Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 15, 2007, Pages 5122-5136

  Kaufmann, Doris ^a   Pojarová, Michaela ^a   Vogel, Susanne ^a   Liebl, Renate ^a   Gastpar, Robert ^a   Gross, Dietmar ^a   Nishino, Tsuyuki ^a   Pfaller, Tobias ^a   von Angerer, Erwin ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Breast cancer; Cell cycle arrest; Phenylindoles; Tubulin polymerization

Indexed keywords

2 (3 HYDROXY 4 METHOXYPHENYL) 6 METHOXYINDOLE 3 CARBALDEHYDE; 2 (3,4 DIMETHOXYPHENYL) 6 METHOXYINDOLE 3 CARBALDEHYDE; 2 (4 BUTYLPHENYL) 5 ETHYLINDOLE 3 CARBALDEHYDE; 2 (4 METHOXYPHENYL) 5 METHYLINDOLE 3 CARBALDEHYDE; 2 (4 METHOXYPHENYL) 5 PENTYLINDOLE 3 CARBALDEHYDE; 2 (4 METHOXYPHENYL) 5 PROPYLINDOLE 3 CARBALDEHYDE; 5 BUTYL 2 (4 ETHYLPHENYL)INDOLE 3 CARBALDEHYDE; 5 BUTYL 2 (4 FLUOROPHENYL)INDOLE 3 CARBALDEHYDE; 5 BUTYL 2 (4 METHOXYPHENYL 3 [(METHYLIMINO)METHYL]INDOLE; 5 BUTYL 2 (4 METHOXYPHENYL)INDOLE 3 CARBALDEHYDE; 5 BUTYL 2 (4 METHYLPHENYL)INDOLE 3 CARBALDEHYDE; 5 BUTYL 2 [4 (TRIFLUOROMETHYL)PHENYL] 3 [(METHYLIMINO)METHYL]INDOLE; 5 BUTYL 2 [4 (TRIFLUOROMETHYL)PHENYL]INDOLE 3 CARBALDEHYDE; 5 BUTYL 3 [(HYDROXYIMINO)METHYL] 2 (4 METHOXYPHENYL)INDOLE; 5 BUTYL 3 [(HYDROXYIMINO)METHYL] 2 [4 (TRIFLUOROMETHYL)PHENYL]INDOLE; 5 FLUORO 2 (4 METHOXYPHENYL)INDOLE 3 CARBALDEHYDE; 5 HEXYL 2 (4 METHOXYPHENYL)INDOLE 3 CARBALDEHYDE; 5 HEXYL 2 [4 (TRIFLUOROMETHYL)PHENYL]INDOLE 3 CABALDEHYDE; 5 ISOPROPYL 2 (4 METHOXYPHENYL)INDOLE 3 CARBALDEHYDE; 5 PENTYL 2 (4 METHOXYPHENYL) INDOL 3 [(METHYLIMINO)METHYL]INDOLE; 5 PENTYL 2 [4 (TRIFLUOROMETHYL)PHENYL]INDOLE 3 CABALDEHYDE; 5 SEC BUTYL 2 (4 METHOXYPHENYL)INDOLE 3 CARBALDEHYDE; 5 TERT BUTYL 2 (4 METHOXYPHENYL)INDOLE 3 CARBALDEHYDE; 6 CHLORO 2 (4 METHOXYPHENYL) 5 METHYLINDOLE 3 CARBALDEHYDE; 6 CHLORO 2 (4 METHOXYPHENYL)INDOLE 3 CARBALDEHYDE; 6 CHLORO 2 (4 METHYLPHENYL)INDOLE 3 CARBALDEHYDE; 6 METHOXY 2 (3 METHOXYPHENYL)INDOLE 3 CARBALDEHYDE; 6 METHOXY 2 (4 METHOXYPHENYL) 3 [(METHYLIMINO)METHYL]INDOLE; 6 METHOXY 2 (4 METHYLPHENYL)INDOLE 3 CARBALDEHYDE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CANCER INHIBITION; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IC 50; LIPOPHILICITY; MICROTUBULE ASSEMBLY; NONHUMAN;

ALDEHYDES; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SHAPE; CELLS; HUMANS; MITOSIS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS; TUBULIN;

EID: 34249944413     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.05.030     Document Type: Article

References (23)

