Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 4, 2010, Pages 1676-1683

  Ulrich, Natalie C ^a   Kodet, John G ^a   Mente, Nolan R ^a   Kuder, Craig H ^b   Beutler, John A ^c   Hohl, Raymond J ^b   Wiemer, David F ^a,b  

^a E11 SSH   (United States)

^b UNIVERSITY OF IOWA   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Anti proliferative; Bioassay; Schweinfurthin; Stilbene; Synthesis

Indexed keywords

3 DEOXYSCHWEINFURTHIN B; ALKENE DERIVATIVE; ANTINEOPLASTIC AGENT; SCHWEINFURTHIN A; SCHWEINFURTHIN B; SCHWEINFURTHIN DERIVATIVE; SCHWEINFURTHIN F; SCHWEINFURTHIN G; UNCLASSIFIED DRUG;

ADENOCARCINOMA; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CHROMATOGRAPHY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; GLIOBLASTOMA; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; HYDROPHOBICITY; OLEFINATION; STRUCTURE ACTIVITY RELATION;

CELL DIVISION; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR PROBES; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STILBENES;

EID: 75849156898     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.12.063     Document Type: Article

References (26)

1. Stupp R., Mason W.P., van den Bent M.J., Weller M., Fisher B., Taphoorn M.J.B., Belanger K., Brandes A.A., Marosi C., Bogdahn U., Curschmann J., Janzer R.C., Ludwin S.K., Gorlia T., Allgeier A., Lacombe D., Cairncross J.G., Eisenhauer E., and Mirimanoff R.O. N. Engl. J. Med. 352 (2005) 987
2. Adamson C., Kanu O.O., Mehta A.I., Di C., Lin N., Mattox A.K., and Bigner D.D. Expert Opin. Invest. Drugs 18 (2009) 1061
3. Cragg G., and Newman D. Phytochem. Rev. 8 (2009) 313
4. Beutler J.A., Shoemaker R.H., Johnson T., and Boyd M.R. J. Nat. Prod. 61 (1998) 1509
5. Beutler J.A., Jato J., Cragg G.M., and Boyd M.R. Nat. Prod. Lett. 14 (2000) 399
6. Yoder B.J., Cao S., Norris A., Miller J.S., Ratovoson F., Razafitsalama J., Andriantsiferana R., Rasamison V.E., and Kingston D.G.I. J. Nat. Prod. 70 (2007) 342
7. Weinstein J.N., Myers T.G., O'Connor P.M., Friend S.H., Fornace Jr. A.J., Kohn K.W., Fojo T., Bates S.E., Rubinstein L.V., Anderson N.L., Buolamwini J.K., van Osdol W.W., Monks A.P., Scudiero D.A., Sausville E.A., Zaharevitz D.W., Bunow B., Viswanadhan V.N., Johnson G.S., Wittes R.E., and Paull K.D. Science 275 (1997) 343
8. Rabow A.A., Shoemaker R.H., Sausville E.A., and Covell D.G. J. Med. Chem. 45 (2002) 818
9. Pettit G.R., Inoue M., Kamano Y., Herald D.L., Arm C., Dufresne C., Christie N.D., Schmidt J.M., Doubek D.L., and Krupa T.S. J. Am. Chem. Soc. 110 (1988) 2006
10. McCormick J.L., McKee T.C., Cardellina J.H., Leid M., and Boyd M.R. J. Nat. Prod. 59 (1996) 1047
11. Mimaki Y., Kuroda M., Kameyama A., Sashida Y., Hirano T., Oka K., Maekawa R., Wada T., Sugita K., and Beutler J.A. Bioorg. Med. Chem. Lett. 7 (1997) 633
12. Treadwell E.M., Cermak S.C., and Wiemer D.F. J. Org. Chem. 64 (1999) 8718
13. Neighbors J.D., Beutler J.A., and Wiemer D.F. J. Org. Chem. 70 (2005) 925
14. Mente N.R., Wiemer A.J., Neighbors J.D., Beutler J.A., Hohl R.J., and Wiemer D.F. Bioorg. Med. Chem. Lett. 17 (2007) 911
15. Mente N.R., Neighbors J.D., and Wiemer D.F. J. Org. Chem. 73 (2008) 7963
16. Topczewski J.J., Neighbors J.D., and Wiemer D.F. J. Org. Chem. 74 (2009) 6965
17. Neighbors J.D., Salnikova M.S., Beutler J.A., and Wiemer D.F. Bioorg. Med. Chem. 14 (2006) 1771
18. Hollinshead S.P., Nichols J.B., and Wilson J.W. J. Org. Chem. 59 (1994) 6703
19. Falck J.R., Reddy K.K., and Chandrasekhar S. Tetrahedron Lett. 38 (1997) 5245
20. Wang, B.; Zhang, Y.-K.; Chen, J.; Zhang, W.; Song, J.; Del, B. U.; Brown, L.; Miller, G. European Patent WO03009807 (A2) 2003.
21. Sajiki H., and Hirota K. Tetrahedron 54 (1998) 13981
22. Howard T.T., Lingerfelt B.M., Purnell B.L., Scott A.E., Price C.A., Townes H.M., McNulty L., Handl H.L., Summerville K., Hudson S.J., Bowen J.P., Kiakos K., Hartley J.A., and Lee M. Bioorg. Med. Chem. 10 (2002) 2941
23. Hutchins R.O., Suchismita, Zipkin R.E., Taffer I.M., Sivakumar R., Monaghan A., and Elisseou E.M. Tetrahedron Lett. 30 (1989) 55
24. Pieters L., Van Dyck S., Gao M., Bai R., Hamel E., Vlietinck A., and Lemiere G. J. Med. Chem. 42 (1999) 5475
25. Roberti M., Pizzirani D., Simoni D., Rondanin R., Baruchello R., Bonora C., Buscemi F., Grimaudo S., and Tolomeo M. J. Med. Chem. 46 (2003) 3546
26. Pati H., Taherbhai Z., Forrest L., Wicks M., Bailey S., Staples A., Stewart M., Pennington W., Harris J., and Lee M. Lett. Drug Des. Discovery 1 (2004) 275