Solution-phase parallel synthesis of Hsp90 inhibitors

Journal of Combinatorial Chemistry

Volumn 11, Issue 5, 2009, Pages 860-874

  Cho Schultz, Sujin ^a   Patten, Monica Jo ^a   Huang, Buwen ^a   Elleraas, Jeff ^a   Gajiwala, Ketan S ^a   Hickey, Michael J ^a   Wang, Jeff ^a   Mehta, Pramod P ^a   Kang, Ping ^a   Gehring, Michael R ^a   Kung, Pei Pei ^a   Sutton, Scott C ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCURONIDE; HEAT SHOCK PROTEIN 90;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; GEL CHROMATOGRAPHY; HUMAN; HYDROGEN BOND; LIVER CELL; METABOLISM; METHODOLOGY; PHARMACOKINETICS; PROTEIN CONFORMATION; X RAY CRYSTALLOGRAPHY;

CHROMATOGRAPHY, GEL; COMBINATORIAL CHEMISTRY TECHNIQUES; CRYSTALLOGRAPHY, X-RAY; GLUCURONIDES; HEPATOCYTES; HSP90 HEAT-SHOCK PROTEINS; HUMANS; HYDROGEN BONDING; PHARMACOKINETICS; PROTEIN CONFORMATION;

EID: 70349322618     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc900056d     Document Type: Article

References (40)