1. von Angerer E. Curr. Opin. Drug Discovery Dev. 3 (2000) 575-584
2. Tron G.C., Pirali T., Sorba G., Pagliai F., Busacca S., and Genazzani A.A. J. Med. Chem. 49 (2006) 3033-3044
3. von Angerer E. Exp. Opin. Ther. Patents 9 (1999) 1069-1081
4. Prinz H., Ishii Y., Hirano T., Stoiber T., Camacho Gomez J.A., Schmidt P., Dussmann H., Burger A.M., Prehn J.H., Gunther E.G., Unger E., and Umezawa K. J. Med. Chem. 46 (2003) 3382-3394
5. Liou J.P., Chang J.Y., Chang C.W., Chang C.Y., Mahindroo N., Kuo F.M., and Hsieh H.P. J. Med. Chem. 47 (2004) 2897-2905
6. Romagnoli R., Baraldi P.G., Pavani M.G., Tabrizi M.A., Preti D., Fruttarolo F., Piccagli L., Jung M.K., Hamel E., Borgatti M., and Gambari R. J. Med. Chem. 49 (2006) 3906-3915
7. Brancale A., and Silvestri R. Med. Res. Rev. 27 (2007) 209-238
8. De Martino G., Edler M.C., La Regina G., Coluccia A., Barbera M.C., Barrow D., Nicholson R.I., Chiosis G., Brancale A., Hamel E., Artico M., and Silvestri R. J. Med. Chem. 49 (2006) 947-954
9. Dupeyre G., Chabot G.G., Thoret S., Cachet X., Seguin J., Guenard D., Tillequin F., Scherman D., Koch M., and Michel S. Bioorg. Med. Chem. 14 (2006) 4410-4426
10. Mahboobi S., Sellmer A., Eichhorn E., Beckers T., Fiebig H.H., and Kelter G. Eur. J. Med. Chem. 40 (2005) 85-92
11. Kuo C.C., Hsieh H.P., Pan W.Y., Chen C.P., Liou J.P., Lee S.J., Chang Y.L., Chen L.T., Chen C.T., and Chang J.Y. Cancer Res. 64 (2004) 4621-4628
12. Liou J.P., Chang Y.L., Kuo F.M., Chang C.W., Tseng H.Y., Wang C.C., Yang Y.N., Chang J.Y., Lee S.J., and Hsieh H.P. J. Med. Chem. 47 (2004) 4247-4257
13. Liou J.P., Mahindroo N., Chang C.W., Guo F.M., Lee S.W., Tan U.K., Yeh T.K., Kuo C.C., Chang Y.W., Lu P.H., Tung Y.S., Lin K.T., Chang J.Y., and Hsieh H.P. ChemMedChem 1 (2006) 1106-1118
14. Mahboobi S., Pongratz H., Hufsky H., Hockemeyer J., Frieser M., Lyssenko A., Paper D.H., Bürgermeister J., Böhmer F.D., Fiebig H.H., Burger A.M., Baasner S., and Beckers T. J. Med. Chem. 44 (2001) 4535-4553
15. Wang L., Woods K.W., Li Q., Barr K.J., McCroskey R.W., Hannick S.M., Gherke L., Credo R.B., Hui Y.H., Marsh K., Warner R., Lee J.Y., Zielinski-Mozng N., Frost D., Rosenberg S.H., and Sham H.L. J. Med. Chem. 45 (2002) 1697-1711
16. Pandit B., Sun Y., Chen P., Sackett D.L., Hu Z., Rich W., Li C., Lewis A., Schaefer K., and Li P.K. Bioorg. Med. Chem. 14 (2006) 6492-6501
17. Thorpe P.E. Clin. Cancer Res. 10 (2004) 415-427
18. Chaplin D.J., Horsman M.R., and Siemann D.W. Curr. Opin. Investig. Drugs 7 (2006) 522-528
19. Gastpar R., Goldbrunner M., Marko D., and von Angerer E. J. Med. Chem. 41 (1998) 4965-4972
20. Romagnoli R., Baraldi P.G., Remusat V., Carrion M.D., Cara C.L., Preti D., Fruttarolo F., Pavani M.G., Tabrizi M.A., Tolomeo M., Grimaudo S., Balzarini J., Jordan M.A., and Hamel E. J. Med. Chem. 49 (2006) 6425-6428
21. Watanabe J., Natsume T., Fujio N., Miyasaka K., and Kobayashi M. Apoptosis 5 (2000) 345-353
22. De Martino G., La Regina G., Coluccia A., Edler M.C., Barbera M.C., Brancale A., Wilcox E., Hamel E., Artico M., and Silvestri R. J. Med. Chem. 47 (2004) 6120-6123
23. Flynn B.L., Hamel E., and Jung M.K. J. Med. Chem. 45 (2002) 2670-2673