Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 6, 2009, Pages 2282-2289

  Paterson, Ian ^a   Gardner, Nicola M ^a   Guzmán, Esther ^b   Wright, Amy E ^b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b FLORIDA ATLANTIC UNIVERSITY   (United States)

Author keywords

Antitumour; Macrolide; Total synthesis; Tubulin

Indexed keywords

2,3 DIHYDRODICTYOSTATIN; 2,3 DIHYDROISODICTYOSTATIN; 2,3,4,5 TETRAHYDRODICTYOSTATIN; 2,3,4,5 TETRAHYDROISODICTYOSTATIN; 6 NORDICTYOSTATIN; ALDEHYDE; ANTINEOPLASTIC AGENT; DICTYOSTATIN; DICTYOSTATIN DERIVATIVE; DISCODERMOLIDE; ISODICTYOSTATIN DERIVATIVE; MACROLIDE; NATURAL PRODUCT; PACLITAXEL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CHEMICAL REACTION; CULTURE MEDIUM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOLERABILITY; HUMAN; HUMAN CELL; IC 50; LACTONIZATION; MICROTUBULE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MACROLIDES; MODELS, MOLECULAR; SPECTRUM ANALYSIS;

EID: 62149085931     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.10.084     Document Type: Article

References (45)

1. Bergstralh D.T., and Ting J.P.Y. Cancer Treat. Rev. 32 (2006) 166
2. Kavallaris M., Verrills N.M., and Hill B.T. Drug Resist. Updat. 4 (2001) 392
3. Kuppens I.E.L.M. Curr. Clin. Pharmacol. 1 (2006) 57
4. Altmann K.H., and Gertsch J. Nat. Prod. Rep. 24 (2007) 327
5. http://www.fda.gov/bbs/topics/NEWS/2007/NEW01732.html.
6. Pettit G.R., Cichacz Z.A., Gao F., Boyd M.R., and Schmidt J.M. J. Chem. Soc., Chem. Commun. 9 (1994) 1111
7. Isbrucker R.A., Cummins J., Pomponi S.A., Longley R.E., and Wright A.E. Biochem. Pharmacol. 66 (2003) 75
8. Paterson I., Britton R., Delgado O., and Wright A.E. Chem. Commun. (2004) 632
9. Paterson I., Britton R., Delgado O., Meyer A., and Poullennec K.G. Angew. Chem. Int. Ed. 43 (2004) 4629
10. Shin Y., Fournier J.H., Fukui Y., Bruckner A.M., and Curran D.P. Angew. Chem. Int. Ed. 43 (2004) 4634
11. Shin Y., Fournier J.H., Bruckner A., Madiraju C., Balachandran R., Raccor B.S., Edler M.C., Hamel E., Sikorski R.P., Vogt A., Day B.W., and Curran D.P. Tetrahedron 63 (2007) 8537
12. Madiraju C., Edler M.C., Hamel E., Raccor B.S., Balachandran R., Zhu G., Giuliano K.A., Vogt A., Shin Y., Fournier J.H., Fukui Y., Brückner A.M., Curran D.P., and Day B.W. Biochemistry 44 (2005) 15053
13. Buey R.M., Barasoain I., Jackson E., Meyer A., Giannakakou P., Paterson I., Mooberry S., Andreu J.M., and Diaz J.F. Chem. Biol. 12 (2005) 1269
14. Paterson I., Gardner N.M., Poullennec K.G., and Wright A.E. Bioorg. Med. Chem. Lett. 17 (2007) 2443
15. Shin Y., Fournier J.H., Balachandran R., Madiraju C., Raccor B.S., Zhu G., Edler M.C., Hamel E., Day B.W., and Curran D.P. Org. Lett. 7 (2005) 2873
16. Paterson I., Gardner N.M., Poullennec K.G., and Wright A.E. J. Nat. Prod. 71 (2008) 364
17. Shin Y., Choy N., Balachandran R., Madiraju C., Day B.W., and Curran D.P. Org. Lett. 4 (2002) 4443
18. Fukui Y., Bruckner A.M., Shin Y., Balachandran R., Day B.W., and Curran D.P. Org. Lett. 8 (2006) 301
19. Paterson I., and Gardner N.M. Chem. Commun. (2007) 49
