Synthesis and evaluation of a fluorescent ritterazine-cephalostatin hybrid

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5334-5337

  Kumar, Kanduluru Ananda ^a   La Clair, James J ^b   Fuchs, Philip L ^a  

^a PURDUE UNIVERSITY   (United States)

^b Xenobe Research Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYE; PHENAZINE DERIVATIVE; SPIRO COMPOUND; STEROID;

ARTICLE; CELL STRAIN HCT116; CHEMICAL STRUCTURE; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

FLUORESCENT DYES; HCT116 CELLS; HUMANS; MOLECULAR STRUCTURE; PHENAZINES; SPIRO COMPOUNDS; STEROIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80054728053     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202139z     Document Type: Article

References (24)

1. Pettit, G. R.; Inoue, M.; Kamano, Y.; Herald, D. L.; Arm, C.; Dufresne, C.; Christie, N. D.; Schmidt, J. M.; Doubek, D. L.; Krupa, T. S. J. Am. Chem. Soc. 1988, 110, 2006-2007.
2. Fukuzawa, S.; Matsunaga, S.; Fusetani, N. J. Org. Chem. 1994, 59, 6164-6166.
3. Moser, B. R. J. Nat. Prod. 2008, 71, 487-491.
4. Flessner, T.; Jautelat, R.; Scholz, U.; Winterfeldt, E. Fortschr. Chem. Org. Naturst. 2004, 87, 1-80.
5. Lee, S.; LaCour, T. G.; Fuchs, P. L. Chem. Rev. 2009, 109, 2275-2314.
6. Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157-10158.
7. Fortner, K. C.; Kato, D.; Tanaka, Y.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 275-280.
8. Lee, S.; LaCour, T. G.; Fuchs, P. L. Chem. Rev. 2009, 109, 2275-314.
9. Phillips, S. T.; Shair, M. D. J. Am. Chem. Soc. 2007, 129, 6589-6598.
10. Rudy, A.; López-Antón, N.; Dirsch, V. M.; Vollmar, A. M. J. Nat. Prod. 2008, 71, 482-486.
11. Komiya, T.; Fusetani., T.; Matsunaga, S.; Kubo, A.; Kaye, F. J.; Kelley, J. M.; Tamura, K.; Yoshida, M.; Fukuoka, M.; Nakagawa, K. Cancer Chemother. Pharmacol. 2003, 51, 202-208.
12. Burgett, A. W.; Poulsen, T. B.; Wangkanont, K.; Anderson, D. R.; Kikuchi, C.; Shimada, K.; Okubo, S.; Fortner, K. C.; Mimaki, Y.; Kuroda, M.; Murphy, J. P.; Schwalb, D. J.; Petrella, E. C.; Cornella- Taracido, I.; Schirle, M.; Tallarico, J. A.; Shair, M. D. Nat. Chem. Biol. 2011, 7, 639-647.
13. Unpublished results with Prof. Peng Huang (M. D. Anderson). Unpublished studies with Dr. John Beutler (National Cancer Institute). Synthesis of 25-epi-ritterostatin GN1N will be reported in due course
14. LaCour, T. G.; Guo, C.; Ma, S.; Jeong, J. U.; Boyd, M. R.; Matsunaga, S.; Fusetani, N.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1999, 9, 2587-2592.
15. Guo, C.; LaCour, T. G.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1999, 9, 419-424.
16. Yu, W. L.; Guizzunti, G.; Foley, T. L.; Burkart, M. D.; La Clair, J. J. J. Nat. Prod. 2010, 73, 1659-1666.
17. Hughes, C. C.; MacMillan, J. B.; Gaudêncio, S. P.; Fenical, W.; La Clair, J. J. Angew. Chem., Int. Ed. 2009, 48, 728-732.
18. Alexander, M. D.; Burkart, M. D.; Leonard, M. S.; Portonovo, P.; Liang, B.; Ding, X.; Joullié, M. M.; Gulledge, B. M.; Aggen, J. B.; Chamberlin, A. R.; Sandler, J.; Fenical, W.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H. R.; Evans, P. A.; Richardson,A. D.; Harper, M. K.; Ireland, C. M.; Vong, B. G.; Brady, T. P.; Theodorakis, E. A.; La Clair, J. J. ChemBioChem 2006, 7, 409-416.
19. Activities were measured using the protocols described in: Kang, M.; Jones, B. D.; Mandel, A. L.; Hammons, J. C.; DiPasquale, A. G.; Rheingold, A. L.; La Clair, J. J.; Burkart, M. D. J. Org. Chem. 2009, 74, 9054-9061.
20. Forsyth, C. J.; Ying, L.; Chen, J.; La Clair, J. J. J. Am. Chem. Soc. 2006, 128, 3858-3859.
21. See examples: La Clair, J. J. Nat. Prod. Rep. 2010, 27, 969-995.
22. Suzuki, K. Chem. Rec. 2010, 10, 291-307.
23. Meunier, B. Acc. Chem. Res. 2008, 41, 69-77.
24. Ellenberg, J.; Siggia, E. D.; Moreira, J. E.; Smith, C. L.; Presley, J. F.; Worman, H. J.; Lippincott-Schwartz, J. J. Cell. Biol. 1997, 138, 1193-1206.