Hit to Lead optimization of a novel class of squarate-containing polo-like kinases inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 24, 2012, Pages 7615-7622

  Zhang, Qingwei ^a   Xia, Zhiren ^a   Mitten, Michael J ^a   Lasko, Loren M ^a   Klinghofer, Vered ^a   Bouska, Jennifer ^a   Johnson, Eric F ^a   Penning, Thomas D ^a   Luo, Yan ^a   Giranda, Vincent L ^a   Shoemaker, Alexander R ^a   Stewart, Kent D ^a   Djuric, Stevan W ^a   Vasudevan, Anil ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Antitumor; Hit to Lead; Kinases; Plk

Indexed keywords

ANTINEOPLASTIC AGENT; AROMATIC AMINE; BI 2356; GEMCITABINE; POLO LIKE KINASE INHIBITOR; SQUARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG HALF LIFE; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SAFETY; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; HYDROPHOBICITY; IC 50; MOLECULAR MODEL; MOUSE; NONHUMAN; REACTION OPTIMIZATION; STRUCTURE ACTIVITY RELATION; TUMOR MODEL; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL CYCLE PROTEINS; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NEOPLASMS, EXPERIMENTAL; PROTEIN KINASE INHIBITORS; PROTEIN-SERINE-THREONINE KINASES; PROTO-ONCOGENE PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84870254117     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.10.009     Document Type: Article

References (31)

1. D.M. Glover, I.M. Hagan, Tavares, and A.M. Álvaro Genes Dev. 12 1998 3777
2. M.M. Donaldson, A.A. Tavares, I.M. Hagan, E.A. Nigg, and D.M.J. Glover Cell. Sci. 114 2001 2357
3. X. Liu, and R.L. Erikson Proc. Natl. Acad. Sci. U.S.A. 99 2002 8672
4. X. Liu, and R.L. Erikson Proc. Natl. Acad. Sci. U.S.A. 100 2003 5789
5. B. Spankuch-Schmitt, G. Wolf, C. Solbach, S. Loibl, R. Knecht, M. Stegmuller, G. von Minckwitz, M. Kaufmann, and K. Strebhardt Oncogene 21 2002 3162
6. N. Takai, R. Hamanaka, J. Yoshimatsu, and I. Miyakawa Oncogene 24 2005 287
7. S.L. Warner, B.J. Stephens, and D.D. Von Hoff Curr. Oncol. Rep. 10 2008 122
8. A. Jalili, A. Moser, M. Pashenkov, C. Wagner, G. Pathria, V. Borgdorff, M. Gschaider, G. Stingl, S. Ramaswamy, and S.N.J. Wagner Invest. Dermatol. 2011 1886 131
9. M. Steegmaier, M. Hoffmann, A. Baum, P. Lenart, M. Petronczki, M. Krssak, U. Guertler, P. Garin-Chesa, S. Lieb, J. Quant, M. Grauert, G.R. Adolf, N. Kraut, J. Peters, and W. Rettig Curr. Biol. 17 2007 316
10. R. Hofheinz, S. Al-Batran, A. Hochhaus, E. Jaeger, V.L. Reichardt, H. Fritsch, D. Trommeshauser, and G. Munzert Clin. Cancer Res. 16 2010 4666
11. D. Rudolph, M. Steegmaier, M. Hoffmann, M. Grauert, A. Baum, J. Quant, C. Haslinger, P. Garin-Chesa, and G.R. Adolf Clin. Cancer Res. 15 2009 3094
12. N. Grinshtein, A. Datti, M. Fujitani, D. Uehling, M. Prakesch, M. Isaac, M. Irwin, J. Wrana, R. Al-Awar, and D. Kaplan Cancer Res. 71 2011 1385
13. P. Schoeffski, J. Blay, J. De Greve, E. Brain, J. Machiels, J. Soria, S. Sleijfer, P. Wolter, I. Ray-Coquard, C. Fontaine, G. Munzert, H. Fritsch, G. Hanft, C. Aerts, J. Rapion, A. Allgeier, J. Bogaerts, and D. Lacombe Eur. J. Cancer 46 2010 2206
14. P. Schoffski Oncologist 14 2009 559
15. D.R. Taft, R. Dave, A.M. Gillum, and M. Maniar Drugs Future 36 2011 433
16. M.V.R. Reddy, P. Venkatapuram, M.R. Mallireddigari, V.R. Pallela, S.C. Cosenza, K.A. Robell, B. Akula, B.S. Hoffman, and E.P.J. Reddy Med. Chem. 54 2011 6254
17. P. Traxler, and P. Furet Pharmacol. Ther. 82 1999 195
18. Davis-Ward, R.; Mook, R. A., Jr.; Neeb, M. J.; Salovich, J. M. WO2004074244.
19. Munzert, G.; Steegmaier, M. WO2006018185.
20. Munzert, G.; Steegmaier, M.; Baum, A. WO2006018182.
21. K. Strebhardt, and A. Ullrich Nat. Rev. Cancer 6 2006 321
22. E.J. Perola Med. Chem. 53 2010 2986
23. P.D. Leeson, and A.M.J. Davis Med. Chem. 47 2004 6338
24. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv. Drug Deliv. Rev. 46 2001 3
25. Y.C.J. Martin Med. Chem. 48 2005 3164
26. van de Waterbeemd, Han; Smith, Dennis A.; Beaumont, Kevin; Walker, Don K. J. Med. Chem. 2001, 44, 1313.
27. P.D. Leeson, and B. Springthorpe Nat. Rev. Drug Discov. 6 2007 881
28. B.G. Szczepankiewicz, C. Kosogof, L.T.J. Nelson, G. Liu, B. Liu, H. Zhao, M.D. Serby, Z. Xin, M. Liu, R.J. Gum, D.L. Haasch, S. Wang, E.J. Johnson, T.H. Lubben, M.A. Stashko, E.T. Olejniczak, C. Sun, S.A. Dorwin, K. Haskins, C. Abad-Zapatero, E.H. Fry, C.W. Hutchins, C. Rondinone, and J.M.J. Trevillyan Med. Chem. 49 2006 3563
29. P.J. Manley, A.E. Balitza, M.T. Bilodeau, K.E. Coll, G.D. Hartman, R.C. McFall, K.W. Rickert, L.D. Rodman, and K.A. Thomas Bioorg. Med. Chem. Lett. 13 2003 1673
30. J. Spychala Synth. Commun. 1997 1943 27
31. H.Q. Zhang, Z. Xia, A. Vasudevan, and S.W. Djuric Tetrahedron Lett. 47 2006 4881