20. Jung W.H., Harrison C., Shin Y., Fournier J.H., Balachandran R., Raccor B.S., Sikorski R.P., Vogt A., Curran D.P., and Day B.W. J. Med. Chem. 50 (2007) 2951
21. Raccors B.S., Vogt A., Sikorski R.P., Madiraju C., Balachandran R., Montgomery K., Shin Y., Fukui Y., Jung W.H., Curran D.P., and Day B.W. Mol. Pharmacol. 73 (2008) 718
22. Canales A., Matesanz R., Gardner N.M., Andreu J.M., Paterson I., Díaz F., and Jiménez-Barbero J. Chem. Eur. J. 14 (2008) 7557
23. Florence G.J., Gardner N.M., and Paterson I. Nat. Prod. Rep. 25 (2008) 342
24. Paterson I., and Florence G.J. Eur. J. Org. Chem. (2003) 2193
25. Smith III A.B., and Freeze S.B. Tetrahedron 64 (2008) 261
26. For a preliminary account of this work, See:. Paterson I., Gardner N.M., Guzman E., and Wright A.E. Biorg. Med. Chem. Lett. 18 (2008) 10.1016/j.bmcl.2008.09.109
27. Ficini J., Claude B., Desmaele D., and Ouerfelli O. Heterocycles 25 (1987) 329
28. Schlaus S.E., Brandes B.D., Larrow J.F., Tokunaga M., Hansen K.B., Gould A.E., Furrow M.E., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 1307
29. 1H NMR analysis of the Mosher ester derivatives of alcohol 15.
30. Takai K., Nitta K., and Utimoto K. J. Am. Chem. Soc. 108 (1986) 7408
31. Devos A., Remion J., Frisque-Hesbain A.M., Colens A., and Ghosez L. J. Chem. Soc., Chem. Commun. (1979) 1180
32. Still W.C., and Gennari C. Tetrahedron Lett. 24 (1983) 4405
33. Paterson I., and Lyothier I. Org. Lett. 6 (2004) 4933
34. Evans D.A., Chapman K.T., and Carreira E.M. J. Am. Chem. Soc. 110 (1988) 3560
35. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551
36. Allred G.D., and Liebeskind L.S. J. Am. Chem. Soc. 118 (1996) 2748
37. Inanaga J., Hirata K., Saeki H., Katsuki T., and Yamaguchi M. Bull. Chem. Soc. Jpn. 52 (1979) 1989
38. Attempts to model the conformational effects of saturation of the C1-C5 region relative to the global energy minimum conformer of dictyostatin (Ref. 6) were complicated by the increased degree of rotational freedom associated with the C2-C5 carbon chain.
39. Bowden K., Heilbron I.M., and Jones E.R.H. J. Chem. Soc. (1946) 39
40. Chatterjee A.K., Choi T.L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360
41. Hong S.H., Sanders D.P., Lee C.W., and Grubbs R.H. J. Am. Chem. Soc. 127 (2005) 17160
42. Without the AcOH additive, the cross-metathesis reaction proceeded only in low yield (ca. 10%). It is proposed that the in situ generation of ruthenium hydride facilitates olefin isomerisation, preventing the metathesis proceeding. See:. Hong S.H., Wenzel A.G., Salguero T.T., Day M.W., and Grubbs R.H. J. Am. Chem. Soc. 129 (2007) 7961
43. 2 and MeOH) before the oxidation sequence.
44. Translactonisation has been avoided previously by employing anhydrous deprotection conditions using HF·pyridine. The increased reactivity of the saturated lactones to transacylation may be responsible for the reappearance of these isodictyostatin by-products.
45. Gunasekera S.P., Zuleta I.A., Longley R.E., Wright A.E., and Pomponi S.A. J. Nat. Prod. 66 (2003) 1615