New candidaspongiolides, tedanolide analogues that selectively inhibit melanoma cell growth

Organic Letters

Volumn 13, Issue 13, 2011, Pages 3518-3521

  Whitson, Emily L ^a   Pluchino, Kristen M ^b   Hall, Matthew D ^b   McMahon, James B ^a   McKee, Tawnya C ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CANDIDASPONGIOLIDE; MACROLIDE; TEDANOLIDE;

ARTICLE; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; HUMAN; MELANOMA; PATHOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; CELL PROLIFERATION; HUMANS; MACROLIDES; MELANOMA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79959715879     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201329p     Document Type: Article

References (16)

1. Soengas, M. S.; Lowe, S. W. Oncogene 2003, 22, 3138
2. Meragelman, T. L.; Willis, R. H.; Woldemichael, G. M.; Heaton, A.; Murphy, P. T.; Snader, K. M.; Newman, D. J.; van Soest, R.; Boyd, M. R.; Cardellina, J. H., II; McKee, T. C. J. Nat. Prod. 2007, 70, 1133
3. Schmitz, F. J.; Gunasekera, S. P.; Yalamanchili, G.; Hossain, M. B.; van der Helm, D. J. Am. Chem. Soc. 1984, 106, 7251
4. Fusetani, N.; Sugawara, T.; Matsunaga, S.; Hirota, H. J. Org. Chem. 1991, 56, 4971
5. Chevallier, C.; Bugni, T. S.; Feng, X.; Harper, M. K.; Orendt, A. M.; Ireland, C. M. J. Org. Chem. 2006, 71, 2510
6. Cheng, J. F.; Lee, J. S.; Sakai, R.; Jares-Erijman, E. A.; Silva, M. V.; Rinehart, K. L. J. Nat. Prod. 2007, 70, 332
7. Fleming, K. N.; Taylor, R. E. Angew. Chem., Int. Ed. 2004, 43, 1728
8. Perez, M.; del Pozo, C.; Reyes, F.; Rodriguez, A.; Francesch, A.; Echavarren, A. M.; Cuevas, C. Angew. Chem., Int. Ed. 2004, 43, 1724
9. 6.
10. There was no evidence of equilibrium isomers in the NMR data for the lipase-derived macrolide core reported previously. (2)
11. 3OD.
12. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791
13. Nishimura, S.; Matsunaga, S.; Yoshida, S.; Nakao, Y.; Hirota, H.; Fusetani, N. Bioorg. Med. Chem. 2005, 13, 455
14. Chen, K. G.; Valencia, J. C.; Gillet, J. P.; Hearing, V. J.; Gottesman, M. M. Pigment Cell Melanoma Res. 2009, 22, 740
15. Nishimura, S.; Matsunaga, S.; Yoshida, M.; Hirota, H.; Yokoyama, S.; Fusetani, N. Bioorg. Med. Chem. 2005, 13, 449
16. Trisciuoglio, D.; Uranchimeg, B.; Cardellina, J. H.; Meragelman, T. L.; Matsunaga, S.; Fustetani, N.; Del Bufalo, D.; Shoemaker, R. H.; Melillo, G. J. Natl. Cancer Inst. 2008, 100, 1233