The synthesis of 2-oxyalkyl-cyclohex-2-enones, related to the bioactive natural products COTC and antheminone A, which possess anti-tumour properties

Tetrahedron

Volumn 66, Issue 46, 2010, Pages 9049-9060

  Arthurs, Claire L ^a   Morris, Gareth A ^a   Piacenti, Michela ^a   Pritchard, Robin G ^a   Stratford, Ian J ^a   Tatic, Tanja ^a   Whitehead, Roger C ^a   Williams, Katharine F ^a   Wind, Natasha S ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

(2 CROTONYLOXYMETHYL) 6 FLUORO 4,5 (DIHYDROXY) CYCLOHEX 2 EN 1 ONE; 2 (CROTONYLOXYMETHYL) 4 HYDROXYCYCLOHEX 2 EN 1 ONE 4 OL; 2 CROTONYLOXYMETHYL 4,5,6 TRIHYDROXY 2 CYCLOHEXENONE; 2 CROTONYLOXYMETHYL 5,6 CYCLOPROPYL CYCLOHEX 2 EN 1 ONE 4 OL; 2(CROTONYLOXYMETHYL) 4,5 (DIHYDROXY) CYCLOHEX 2 EN 1 ONE; ANTHEMINONE A; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONCENTRATION RESPONSE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; LUNG NON SMALL CELL CANCER; PRIORITY JOURNAL;

EID: 77958162170     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.08.072     Document Type: Article

References (40)

1. T. Takeuchi, H. Chimura, M. Hamada, H. Umezawa, O. Yoshioka, N. Oguchi, Y. Takahashi, and A. Matsuda J. Antibiot. 28 1975 737
2. G. Bach, M.S. Breiding, S. Grabley, P. Hammann, K. Hütter, R. Thiericke, H. Uhr, J. Wink, and A. Zeeck Liebigs Ann. Chem. 1993 241
3. Y.Q. Tang, C. Maul, R. Höfs, I. Sattler, S. Gabley, X.-Z. Feng, A. Zeeck, and R. Thiericke Eur. J. Org. Chem. 1 2001 149
4. F. Collu, L. Bonsignore, M. Casu, C. Floris, J. Gertsch, and F. Cottiglia Bioorg. Med. Chem. Lett. 18 2008 1559
5. M. McNally, and J.R. Capon J. Nat. Prod. 64 2001 645
6. O. Aghil, M.C. Bibby, S.J. Carrington, J. Double, K.T. Douglas, R.M. Phillips, and T.K.M. Shing Anti-Cancer Drug Des. 7 1992 67
7. D.S. Hamilton, Z. Ding, B. Ganem, and D.J. Creighton Org. Lett. 4 2002 1209
8. E. Joseph, J.L. Eiseman, D.S. Hamilton, H. Wang, H. Tak, Z. Ding, B. Ganem, and D.J. Creighton J. Med. Chem. 46 2003 194
9. K.T. Douglas, and S. Shinkai Angew. Chem., Int. Ed. Engl. 24 1985 31
10. C.L. Arthurs, J. Raftery, H.L. Whitby, R.C. Whitehead, N. Wind, and I.J. Stratford Bioorg. Med. Chem. Lett. 17 2007 5974
11. C.L. Arthurs, N.S. Wind, R.C. Whitehead, and I.J. Stratford Bioorg. Med. Chem. Lett. 17 2007 553
12. C.L. Arthurs, K.F. Lingley, M. Piacenti, I.J. Stratford, T. Tatic, R.C. Whitehead, and N.S. Wind Tetrahedron Lett. 49 2008 2410
13. D. Basavaiah, and T. Satynarayana Chem. Rev. 103 2003 811
14. J.E. Audia, L. Boisvert, A.D. Patten, A. Villalobos, and S.J. Danishefsky J. Am. Chem. Soc. 54 1989 3738
15. D. Mercier, J. Leboul, J. Cléophax, and S.D. Géro Carbohydr. Res. 20 1971 299
16. J. Schultz, M.W. Beaton, and D. Gani J. Chem. Soc., Perkin Trans. 1 2000 943
17. F. Rezgui, and M.M. El Gaied Tetrahedron Lett. 39 1998 5965
18. J.-E. Bäckvall, S.E. Byström, and R.E. Nordberg J. Org. Chem. 49 1984 4619
19. R.J. Kazlauskas, A.N.E. Weissfloch, A.T. Rappaport, and L.A. Cuccia J. Org. Chem. 56 1991 2656
20. D.R. Deardorff, A.J. Matthews, D.S. McMeekin, and C.L. Craney Tetrahedron Lett. 27 1986 1255
21. W.P. Griffith, S.V. Ley, G.P. Whitcombe, and A.D. White J. Chem. Soc., Chem. Commun. 1987 1625
22. O. Gebauer, and R. Brückner Liebigs Ann. 1996 1559
23. J.-L. Montchamp, F. Tian, M.E. Hart, and J.W. Frost J. Org. Chem. 61 1996 3897
24. N.L. Douglas, S.V. Ley, H.M.I. Osborn, D.R. Owen, H.W.M. Priepke, and S.L. Warriner Synlett 1996 793
25. Y.-L. Zhong, and T.K.M. Shing J. Org. Chem. 62 1997 2622
26. H.M.R. Hoffmann, and J. Rabe Angew. Chem., Int. Ed. Engl. 22 1983 795
27. A. Porzelle, C.M. Williams, B.D. Schwartz, and I.R. Gentle Synlett 2005 2923
28. L.M. Murray, P. O'Brien, and R.J.K. Taylor Org. Lett. 5 2003 1943
29. R.E. Banks J. Fluorine Chem. 87 1998 1
30. J. Chaykovsky, and E.J. Corey J. Am. Chem. Soc. 87 1965 1353
31. R.A. Battey, and W.B. Motherwell Tetrahedron Lett. 32 1991 6211
32. S. Luo, P.G. Wang, and J.-P. Chen J. Org. Chem. 69 2004 555
33. N. Robertson, A. Haigh, G.E. Adams, and I.J. Stratford Eur. J. Cancer 30A 1994 1013
34. J. Carmichael, W.G. DeGraff, A.F. Gazdar, J.D. Minna, and J.B. Mitchell Cancer Res. 47 1987 936
35. C. Colas, B. Quiclet-Sire, J. Cléophax, J. Delaumény, A. Sepulchre, and S.D. Géro J. Am. Chem. Soc. 102 1980 857
36. L. Begum, J.M. Box, M.G.B. Drew, L.M. Harwood, J.L. Humphreys, D.J. Lowes, G.A. Morris, P.M. Redon, F.M. Walker, and R.C. Whitehead Tetrahedron 59 2003 4827
37. M.T. Barros, C.D. Maycock, and M.R. Ventura J. Chem. Soc., Perkin Trans. 1 2001 166
38. G.M. Sheldrick Acta Crystallogr. A64 2008 112
39. N. Robertson, I.J. Stratford, S. Houlbrook, J. Carmichael, and G.E. Adams Biochem. Pharmacol. 44 1992 409
40. T. Mosmann J. Immunol. Methods 65 1983 55