Bai, V.A. Klenchin, I. Rayment, and G. Marriott Proc. Natl. Acad. Sci. U.S.A. 100 2003 13851 13856
18. V.A. Klenchin, J.S. Allingham, R. King, J. Tanaka, G. Marriott, and I. Rayment Nat. Struct. Biol. 10 2003 1058 1063
19. J.S. Allingham, J. Tanaka, G. Marriott, and I. Rayment Org. Lett. 6 2004 597 599
20. K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, and M. Arakawa J. Am. Chem. Soc. 115 1993 11020 11021
21. M. Ojika, H. Kigoshi, T. Ishigaki, I. Tsukada, T. Tsuboi, T. Ogawa, and K. Yamada J. Am. Chem. Soc. 116 1994 7441 7442
22. H. Kigoshi, K. Suenaga, T. Mutou, T. Ishigaki, T. Atsumi, H. Ishiwata, A. Sakakura, T. Ogawa, M. Ojika, and K. Yamada J. Org. Chem. 61 1996 5326 5351
23. K. Kitamura, T. Teruya, T. Kuroda, H. Kigoshi, and K. Suenaga Bioorg. Med. Chem. Lett. 19 2009 1896 1898
24. Ohno, O.; Morita, M.; Kitamura, K.; Teruya, T.; Kita, M.; Kigoshi, H.; Suenaga, K. submitted for publication.
25. K. Yamada, M. Ojika, H. Kigoshi, and K. Suenaga Nat. Prod. Rep. 26 2009 27 43
26. K. Yamada, M. Ojika, H. Kigoshi, and K. Suenaga Proc. Jpn. Acad. Ser. B 86 2010 176 189
27. M. Kita, Y. Hirayama, M. Sugiyama, and H. Kigoshi Angew. Chem., Int. Ed. 50 2011 9871 9874
28. M. Kita, K. Yoneda, Y. Hirayama, K. Yamagishi, Y. Saito, Y. Sugiyama, Y. Miwa, O. Ohno, M. Morita, K. Suenaga, and H. Kigoshi ChemBioChem 13 2012 1754 1758
29. T. Kuroda, K. Suenaga, A. Sakakura, T. Handa, K. Okamoto, and H. Kigoshi Bioconjugate Chem. 17 2006 524 529
30. K. Hirata, S. Muraoka, K. Suenaga, K. Kuroda, K. Kato, H. Tanaka, M. Yamamoto, M. Takata, K. Yamada, and H. Kigoshi J. Mol. Biol. 356 2006 945 954
31. K. Suenaga, N. Kamei, Y. Okugawa, M. Takagi, A. Akao, H. Kigoshi, and K. Yamada Bioorg. Med. Chem. Lett. 7 1997 269 274
32. H. Kigoshi, K. Suenaga, M. Takagi, A. Akao, K. Kanematsu, N. Kamei, Y. Okugawa, and K. Yamada Tetrahedron 58 2002 1075 1102
33. Reviews
34. K.-S. Yeung, and I. Paterson Angew. Chem., Int. Ed. 41 2002 4632 4653
35. S.K. Chattopadhyay, and G. Pattenden J. Chem. Soc., Perkin Trans. 1 2000 2429 2454 and references are therein
36. P. Liu, and J.S. Panek J. Am. Chem. Soc. 122 2000 1235 1236
37. J.S. Panek, and P. Liu J. Am. Chem. Soc. 122 2000 11090 11097
38. G. Pattenden, N.J. Ashweek, C.A.G. Baker-Glenn, G.M. Walker, and J.G.K. Yee Angew. Chem., Int. Ed. 46 2007 4359 4363
39. S.K. Chattopadhyay, and G. Pattenden Tetrahedron Lett. 39 1998 6095 6098
40. K. Suenaga, T. Kimura, T. Kuroda, K. Matsui, S. Miya, S. Kuribayashi, A. Sakakura, and H. Kigoshi Tetrahedron 62 2006 8278 8290
41. Kuroda, T. Ph.D. thesis, University of Tsukuba, 2008.
42. J. Maddock, G. Pattenden, and P.G. Wight J. Comput. Aided Mol. Des. 7 1993 573 586
43. T. Kimura, S. Kuribayashi, T. Sengoku, K. Matsui, S. Ueda, I. Hayakawa, K. Suenaga, and H. Kigoshi Chem. Lett. 36 2007 1490 1491
44. M. Kita, H. Watanabe, T. Ishitsuka, Y. Mogi, and H. Kigoshi Tetrahedron Lett. 51 2010 4882 4885
45. H. Jin, J. Uenishi, W.J. Christ, and Y. Kishi J. Am. Chem. Soc. 108 1986 5644 5646
46. K. Takai, M. Tagashira, T. Kuroda, K. Oshima, K. Utimoto, and H. Nozaki J. Am. Chem. Soc. 108 1986 6048 6050
47. Y. Okude, S. Hirano, T. Hiyama, and H. Nozaki J. Am. Chem. Soc. 99 1977 3179 3181
48. S. BouzBouz, and J. Cossy Org. Lett. 6 2004 3469 3472
49. A. Hafner, R.O. Duthaler, R. Marti, J. Rihs, P. Rothe-Streit, and F. Schwarzenbach J. Am. Chem. Soc. 114 1992 2321 2336
50. J.S. Kingsbury, J.P.A. Harrity, P.J. Bonitatebus, and A.H. Hoveyda J. Am. Chem. Soc. 121 1999 791 799
51. S.B. Garber, J.S. Kingsbury, B.L. Gray, and A.H. Hoveyda J. Am. Chem. Soc. 122 2000 8168 8179
52. An example of Z-preferential RCM reaction in hexane: B. Wang, and C.J. Forsyth Org. Lett. 8 2006 5223 5226
53. A. Ogawa, and D.P. Curran J. Org. Chem. 62 1997 450 451