Novel B-ring modified allocolchicinoids of the NCME series: Design, synthesis, antimicrotubule activity and cytotoxicity

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 7, 2003, Pages 1269-1281

  Bergemann, Silke ^c   Brecht, René ^a   Büttner, Frank ^a   Guénard, Daniel ^b   Gust, Ronald ^c   Seitz, Gunther ^a   Stubbs, Milton T ^a   Thoret, Sylviane ^b  

^a Pharmazeutisch Chemisches Inst P   (Germany)

^b CNRS   (France)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOCOLCHICINOID; ANTIMITOTIC AGENT; AZOCINE DERIVATIVE; COLCHICINE DERIVATIVE; ETHER DERIVATIVE; KETONE; LEAD; N ACETYLCOLCHINOL O METHYL ETHER; OXIME; SILANE DERIVATIVE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BECKMANN REARRANGEMENT; BREAST CARCINOMA; CANCER CELL; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CORRELATION ANALYSIS; CYTOTOXICITY; DRUG POTENCY; HUMAN; HUMAN CELL; IN VITRO STUDY; MICROTUBULE ASSEMBLY;

MINK CELL FOCUS-FORMING VIRUS;

EID: 0037375724     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00639-9     Document Type: Article

References (42)

1. Brecht R., Seitz G., Guénard D., Thoret S. Bioorg. Med. Chem. 8:2000;557.
2. Capraro, H.-G.; Brossi, A. In The Alkaloids; Brossi, A., Ed.; Academic: New York, 1984; Vol. 23, p 1, and references therein.
3. Boyé, O.; Brossi, A. In The Alkaloids; Brossi, A.; Cordell, G.A., Eds.; Academic: New York, 1992; Vol. 41, p 125.
4. Brossi A. J. Med. Chem. 33:1990;2311.
5. Banwell M.G. Pure Appl. Chem. 68:1996;539.
6. Hastie S.B. Pharm. Ther. 51:1991;377.
7. Shi Q., Chen K., Morris-Natschke S.L., Lee K.-H. Curr. Pharm. Des. 4:1998;219.
8. Brecht R., Haenel F., Seitz G. Liebigs Ann./Recueil. 1997;2275. and references cited therein.
9. Kang G.-J., Getahun Z., Muzaffar A., Brossi A., Hamel E. J. Biol. Chem. 265:1990;10255.
10. Bringmann G., Walter R., Weirich R. Angew. Chem., Int. Ed. Engl. 29:1990;977.
11. Brossi A., Boyé O., Muzaffar A., Yeh H.J.C., Toome V., Wegrzynski B., George C. FEBS. Lett. 262:1990;5.
12. Janik M.E., Bane S.L. Bioorg. Med. Chem. 10:2002;1895. and references cited therein.
13. Tomioka K., Kubota Y., Kawasaki H., Koga K. Tetrahedron Lett. 30:1989;2949.
14. Berg U., Bladh H., Svensson C., Wallin M. Bioorg. Med. Chem. Lett. 7:1997;2771.
15. Brecht, R. Dissertation, Marburg, April 1999.
16. Guan J., Zhu X.-K., Brossi A., Tachibana Y., Bastow K.F., Verdier-Pinard P., Hamel E., McPhail A.T., Lee K.-H. Collect. Czech. Chem. Commun. 64:1999;217.
17. Rapoport H., Williams A.R., Cisney M.E. J. Am. Chem. Soc. 73:1951;1414.
18. Kisfaludy L., Mohacsi T., Low M., Drexler F. J. Org. Chem. 44:1979;654.
19. Imming P., Jung M.-H. Arch. Pharm. Med. Chem. 328:1995;87.
20. Mphahlele M.J. J. Chem. Soc., Perkin Trans. 1. 1999;3477.
21. Shi Q., Chen K., Brossi A., Verdier-Pinard P., Hamal E., McPhail A.T., Lee K.-H. Helv. Chim. Acta. 81:1998;1023.
22. Bredereck H., Effenberger F., Simchen G. Angew. Chem., Int. Ed. Engl. 1:1962;331.
23. Wasserman H.H., Ives J.L. J. Org. Chem. 50:1985;3573. and references cited therein.
24. Bach N.J., Kornfeld E.C., Jones N.D., Chaney M.O., Dorman D.E., Paschal J.W., Clemens J.A., Smalstig E.B. J. Med. Chem. 23:1980;481.
25. Hesse, M.; Meier, H.; Zeeh, B. In Spektroskopische Methoden in der organischen Chemie; Georg Thieme: Stuttgart, 1991; Chapter 3, p 183.
26. Marinko P., Obreza A., Peterlin-Masic L., Krbavcic A., Kikelj D. J. Heterocyclic Chem. 37:2000;405.
27. Shelanski M.L., Gaskin F., Cantor C.R. Proc. Natl. Acad. Sci. U.S.A. 70:1973;765.
28. Zavala F., Guénard D. J. Med. Chem. 23:1980;546.
29. Boyé O., Itoh Y., Brossi A. Helv. Chim. Acta. 72:1989;1690.
30. Bernhardt G., Reile H., Birnböck H., Spruβ T., Schönenberger H. J. Cancer Res. Clin. Oncol. 118:1992;35.
31. SAPI 91: Hai-Fu, F. In Structure Analysis Programs with Intelligent Control; Rigaku Corporation: Tokyo, Japan, 1991.
32. DIRDIF94: Beurskens P.T., Admiraal G., Beurskens G., Bosman W.P., de Gelder R., Israel R., Smits J.M.M. The DIRDIF-94 Program System; Technical Report of the Crystallography Laboratory. 1994;University of Nijmegen, The Netherlands.
33. Cromer D.T., Waber J.T. International Tables for X-ray Crystallography. Kynoch. 1974;Birmingham, UK. Vol. IV, Table 2.2A.
34. Ibers J.A., Hamilton W.C. Acta Crystallogr. 17:1964;781.
35. Creagh D.C., McAuley W.J. International Tables for Crystallography. Kluwer Academic. 1992;Boston, MA. Vol. C, Table 4.2.6.8, p 219.
36. Creagh D.C., Hubbell J.H. International Tables for Crystallography. 1992;Kluwer Academic, Boston, MA. Vol. C Table 4.2.4.3, p 200.
37. teXsan: Crystal Structure Analysis Package; Molecular Structure Corp., 1985, 1992.
38. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications nos. CCDC 191524 for compound 8, 191525 for compound 11a and 191526 for compound 13. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336033, e-mail: deposit@ccdc.cam.ac.uk ).
39. SIR92: Altomare A., Cascarano M., Giacovazzo C., Guagliardi A. J. Appl. Cryst. 26:1993;343.
40. Hay R. J. Anal. Biochem. 171:1998;225.
41. Reile H., Birnböck H., Bernhardt G., Spruβ T., Schönenberger H. Anal. Biochem. 187:1990;262.
42. Gulotti M., Pasini A., Ugo R., Philipeschi St., Marmonti L., Spreafico F. Inorg. Chim. Acta. 91:1984;223.