1. Pearl, L. H.; Prodromou, C. Annu. Rev. Biochem. 2006, 75, 111.
2. Bagateli, R.; Whitesell, L. Mol. Cancer Ther. 2004, 3, 1021.
3. (a) Mohsin, S. K.; Weiss, H. L.; Gutierrez, M. C.; Chamness, G. C.; Schiff, R.; DiGiovanna, M. P.; Wang, G X.; Hilsenbeck, S. G.; Osborne, C. K.; Allred, D. C.; Elledge, R.; Chang, J. G J. Clin. Oncol. 2005, 23 (11), 2460.
4. (b) Stebbins, C. E.; Russo, A. A.; Schneider, C.; Rosen, N.; Haiti, F. U.; Pavletich, N. P. Cell 1997, 89 (2), 239.
5. (a) Janin, Y. L. J. Med. Chem. 2005, 48, 7503.
6. (b) Drysdale, M. J.; Brough, P. A.; Massey, A.; Jensen, M. R.; Schoepfer, J. Curr. Opin. Drug Discovery Dev. 2006, 9, 483.
7. (c) McDonald, E.; Workman, P.; Jones, K. Curr. Top. Med. Chem. 2006, 6, 1091.
8. (d) Messaoudi, S.; Peyrat, J. F.; Brion, J. D.; Alami, M. Anti-Cancer Agents Med. Chem. 2008, 8, 761.
9. (e) Taldone, T.; Gozman, A.; Maharaj, R.; Chiosis, G. Curr. Opin. Pharmacol. 2008, 8, 370.
10. (f) Drysdale, M. J.; Brough, P. A. Curr. Top. Med. Chem. 2008, 8, 859.
11. (g) Chiosis, G.; Lopes, E. C.; Solit, D. Curr. Opin. Invest. Drugs 2006, 7, 534.
12. Supko, J. G.; Hickman, R. L.; Grever, M. R.; Malspeis, L. Cancer Chemother. Pharmacol. 1995, 36, 305.
13. (a) Schnur, R. C.; Corman, M. L.; Gallaschun, R. J.; Cooper, B. A.; Dee, M. F.; Doty, J. L.; Muzzi, M. L.; Moyer, J. D.; DiOrio, C. I.; Barbacci, E. G.; Miller, P. E.; O'Brien, A. T.; Morin, M. J.; Foster, B. A.; Pollack, V. A.; Savage, D. M.; Sloan, D. E.; Pustilnik, L. R.; Moyer, M. P. J. Med. Chem. 1995, 38, 3806.
14. (b) Sausville, E. A.; Tomaszewski, J. E.; Ivy, P. Curr. Cancer Drug Targets 2003, 3, 311.
15. Tian, Z.; Liu, Y.; Zhang, D.; Wang, Z.; Dong, S. D.; Carreras, G W.; Zhou, Y.; Rastelli, G.; Santi, D. V.; Myles, D. G Bioorg. Med. Chem. 2004, 12, 5317.
16. Ge, J.; Normant, E.; Porter, J. R.; Ali, J. A.; Dembski, M. S.; Gao, Y.; Georges, A. T.; Grenier, L.; Pak, R. H.; Patterson, J.; Sydor, J. R.; Tibbitts, T. T.; Tong, J. K.; Adams, J.; Palombella, V. J. J. Med. Chem. 2006, 49, 4606.
17. (a) Kelland, L. R.; Sharp, S. Y.; Rogers, P. M.; Myers, T. G.; Workman, P. J. Natl. Cancer Inst. 1999, 91, 1940.
18. (b) Diakalov, S.; Landmesser, U.; Harrison, D. G. J. Biol. Chem. 2002, 277, 25480.
19. Geng, X.; Yang, Z.-Q.; Danishefsky, S. J. Synlett. 2004, 8, 1325.
20. (a) Brough, P. A.; Aherne, W.; Barril, X.; Borgognoni, J.; Boxall, K.; Cansfield, J. E.; Cheung, K.-M.; Collins, I.; Davies, N. G. M.; Drysdale, M. J.; Dymock, B.; Eccles, S. A.; Finch, H.; Fink, A.; Hayes, A.; Howes, R.; Hubbard, R. E.; James, K.; Jordan, A. M.; Lockie, A.; Martins, V.; Massey, A.; Matthews, T. P.; McDonald, E.; Northfield, G J.; Pearl, L. H.; Prodromou, C.; Ray, S.; Raynaud, F. L; Roughley, S. D.; Sharp, S. Y.; Surgenor, A.; Walmsley, D. L.; Webb, P.; Wood, M.; Workman, P.; Wright, L. J. Med. Chem. 2008, 51, 196.
21. (b) Dymock, B. W.; Barril, X.; Brough, P. A.; Cansfield, J. E.; Massey, A.; McDonald, E.; Hubbard, R. E.; Surgenor, A.; Roughley, S. D.; Webb, P.; Workman, P.; Wright, L.; Drysdale, M. J. J. Med. Chem. 2005, 48, 4212.
22. (a) Shen, G.; Wang, M.; Welch, T. R.; Blagg, B. S. J. J. Org. Chem. 2006, 71, 7618.
23. (b) Shen, G.; Blagg, B. S. J. Org. Lett. 2005, 7(11), 2157.
24. (a) Chessari, G.; Congreve, M. S.; Navarro, E. F.; Frederickson, M.; Murray, C.Woolford, A. J.; Carr, M. G.; Downham, R.; O'Brien, M. A.; Phillips, T. R.; Woodhead, A. J. Hydroxybenzamide Derivatives and Their Use as Inhibitors of Hsp90. Int. Pat. Appl. WO2006109085, April 13, 2006.
25. (b) Chessari, G.; Congreve, M. S.; Navarro, E. F.; Frederickson, M.; Murray, C.Woolford, A. J.; Carr, M. G.; O'Brien, M. A.; Woodhead, A. J. Pharmaceutical Compounds. Int. Pat. Appl. WO2006109075, April 13, 2006.
26. Kung, P.-P.; Funk, L.; Meng, J.; Collins, M.; Zhou, J. Z.; Johnson, M. J.; Ekker, A.; Wang, J.; Mehta, P.; Yin, M.J.; Rodgers, C.Davies, J. F.; Bayman, E.; Smeal, T.; Maegley, K. A.; Gehring, M. R. Bioorg. Med. Chem. Lett. 2008, 18, 6273.
27. Ouzzine, M.; Barre, L.; Netter, P.; Magdalou, J.; FournelGigleux, S. Drug Met. Rev. 2003, 35 (4), 287.
28. A single O-glucuronide adduct was observed by mass spectral analysis of 24 when subjected to a combination cocktail of human liver microsomes containing UDGPA and NADPH.
29. (a) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
30. (b) Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-yi. J. Am. Chem. Soc. 2006, 128, 3538.
31. (c) Klapars, A.; Campos, K. R.; Waldman, J. H.; Zewge, D.; Dormer, P. G.; Chen, C.-yi. J. Org. Chem. 2008, 73, 4986.
32. At the time this work was completed, Peter O'Brien and coworkers had not yet developed their sparteine surrogate bases for generation of either enantiomer during asymmetric deprotonation of N-Boc pyrrolidine.
33. Stead, D.; O'Brien, P.; Sanderson, A. Org. Lett. 2008, 10 (7), 1409.
34. Basu, A.; Thayumanavan, S. Angew. Chem., Int. Ed. 2002, 41, 716.
35. Removal of the 2-OH group results in a 190-fold loss in binding potency while removal of the 4-OH group results in a 300-fold loss in binding potency as shown by the pairwise comparison below.
36. Lima, L. M.; Barreiro, E. Curr. Med. Chem. 2005, 12, 23.
37. Ventura, M.; Farrell, W.; Aurigemma, C.; Tivel, K.; Greig, M.; Wheatley, J.; Yanovsky, A.; Milgram, K. E.; Dalesandro, D.; DeGuzman, R.; Tran, P.; Nguyen, L.; Chung, L.; Gron, O.; Koch, G A. J. Chromatogr., A 2004, 1036 (1), 7-13.
38. Camp, D.; Matthews, C. F.; Neville, S. T.; Rouns, M.; Scott, R. W.; Truong, Y. Org. Process Res. Dev. 2006,10 (4), 814821.
39. Ackerley, N.; Brewster, A. G.; Brown, G. R.; Clarke, D. S.; Foubister, A. J.; Griffin, S. J.; Hudson, J. A.; Smithers, M. J.; Whittamore, P. R. O. J. Med. Chem. 1995, 38 (10), 1608-1628.
40. Nielson, S. F.; Larsen, M.; Boesen, T.; Schønning, K.; Kromann, H. J. Med. Chem. 2005, 48 (7), 2667-2677.