Discovery of N-aryl-9-oxo-9H-fluorene-1-carboxamides as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 2. Structure-activity relationships of the 9-oxo-9H-fluorene ring

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 3, 2010, Pages 1288-1292

  Kemnitzer, William ^a   Sirisoma, Nilantha ^a   Jiang, Songchun ^a   Kasibhatla, Shailaja ^a   Crogan Grundy, Candace ^a   Tseng, Ben ^a   Drewe, John ^a   Cai, Sui Xiong ^a  

^a EpiCept Corporation   (United States)

Author keywords

Anticancer agents; Apoptosis inducers; SAR; Tubulin inhibition

Indexed keywords

AMIDE; ANTINEOPLASTIC AGENT; CASPASE; DIBENZOTHIOPHENE DERIVATIVE; FLUORENE DERIVATIVE; PACLITAXEL; TUBULIN; VINBLASTINE; FLUORENE; FLUORENE-1-CARBOXYLIC ACID;

APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CANCER INHIBITION; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; COLON CANCER; DRUG MECHANISM; FEMALE; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; INHIBITION KINETICS; LIVER CELL CARCINOMA; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; CHEMISTRY; COMPARATIVE STUDY; DRUG DEVELOPMENT; DRUG EFFECTS; HCT116 CELL LINE; PHYSIOLOGY; PROCEDURES;

AMIDES; ANTINEOPLASTIC AGENTS; APOPTOSIS; CASPASES; DRUG DISCOVERY; FLUORENES; HCT116 CELLS; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 74049105599     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.11.025     Document Type: Article

References (31)

1. Henson P.M., Bratton D.L., and Fadok V.A. Curr. Biol. 11 (2001) R795
2. Reed J.C. Nat. Rev. Drug Disc. 1 (2002) 111
3. Salvesen G.S. Essays Biochem. 38 (2002) 9
4. Vial J.P., Belloc F., Dumain P., Besnard S., Lacombe F., Boisseau M.R., Reiffers J., and Bernard P. Leuk. Res. 21 (1997) 163
5. Fesik S.W. Nat. Rev. Cancer. 5 (2005) 876
6. van Delft M.F., Wei A.H., Mason K.D., Vandenberg C.J., Chen L., Czabotar P.E., Willis S.N., Scott C.L., Day C.L., Cory S., Adams J.M., Roberts A.W., and Huang D.C. Cancer Cell 10 (2006) 389
7. Zobel K., Wang L., Varfolomeev E., Franklin M.C., Elliott L.O., Wallweber H.J., Okawa D.C., Flygare J.A., Vucic D., Fairbrother W.J., and Deshayes K. ACS Chem. Biol. 1 (2006) 525
8. Shangary S., Qin D., McEachern D., Liu M., Miller R.S., Qiu S., Nikolovska-Coleska Z., Ding K., Wang G., Chen J., Bernard D., Zhang J., Lu Y., Gu Q., Shah R.B., Pienta K.J., Ling X., Kang S., Guo M., Sun Y., Yang D., and Wang S. Proc. Natl. Acad. Sci. U.S.A. 105 (2008) 3933
9. Cai S.X., Zhang H.-Z., Guastella J., Drewe J., Yang W., and Weber E. Bioorg. Med. Chem. Lett. 11 (2001) 39
10. Cai S.X., Drewe J., and Kasibhatla S. Curr. Med. Chem. 13 (2006) 2627
11. Cai S.X., Nguyen B., Jia S., Guastella J., Reddy S., Tseng B., Drewe J., and Kasibhatla S. J. Med. Chem. 46 (2003) 2474
12. Zhang H.Z., Kasibhatla S., Wang Y., Herich J., Guastella J., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. 12 (2004) 309
13. Kasibhatla S., Jessen K., Maliartchouk S., Wang J., English N., Drewe J., Qui L., Archer S., Ponce A., Sirisoma N., Jiang S., Zhang H.-Z., Gehlsen K., Cai S.X., Green D.R., and Tseng B. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 12095
14. Kemnitzer W., Kasibhatla S., Jiang S., Zhang H., Wang Y., Zhao J., Jia S., Herich J., Labreque D., Storer R., Meerovitch K., Bouffard D., Rej R., Denis R., Blais C., Lamothe S., Attardo G., Gourdeau H., Tseng B., Drewe J., and Cai S. X. J. Med. Chem. 47 (2004) 6299
15. Gourdeau H., Leblond L., Hamelin B., Desputeau C., Dong K., Kianicka I., Custeau D., Bourdeau C., Geerts L., Cai S.X., Drewe J., Labrecque D., Kasibhatla S., and Tseng B. Mol. Cancer Ther. 3 (2004) 1375
16. Kemnitzer W., Drewe J., Jiang S., Zhang H., Crogan-Grundy C., Labreque D., Bubenick M., Attardo G., Denis R., Lamothe S., Gourdeau H., Tseng B., Kasibhatla S., and Cai S.X. J. Med. Chem. 51 (2008) 417
17. Zhang H.-Z., Kasibhatla S., Kuemmerle J., Kemnitzer W., Oliis-Mason K., Qui L., Crogran-Grundy C., Tseng B., Drewe J., and Cai S.X. J. Med. Chem. 48 (2005) 5215
18. Jessen K., English N., Wang J., Qui L., Brand R., Maliartchouk S., Drewe J., Kuemmerle J., Zhang H.-Z., Gehlsen K., Tseng B., Cai S.X., and Kasibhatla S. Mol. Cancer Ther. 4 (2005) 761
19. Sirisoma N., Kasibhatla S., Nguyen B., Pervin A., Wang Y., Claassen G., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. 14 (2006) 7761
20. Sirisoma N., Pervin A., Nguyen B., Kasibhatla S., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. Lett. 19 (2009) 2305
21. Sirisoma N., Kasibhatla S., Pervin A., Zhang H., Jiang S., Willardsen J.A., Anderson M., Baichwal V., Mather G.G., Jessing K., Hussain R., Hoang K., Pleiman C.M., Tseng B., Drewe J., and Cai S.X. J. Med. Chem. 51 (2008) 4771
22. Sirisoma N., Pervin A., Zhang H., Jiang S., Willardsen A.J., Anderson M., Mather G.G., Pleiman C.M., Kasibhatla S., Tseng B., Drewe J., and Cai S.X. J. Med. Chem. 52 (2009) 2341
23. Zhang H.-Z., Claassen G., Crogan-Grundy C., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. 16 (2008) 222
24. Jiang S., Crogan-Grundy C., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. Lett. 18 (2008) 5725
25. Kemnitzer W., Kuemmerle J., Jiang S., Zhang H., Sirisoma N., Kasibhatla S., Crogan-Grundy C., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. Lett. 18 (2008) 6259
26. Kemnitzer W., Sirisoma N., Nguyen B., Jiang S., Kasibhatla S., Crogan-Grundy C., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. Lett. 19 (2009) 3045
27. Tye H., Eldred C., and Wills M. Synlett 7 (1995) 770
28. Garascia R.J., and Overberg R.J. J. Org. Chem. 19 (1954) 27
29. Garascia R.J., Fries E.F., and Ching C. J. Org. Chem. 17 (1952) 226
30. Barron D.M., Chatterjee S.K., Ravindra R., Roof R., Baloglu E., Kingston D.G.I., and Bane S. Anal. Biochem. 315 (2003) 49
31. Ester K., Hranjec M., Piantanida I., Caleta I., Jarak I., Pavelić K., Kralj M., and Karminski-Zamola G. J. Med. Chem. 52 (2009) 2482