Syntheses of structurally-simplified and fluorescently-labeled neovibsanin derivatives and analysis of their neurite outgrowth activity in PC12 cells

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 5, 2012, Pages 2089-2093

  Imagawa, Hiroshi ^a   Saijo, Hayato ^a   Yamaguchi, Hitomi ^a   Maekawa, Ken ^a   Kurisaki, Takahiro ^a   Yamamoto, Hirofumi ^a   Nishizawa, Mugio ^a   Oda, Masataka ^a   Kabura, Michiko ^a   Nagahama, Masahiro ^a   Sakurai, Jun ^a   Kubo, Miwa ^a   Nakai, Megumi ^a   Makino, Kosho ^a   Ogata, Mitsuko ^a   Takahashi, Hironobu ^a   Fukuyama, Yoshiyasu ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Fluorescent probe molecule; Neovibsanin derivative; Neurite outgrowth activity; PC12 cells; Structure activity correlation

Indexed keywords

DITERPENOID; FLUORESCENT DYE; NEOVIBSANIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CELL CULTURE; CELL FUNCTION; CELL STRAIN; CELL STRUCTURE; CONTROLLED STUDY; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NERVE FIBER GROWTH;

ANIMALS; DITERPENES; FLUORESCENT DYES; MODELS, MOLECULAR; NEURITES; NEUROGENESIS; NEURONS; PC12 CELLS; RATS; VIBURNUM;

EID: 84857367927     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.01.006     Document Type: Article

References (29)

1. Y. Fukuyama, H. Minami, K. Takeuchi, M. Kodama, and K. Kawazu Tetrahedron Lett. 37 1996 6767
2. Y. Fukuyama, and T.J. Esumi Org. Synth. Chem. Jpn. 65 2007 585
3. Y. Fukuyama, H. Minami, I. Yamamoto, M. Kodama, and K. Kawazu Chem. Pharm. Bull. 46 1998 545
4. M. Kubo, H. Minami, E. Hayashi, M. Kodama, K. Kawazu, and Y. Fukuyama Tetrahedron Lett. 40 1999 6261
5. M. Kubo, I.-S. Chen, and Y. Fukuyama Chem. Pharm. Bull. 49 2001 242
6. Y. Fukuyama, M. Kubo, H. Minami, H. Yuasa, A. Matsuo, T. Fujii, M. Morisaki, and K. Harada Chem. Pharm. Bull. 53 2005 72
7. Y. Fukuyama, H. Fujii, H. Minami, H. Takahashi, and M.J. Kubo Nat. Prod. 69 2006 1098
8. Y. Fukuyama, M. Kubo, T. Esumi, K. Harada, and H. Hioki Heterocycles 81 2010 1571
9. Y. Fykuyama, and M. Kubo Curr. Top. Phytochem. 10 2011 39
10. M.J. Gallen, and C.M. Williams Org. Lett. 10 2008 713
11. A.P.J. Chen, and C.M. Williams Org. Lett. 10 2008 3441
12. H. Imagawa, H. Saijo, T. Kurisaki, H. Yamamoto, M. Kubo, Y. Fukuyama, and M. Nishizawa Org. Lett. 11 2009 1253
13. T. Esumi, T. Mori, M. Zhao, M. Toyota, and Y. Fukuyama Org. Lett. 12 2010 888
14. G. Mehta, and B.A. Bhat Tetrahedron Lett. 50 2009 2474
15. R. Gatri, and M.M.E. Gaïed Tetrahedron Lett. 43 2002 7835
16. K. Koide, and C.T. Meta Org. Lett. 11 2004 1785
17. Crystallographic data (excluding structure factors) for the structures of 6 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 832773. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ UK (Fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
18. A.G. Lloyd, and S.T. Arthur Proc. Natl. Acad. Sci. U.S.A. 73 1976 2424
19. This position was numbered based on the natural neovibsanin skeleton.
20. A.B. Smith III, B.D. Dorsey, M. Ohba, A.T. Lupo Jr., and M.S.J. Malamas Org. Chem. 53 1988 4314
21. R. Gatri, M. Moncef, and E. Gaïed Tetrahedron Lett. 43 2002 7835
22. A mixture of stereoisomer at acetal position was used for the assay without separation.
23. An asymmetric version of this Diels-Alder reaction was recently reported. K.A. Ahrendt, C.J. Borths, and D.W.C. MacMillan J. Am. Chem. Soc. 122 2000 4243
24. N.S. Narasimhan, and R.S. Mali Synthesis 12 1975 796
25. In the previous synthetic study of neovibsanin B, we have found that 2-methoxy benzyl ether, which have a coordination ability, is advantageous for subsequent regioselective alkylation.
26. F. Guibe Tetrahedron 53 1997 13509
27. We developed this deprotection condition in previous total synthesis of 2 (Ref. 4a).
28. B.A. Hermanand, and S.M. Fernandez Biochem. Biophys. Res. Commun. 103 1981 1112
29. S. Goya, A. Takadate, H. Fujino, M. Otagiri, and K. Uekama Chem. Pharm. Bull. 30 1982 1363