Synthesis and biological evaluation of B-ring analogues of (-)-rhazinilam

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 7, 2006, Pages 2314-2332

  Décor, Anne ^a   Monse, Barbara ^a   Martin, Marie Thérèse ^a   Chiaroni, Angèle ^a   Thoret, Sylviane ^a   Guénard, Daniel ^a   Guéritte, Françoise ^a   Baudoin, Olivier ^a  

^a CNRS   (France)

Author keywords

Cytotoxicity; Rhazinilam; Structure activity relationships; Tubulin

Indexed keywords

1 (2 METHOXY)ETHOXYMETHYLRHAZINILAM; 1 (2 TRIMETHYLSILYL)ETHOXYMETHYLRHAZINILAM; 1 (4 METHOXYBENZOYL)RHAZINILAM; 1 (4 TOLUENESULFONYL)RHAZINILAM; 1 (4 TRIFLUOROMETHYLBENZOYL)RHAZINILAM; 1 ACETYLRHAZINILAM; 1 ALLYLRHAZINILAM; 1 BENZOYLRHAZINILAM; 1 BENZYLRHAZINILAM; 1 CYANOMETHYLRHAZINILAM; 1 ETHOXYCARBONYLRHAZINILAM; 1 METHANESULFONYLRHAZINILAM; 1 METHOXYMETHYLRHAZINILAM; 1 PERFLUORO TERT BUTOXYCARBONYLRHAZINILAM; 1 PHENOXYCARBONYLRHAZINILAM; 1 PIVALOYLRHAZINILAM; 1 PROPYLRHAZINILAM; 16 BENZOYLRHAZINILAM; 16 BENZYLRHAZINILAM; 16 ETHYLRHAZINILAM; 16 HYDROXYRHAZINILAM; 16 METHYLRHAZINILAM; 16 TERT BUTOXYCARBONYLRHAZINILAM; BENZOYLRHAZINILAM; CARBAMIC ACID; ETHYLRHAZINILAM; MACROCYCLIC COMPOUND; NATURAL PRODUCT; RHAZINILAM; TUBULIN; UNCLASSIFIED DRUG;

APOCYNACEAE; ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL; CELL GROWTH; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYTOTOXICITY; MICROTUBULE ASSEMBLY; MOLECULAR MODEL; PLANT PRODUCT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ALKALOIDS; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLIZINES; LACTAMS; MICROTUBULES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN;

APOCYNACEAE;

EID: 32844467971     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.11.011     Document Type: Article

References (32)

1. E. Hamel Med. Res. Rev. 16 1996 207 231
2. A. Jordan, J.A. Hadfield, N.J. Lawrence, and A.T. McGown Med. Res. Rev. 18 1998 259 296
3. J.A. Hadfield, S. Ducki, N. Hirst, and A.T. McGown Prog. Cell Cycle Res. 5 2003 309 325
4. T. Beckers, and S. Mahboobi Drugs Future 28 2003 767 785
5. O. Baudoin, and F. Guéritte Atta-ur-Rahman Studies in Natural Product Chemistry Vol. 29 2003 Elsevier 355 418
6. O. Baudoin, D. Guénard, and F. Guéritte Mini-Rev. Org. Chem. 1 2004 333 341
7. B. David, T. Sévenet, M. Morgat, D. Guénard, A. Moisand, Y. Tollon, O. Thoison, and M. Wright Cell Motil. Cytoskeleton 28 1994 317 326
8. J. Lévy, M. Soufyane, C. Mirand, M. Döé de Maindreville, and D. Royer Tetrahedron: Asymmetry 8 1997 4127 4133
9. B. David, T. Sévenet, O. Thoison, K. Awang, M. Païs, M. Wright, and D. Guénard Bioorg. Med. Chem. Lett. 7 1997 2155 2158
10. C. Dupont, D. Guénard, L. Tchertanov, S. Thoret, and F. Guéritte Bioorg. Med. Chem. 7 1999 2961 2969
11. J.-P. Alazard, C. Millet-Paillusson, D. Guénard, and C. Thal Bull. Soc. Chim. Fr. 133 1996 251 266
12. C. Pascal, J. Dubois, D. Guénard, and F. Guéritte J. Org. Chem. 63 1998 6414 6420
13. C. Pascal, J. Dubois, D. Guénard, L. Tchertanov, S. Thoret, and F. Guéritte Tetrahedron 54 1998 14737 14756
14. M.G. Banwell, A.J. Edwards, J. Smith, E. Hamel, and P. Verdier-Pinard J. Chem. Soc., Perkin Trans. 1 2000 1497 1499
15. M.G. Banwell, A.J. Edwards, K.A. Jolliffe, J.A. Smith, E. Hamel, and P. Verdier-Pinard Org. Biomol. Chem. 1 2003 296 305
16. E. Pasquinet, P. Rocca, S. Richalot, F. Guéritte, D. Guénard, A. Godard, F. Marsais, and G. Quéguiner J. Org. Chem. 66 2001 2654 2661
17. O. Baudoin, F. Claveau, S. Thoret, A. Herrbach, D. Guénard, and F. Guéritte Bioorg. Med. Chem. 10 2002 3395 3400
18. L. Cotarca, P. Delogu, A. Nardelli, and V. Sunjic Synthesis 1996 553 576
19. L.A. Carpino, B.J. Cohen, K.E. Stephens Jr., S.Y. Sadat-Aalaee, J.-H. Tien, and D.C. Langridge J. Org. Chem. 51 1986 3732 3734
20. S.-Y. Han, and Y.-A. Kim Tetrahedron 60 2004 2447 2467
21. For a related macrolactamization using TBTU/HOBT, see C. Hermann, C. Giammasi, A. Geyer, and M.E. Maier Tetrahedron 57 2001 8999 9010
22. A. Pardi, M. Billeter, and K. Wüthrich J. Mol. Biol. 180 1984 741 751
23. 50 determinable.
24. 2 substituent in Scheme 3. The correspondence with R and S descriptors is given for each compound in Table 1.
25. D.J. Abraham, R.D. Rosenstein, R.L. Lyon, and H.H.S. Fong Tetrahedron Lett. 13 1972 909 912
26. Though compound 5o was found inactive on KB cell lines in Ref. 5a), its cytotoxicity was found reproducibly 1/2 that of rhazinilam in the present assays.
27. 13C NMR attributions were again determined carefully.
28. H.H.A. Linde Helv. Chim. Acta 48 1965 1822 1842
29. Enraf-Nonius, Kappa-CCD Software, Enraf-Nonius, Delft, The Netherlands, 1997-2000.
30. G.M. Sheldrick Acta Crystallogr. A46 1990 467 473
31. Sheldrick G. M. SHELXL-93. Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1993.
32. C. Tempête, G.H. Werner, F. Favre, A. Rojas, and N. Langlois Eur. J. Med. Chem. 30 1995 647 650