Synthesis and biological evaluation of triazole analogues of antillatoxin

Tetrahedron

Volumn 67, Issue 35, 2011, Pages 6659-6672

  Goto, Ryosuke ^a   Okura, Ken ^a   Sakazaki, Hayato ^a   Sugawara, Tatsuya ^a   Matsuoka, Shigeru ^a   Inoue, Masayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Biological activity; Natural products; Neurotoxin; Structure activity relationship; Total synthesis

Indexed keywords

ALKYNE; ANTILLATOXIN; TRIAZOLE DERIVATIVE;

ANIMAL CELL; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; MOUSE; NEUROBLASTOMA CELL; NONHUMAN; PRIORITY JOURNAL;

EID: 79960955056     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.012     Document Type: Article

References (49)

1. J. Orjala, D.G. Nagle, V. Hsu, and W.H. Gerwick J. Am. Chem. Soc. 117 1995 8281
2. F. Yokokawa, H. Fujiwara, and T. Shioiri Tetrahedron Lett. 40 1999 1915 Total synthesis of (4S,5S), (4S,5R), (4R,5S)- and (4R,5R)-1
3. F. Yokokawa, H. Fujiwara, and T. Shioiri Tetrahedron 56 2000 1759 Total synthesis of (4S,5R)-1
4. F. Yokokawa, and T. Shioiri J. Org. Chem. 63 1998 8638
5. J.D. White, R. Hanselmann, and D.J. Wardrop J. Am. Chem. Soc. 121 1999 1106 Total synthesis of (4S,5S)- and (4R,5R)-1
6. K.-C. Lee, and T.-P. Loh Chem. Commun. 40 2006 4209
7. F. Yokokawa, and T. Shioiri J. Synth. Org. Chem. Jpn. 58 2000 634
8. Y. Hamada, and T. Shioiri Chem. Rev. 105 2005 4441
9. F.W. Berman, W.H. Gerwick, and T.F. Murray Toxicon 37 1999 1645
10. W.I. Li, F.W. Berman, T. Okino, F. Yokokawa, T. Shioiri, W.H. Gerwick, and T.F. Murray Proc. Natl. Acad. Sci. U.S.A. 98 2001 7599
11. W.A. Catterall Neuron 26 2000 13
12. S.-Y. Wang, and G.K. Wang Cell. Signalling 15 2003 151
13. W.A. Catterall, S. Cestele, V. Yarov-Yarovoy, F.H. Yu, K. Konoki, and T. Scheuer Toxicon 49 2007 124
14. Z. Cao, J. George, W.H. Gerwick, D.G. Baden, J.D. Rainier, and T.F. Murray J. Pharmacol. Exp. Ther. 326 2008 604
15. J.J. Clare, S.N. Tate, M. Nobbs, and M.A. Romanos Drug Discovery Today 5 2000 506
16. A. Al-Sabi, J. McArthur, V. Ostroumov, and R.J. French Mar. Drugs 4 2006 157
17. Gerwick and Shioiri reported that C4, C5-stereoisomers of 1, (4R,5S), (4S,5R), and (4S,5S)-analogues, were 25-fold to 55-fold less cytotoxic against Neuro 2a than the natural antillatoxin W.I. Li, B.L. Marquez, T. Okino, F. Yokokawa, T. Shioiri, W.H. Gerwick, and T.F. Murray J. Nat. Prod. 67 2004 559
18. K. Okura, S. Matsuoka, R. Goto, and M. Inoue Angew. Chem., Int. Ed. 49 2010 329
19. L.M. Nogle, T. Okino, and W.H. Gerwick J. Nat. Prod. 64 2001 983
20. H.K. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004
21. H.K. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128
22. G.C. Tron, T. Pirali, R.A. Billington, P.L. Canonico, G. Sorba, and A.A. Genazzani Med. Res. Rev. 28 2008 278
23. G. Lu, X. Li, W.L. Chan, and A.S.C. Chan Chem. Commun. 2002 172
24. G. Gao, D. Moore, R.-G. Xie, and L. Pu Org. Lett. 4 2002 4143
25. J.A. Marshall, and M.P. Bourbeau Org. Lett. 5 2003 3197
26. O. Mitsunobu Synthesis 1981 1
27. D.L. Hughes Org. React. 42 1992 335
28. S. Takano, S. Hatakeyama, and K. Ogasawara J. Chem. Soc., Chem. Commun. 1977 68
29. L.A. Carpino J. Am. Chem. Soc. 115 1993 4397
30. L.A. Carpino, and A. El-Faham J. Org. Chem. 59 1994 695
31. N. Bernard, F. Chemla, and J. Normant Eur. J. Org. Chem. 9 1999 2067
32. M. Kitamura, S. Shirakawa, and K. Maruoka Angew. Chem., Int. Ed. 44 2005 1549
33. T. Fukuyama, C.-K. Jow, and M. Cheung Tetrahedron Lett. 36 1995 6373
34. T. Kan, and T. Fukuyama Chem. Commun. 2004 353
35. J. Coste, E. Frerot, and P. Jouin J. Org. Chem. 59 1994 2437
36. J.F. Carson Synthesis 1981 268
37. E. Negishi, and T. Takahashi Synthesis 1988 1
38. H.P. Dang, and G. Linstrumelle Tetrahedron Lett. 1978 191
39. H.C. Brown, C. Subrahmanyam, T. Hamaoka, N. Ravindran, D.H. Bowman, S. Misumi, M.K. Unni, V. Somayaji, and N.G. Bhat J. Org. Chem. 54 1989 6068
40. S. De Murari, S. Frigerio, and M. Santagostino J. Org. Chem. 61 1996 9272
41. J.L. Luche J. Am. Chem. Soc. 100 1978 2226
42. I. Shiina, M. Kubota, and R. Ibuka Tetrahedron Lett. 43 2002 7535
43. I. Shiina, M. Kubota, H. Oshiumi, and M. Hashizume J. Org. Chem. 69 2004 1822
44. H. Lindlar Helv. Chim. Acta 35 1952 446
45. T. Jin, S. Kamijo, and Y. Yamamoto Eur. J. Org. Chem. 2004 3789
46. C.Z. Tao, X. Cui, J. Li, A.X. Liu, L. Liu, and Q.X. Guo Tetrahedron Lett. 48 2007 3525
47. A.K. Feldman, B. Colasson, and V.V. Fokin Org. Lett. 6 2004 3897
48. V.V. Rostovtsev, L.G. Green, V.V. Folkin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596
49. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057