Synthesis and SAR of C12-C13-oxazoline derivatives of epothilone A

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 14, 2009, Pages 3760-3763

  Pfeiffer, Bernhard ^a   Hauenstein, Kurt ^a   Merz, Philipp ^a   Gertsch, Jürg ^a   Altmann, Karl Heinz ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Anticancer; Epothilone; Natural product; SAR; Tubulin

Indexed keywords

EPOTHILONE A; OXAZOLINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; DRUG EFFECT; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MICROTUBULE ASSEMBLY; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; COMPUTER SIMULATION; EPOTHILONES; HUMANS; OXAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUBULIN MODULATORS;

EID: 67649643694     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.04.112     Document Type: Article

References (26)

1. Höfle G., and Reichenbach H. In: Cragg G.M., Kingston D.G.I., and Newman D.J. (Eds). Anticancer Agents from Natural Products (2005), CRC, Boca Raton 413-450
2. Gerth K., Bedorf N., Höfle G., Irschik H., and Reichenbach H. J. Antibiot. 49 (1996) 560
3. For the discovery of the microtubule-stabilizing properties of epothilones see:. Bollag D.M., McQueney P.A., Zhu J., Hensens O., Koupal L., Liesch J., Goetz M., Lazarides E., and Woods C.M. Cancer Res. 55 (1995) 2325
4. Altmann K.-H., Wartmann M., and O'Reilly T. Biochim. Biophys. Acta Rev. Cancer 1470 (2000) M79
5. Kowalski R.J., Giannakakou P., and Hamel E. J. Biol. Chem. 272 (1997) 2534
6. For reviews on the epothilone SAR see, e.g.:. Altmann K.-H., Pfeiffer B., Arseniyadis S., Pratt B.A., and Nicolaou K.C. ChemMedChem. 2 (2007) 396
7. Ref. 1a.
8. Rivkin A., Chou T.C., and Danishefsky S.J. Angew. Chem., Int. Ed. 44 (2005) 2838
9. Wartmann M., and Altmann K.-H. Curr. Med. Chem: Anti-Cancer Agents 2 (2002) 123
10. Nicolaou K.C., Roschangar F., and Vourloumis D. Angew. Chem., Int. Ed. 37 (1998) 2014
11. Kaminskas E., Jiang X., Aziz R., Bullock J., Kasliwal R., Harapanhalli R., Pope S., Sridhara R., Leighton J., Booth B., Dagher R., Justice R., and Pazdur R. Clin. Cancer Res. 14 (2008) 4378
12. Nicolaou K.C., Winssinger N., Pastor J., Ninkovic S., Sarabia F., He Y., Vourloumis D., Yang Z., Li T., Giannakakou P., and Hamel E. Nature 387 (1997) 268
13. Nicolaou K.C., Vourloumis D.T., Li H., Pastor J., Winssinger N., He Y., Ninkovic S., Sarabia F., Vallberg H., Roschangar F., King N.P., Finlay M.R.V., Giannakakou P., Verdier-Pinard P., and Hamel E. Angew. Chem., Int. Ed. 36 (1997) 2097
14. Su D.-S., Meng D., Bertinato P., Balog A., Sorensen E.J., Danishefsky S.J., Zheng Y.-H., Chou T.-C., He L., and Horwitz S.B. Angew. Chem., Int. Ed. 36 (1997) 757
15. Meng D.F., Su D.S., Balog A., Bertinato P., Sorensen E.J., Danishefsky S.J., Zheng Y.H., Chou T.C., He L.F., and Horwitz S.B. J. Am. Chem. Soc. 119 (1997) 2733
16. Su D.-S., Balog A., Meng D.F., Bertinato P., Danishefsky S.J., Zheng Y.-H., Chou T.-C., He L.F., and Horwitz S.B. Angew. Chem., Int. Ed. 36 (1997) 2093
17. Glunz P.W., He L., Horwitz S.B., Chakravarty S., Ojima I., Chou T.C., and Danishefsky S.J. Tetrahedron Lett. 40 (1999) 6895
18. Altmann K.-H., Bold G., Caravatti G., End N., Flörsheimer A., Guagnano V., O'Reilly T., and Wartmann M. Chimia 54 (2000) 612
19. Sefkow M., Kiffe M., and Höfle G. Bioorg. Med. Chem. Lett. 8 (1998) 3031
20. For details see Supplementary data.
21. Regueiro-Ren A., Borzilleri R.M., Zheng X., Kim S.-H., Johnson J.A., Fairchild C.R., Lee F.Y.F., Long B.H.G., and Vite D. Org. Lett. 3 (2001) 2693
22. Glide, version 4.5, Schrödinger, LLC, New York, NY, 2007.
23. Nettles J.H., Li H., Cornett B., Krahn J.M., Snyder J.P., and Downing K.H. Science 305 (2004) 866
24. Details of the computational protocols can be found in Supplementary data.
25. Nogales E., Wolf S.G., and Downing K.-H. Nature 391 (1998) 199
26. Maestro, version 8.0, Schrödinger, LLC, New York, NY, 2007.