Discovery of 3-aryl-5-aryl-1,2,4-oxadiazoles as a new series of apoptosis inducers. 2. Identification of more aqueous soluble analogs as potential anticancer agents

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 15, 2009, Pages 4410-4415

  Kemnitzer, William ^a   Kuemmerle, Jared ^a   Zhang, Han Zhong ^a   Kasibhatla, Shailaja ^a   Tseng, Ben ^a   Drewe, John ^a   Cai, Sui Xiong ^a  

^a Epicept Corporation Inc   (United States)

Author keywords

Anticancer agents; Apoptosis inducers; HTS; SAR

Indexed keywords

1,2,4 OXADIAZOLE DERIVATIVE; CASPASE 3; FURAN; GAMBOGIC ACID;

ANIMAL EXPERIMENT; APOPTOSIS; AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG SOLUBILITY; DRUG STRUCTURE; ENZYME ACTIVATION; GROWTH INHIBITION; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CHEMISTRY, PHARMACEUTICAL; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; HUMANS; INFUSIONS, INTRAVENOUS; MICE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NEOPLASM TRANSPLANTATION; OXADIAZOLES; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

ANIMALIA;

EID: 67649999910     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.05.052     Document Type: Article

References (39)

1. Varmus H. Science 312 (2006) 1162
2. Harrison M.R., Holen K.D., and Liu G. Clin. Adv. Hematol. Oncol. 7 (2009) 54
3. Kingston D.G., and Newman D.J. Curr. Opin. Drug Discovery Dev. 10 (2007) 130
4. Hunt J.T. Mol. Cancer Ther. 8 (2009) 275
5. Baselga J. Science 312 (2006) 1175
6. Cross S.A., and Lyseng-Williamson K.A. Drugs 67 (2007) 2645
7. Wood L.S., and Manchen B. Clin. J. Oncol. Nurs. 11 (2007) 649
8. Vial J.P., Belloc F., Dumain P., Besnard S., Lacombe F., Boisseau M.R., Reiffers J., and Bernard P. Leukocyte Res. 21 (1997) 163
9. Fesik S.W. Nat. Rev. Cancer 5 (2005) 876
10. 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
11. 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
12. 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 B.R., 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
13. Tolomeo M., and Simoni D. Curr. Med. Chem. Anticancer Agents 2 (2002) 387
14. Cai S.X., Zhang H.Z., Guastella J., Drewe J., Yang W., and Weber E. Bioorg. Med. Chem. Lett. 11 (2001) 39
15. Zhang H.Z., Kasibhatla S., Guastella J., Drewe J., Tseng B., and Cai S.X. Bioconjugate Chem. 14 (2003) 458
16. Cai S.X., Drewe J., and Kasibhatla S. Curr. Med. Chem. 13 (2006) 2627
17. Cai S.X., Nguyen B., Jia S., Guastella J., Reddy S., Tseng B., Drewe J., and Kasibhatla S. J. Med. Chem. 46 (2003) 2474
18. 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
19. 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
20. Kemnitzer W., Drewe J., Jiang S., Zhang H., Zhao J., Crogan-Grundy C., Xu L., Lamothe S., Gourdeau H., Denis R., Tseng B., Kasibhatla S., and Cai S.X. J. Med. Chem. 50 (2007) 2858
21. 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
22. 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
23. 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
24. 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
25. Sirisoma N., Pervin A., Nguyen B., Kasibhatla S., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. Lett. 19 (2009) 2305
26. Jiang S., Crogan-Grundy C., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. Lett. 18 (2008) 5725
27. Kasibhatla S., Baichwal V., Cai S.X., Roth B., Skvortsova I., Skvortsov S., Lukas P., English N.M., Sirisoma N., Drewe J., Pervin A., Tseng B., Carlson R.O., and Pleiman C.M. Cancer Res. 67 (2007) 5865
28. 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
29. 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
30. Zhang H.-Z., Claassen G., Crogan-Grundy C., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. 16 (2008) 222
31. 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
32. 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
33. 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
34. 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
35. Bernasek E. J. Org. Chem. 22 (1957) 1263
36. Chiou S., and Shine H.J. J. Heterocycl. Chem. 26 (1989) 125
37. Haugwitz R.D., Martinez A.J., Venslavsky J., Angel R.G., Maurer B.V., Jacobs G.A., Narayanan V.L., Cruthers L.R., and Szanto J. J. Med. Chem. 28 (1985) 1234
38. Pettit G.R., Temple Jr. C., Narayanan V.L., Varma R., Simpson M.J., Boyd M.R., Rener G.A., and Bansal N. Anticancer Drug Des. 10 (1995) 299
39. Pettit G.R., and Lippert III J.W. Anticancer Drug Des. 15 (2000) 203