2-Aryl-2,2-difluoroacetamide FKBP12 Ligands: Synthesis and X-ray Structural Studies

Organic Letters

Volumn 3, Issue 25, 2001, Pages 3987-3990

  Dubowchik, Gene M ^a   Vrudhula, Vivekananda M ^a   Dasgupta, Bireshwar ^a   Ditta, Jonathan ^a   Chen, Ti ^a   Sheriff, Steven ^a,b   Sipman, Karin ^a,b   Witmer, Mark ^a,b   Tredup, Jeffrey ^a,b   Vyas, Dolatrai M ^a   Verdoorn, Todd A ^a   Bollini, Sagarika ^a   Vinitsky, Alexander ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; FK 506 BINDING PROTEIN; FLUORINATED HYDROCARBON; IMMUNOSUPPRESSIVE AGENT; LIGAND; TSUKUBAENOLIDE;

ANIMAL; ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN BINDING; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACETAMIDES; ANIMAL; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; HYDROCARBONS, FLUORINATED; IMMUNOSUPPRESSIVE AGENTS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN BINDING; TACROLIMUS; TACROLIMUS BINDING PROTEIN 1A; TACROLIMUS BINDING PROTEINS;

EID: 18044403602     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0166909     Document Type: Article

References (28)

1. Galat, A. Eur. J. Biochem. 1993, 216, 689.
2. Schreiber, S. L. Science 1991, 251, 283.
3. Gaburjakova, M.; Gaburjakova, J.; Reiken, S.; Huang, F.; Marx, S. O.; Rosemblit, N.; Marks, A. R. J. Biol. Chem. 2001, 276, 16931.
4. Huse, M.; Chen, Y.-G.; Massague, J.; Kuriyan, J. Cell 1999, 96, 425.
5. Lyons, W. E.; Steiner, J. P.; Snyder, S. H.; Dawson, T. M. J. Neurosci. 1995, 15, 2985.
6. (a) Hamilton, G. S.; Steiner, J. P. J. Med. Chem. 1998, 41, 5119.
7. (b) Gold, B. G. Mol. Neurobiol. 1997, 15, 285.
8. (c) Gold, B. G.; Densmore, V.; Shou, W.; Matzuk, M. M.; Gordon, H. S. J. Pharmacol. Exp. Ther. 1999, 289, 1202.
9. Costantini, L. C.; Isacson, O. Exp. Neurol. 2000, 164, 60.
10. Ross, D. T.; Guo, H.; Howorth, P.; Chen, Y.; Hamilton, G. S.; Steiner, J. P. Neurosci. Lett. 2001, 297, 113.
11. (a) Harper, S.; Bilsland, J.; Young, L.; Bristow, L.; Boyce, S.; Mason, G.; Rigby, M.; Hewson, L.; Smith, D.; O'Donnell, R.; O'Connor, D.; Hill, R. G.; Evans, D.; Swain, C.; Williams, B.; Hefti, F. Neuroscience 1999, 88, 257.
12. (b) Becker, D. B.; Jensen, J. N.; Myckatyn, T. M.; Doolabh, V. B.; Hunter, D. A.; Mackinnon, S. E. J. Reconstr. Microsurg. 2000, 16, 613.
13. Sauer, H.; Francis, J. M.; Jiang, H.; Hamilton, G. S.; Steiner, J. P. Brain Res. 1999, 842, 109.
14. Hasler, D. W.; Jensen, L. T.; Zerbe, O.; Winge, D. R.; Vasak, M. Biochemistry 2000, 39, 14567.
15. Armistead, D. M.; Badia, M. C.; Deininger, D. D.; Duffy, J. P.; Saunders: J. O.; Tung, R. D.; Thomson, J. A.; Decenzo, M. T.; Futer, O.; Livingston, D. J.; Murcko, M. A.; Yamashita, M. M.; Navia, M. A. Acta Crystallogr., Sect. D 1995, 51, 522.
16. Taylor, M. J.; Hoffman, T. Z.; Yli-Kauhaluoma, J. T.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1998, 120, 12783.
17. (a) Holt, D. A.; Luengo, J. I.; Yamashita, D. S.; Oh, H. J.; Konialian, A. L.; Yen, H. K.; Rozamus, L. W.; Brandt, M.; Bossard, M. J.; Levy, M. A.; Eggleston, D. S.; Liang, J.; Schultz, L. W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 9925.
18. (b) Dubowchik, G. M.; Ditta, J.; Herbst, J. J.; Bollini, S.; Vinitsky, A. Bioorg. Med. Chem. Lett. 2000, 10, 559.
19. Davies-Coleman, M. T.; Faulkner, D. J.; Dubowchik, G. M.; Roth, G. P.; Poison, C.; Fairchild, C. J. Org. Chem. 1993, 58, 5925.
20. 2: C, 67.29; H, 6.78; N, 4.48; F, 6.08. Found: C, 67.40; H, 6.85; N, 4.23; F, 5.86.
21. Sich, C.; Cowley, D. J.; Guenet, C.; Merly, J. P.; Tuefel, M.; Saudek, V. Eur. J. Biochem. 2000, 267, 5342.
22. Kofron, J. L.; Kuzmic, P.; Kishore, V.; Colon-Bonilla, E.; Rich, D. H. Biochemistry 1991, 30, 6127.
23. The lack of FKBP12 inhibitory activity of related compounds in which the ketone carbonyl has been replaced by methylene has been demonstrated previously: Wang, G. T.; Lane, B.; Fesik, S. W.; Petros, A.; Luly, J.; Krafft, G. A. Bioorg. Med. Chem. Lett. 1994, 4, 1161.
24. Hamilton, G. S.; Steiner, J. P. Curr. Pharm. Des. 1997, 3, 405.
25. Dunitz, J. D.; Taylor, R. Chem. Eur. J. 1997, 3, 89.
26. Barbarich, T. J.; Rithner, C. D.; Miller, S. M.; Anderson, O. P.; Strauss, S. H. J. Am. Chem. Soc. 1999, 121, 4280 and leading references therein.
27. DerHovanessian, A.; Doyon, J. B.; Jain, A.; Rablen, P. R.; Sapse, A.-M. Org. Lett. 1999, 1, 1359.
28. Groves, M. R.; Yao, Z. J.; Roller, P. P.; Burke, T. R.; Barford, D. Biochemistry 1998, 37, 17773. Associated PDB assession number: 1BZC.