Lead optimization of novel p53-MDM2 interaction inhibitors possessing dihydroimidazothiazole scaffold

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 3, 2013, Pages 728-732

  Miyazaki, Masaki ^a   Naito, Hiroyuki ^a   Sugimoto, Yuuichi ^a   Kawato, Haruko ^a   Okayama, Tooru ^a   Shimizu, Hironari ^a   Miyazaki, Masaya ^a   Kitagawa, Mayumi ^a   Seki, Takahiko ^a   Fukutake, Setsuko ^a   Aonuma, Masashi ^a   Soga, Tsunehiko ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

Dihydroimidazothiazole; MDM2; p53; Protein protein interaction inhibitor

Indexed keywords

AMIDE; DIHYDROIMIDAZOTHIAZOLE; METHYL GROUP; NUTLIN 3; PROLINE; PROTEIN MDM2; PROTEIN P53; PYRROLIDINE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; PROTEIN PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION;

HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IMIDAZOLES; INHIBITORY CONCENTRATION 50; PROTEIN BINDING; PROTO-ONCOGENE PROTEINS C-MDM2; STEREOISOMERISM; THIAZOLES; TUMOR SUPPRESSOR PROTEIN P53;

EID: 84872351571     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.11.091     Document Type: Article

References (19)

1. J. Momand, G.P. Zambetti, D.C. Olson, D. George, and A.J. Levine Cell 69 1992 1237
2. Y. Haupt, R. Maya, A. Kazaz, and M. Oren Nature 387 1997 296
3. M.H.G. Kubbutat, S.N. Jones, and K.H. Vousden Nature 387 1997 299
4. T. Iwakuma, and G. Lozano Mol. Cancer Res. 1 2003 993
5. M. Hollstein, K. Rice, M.S. Greenblatt, T. Soussi, R. Fuchs, T. Sørlie, E. Hovig, B. Smith-Sørensen, R. Montesano, and C.C. Harris Nucleic Acids Res. 22 1994 3551
6. M. Olivier, M. Hollstein, and P. Hainaut Cold Spring Harbor Perspect. Biol. 2 2010 a001008
7. I. Massova, and P.A. Kollman J. Am. Chem. Soc. 121 1999 8133
8. P.H. Kussie, S. Gorina, V. Marechal, B. Elenbaas, J. Moreau, A.J. Levine, and N.P. Pavletich Science 274 1996 948
9. L.M. Espinoza-Fonseca, and J.G. Trujillo-Ferrara Biopolymers 83 2006 365
10. L.T. Vassilev, B.T. Vu, B. Graves, D. Carvajal, F. Podlaski, Z. Filipovic, N. Kong, U. Kammlott, C. Lukacs, C. Klein, N. Fotouhi, and E.A. Liu Science 303 2004 844
11. J.G. Allen, M.P. Bourbeau, G.E. Wohlhieter, M.D. Bartberger, K. Michelsen, R. Hungate, R.C. Gadwood, R.D. Gatson, B. Evans, L.W. Mann, M.E. Matison, S. Schneider, X. Huang, D. Yu, P.S. Andrews, A. Reichelt, A.M. Long, P. Yakowec, E.Y. Yang, T.A. Lee, and J.D. Oliner J. Med. Chem. 52 2009 7044
12. P. Furet, P. Chène, A.D. Pover, T.S. Valat, J.H. Lisztwan, J. Kallen, and K. Masuya Bioorg. Med. Chem. Lett. 22 2012 3498
13. Y. Rew, D. Sun, F.G.-L.D. Turiso, M.D. Bartberger, H.P. Beck, J. Canon, A. Chen, D. Chow, J. Deignan, B.M. Fox, D. Gustin, X. Huang, M. Jiang, X. Jiao, L. Jin, F. Kayser, D.J. Kopecky, Y. Li, M.-C. Lo, A.M. Long, K. Michelsen, J.D. Oliner, T. Osgood, M. Ragains, A.Y. Saiki, S. Schneider, M. Toteva, P. Yakowec, X. Yan, Q. Ye, D. Yu, X. Zhao, J. Zhou, J.C. Medina, and S.H. Olson J. Med. Chem. 55 2012 4936
14. M. Miyazaki, H. Kawato, H. Naito, M. Ikeda, M. Miyazaki, M. Kitagawa, T. Seki, S. Fukutake, M. Aonuma, and T. Soga Bioorg. Med. Chem. Lett. 22 2012 6338
15. Unpublished results.
16. S.V. Pansare, A.N. Rai, and S.N. Kate Synlett 1998 623
17. F. Couty, G. Evano, M. Vargas-Sanchez, and G. Bouzas J. Org. Chem. 70 2005 9028
18. Uoto, K.; Takeda, Y.; Sakamoto, A.; Takayanagi, Y. Patent WO2007/049575, 2007.
19. Kawato, H.; Miyazaki, M.; Sugimoto, Y.; Naito, H.; Okayama, T.; Soga, T.; Uoto, K. Patent WO2008/072655, 2008.