Design and synthesis of a G-protein-coupled receptor antagonist library of aryloxyalkanolamines using a polymer-supported acyclic acetal linker

Journal of Combinatorial Chemistry

Volumn 11, Issue 1, 2009, Pages 72-82

  Roberge, Jacques Y ^a   Harikrishnan, Lalgudi S ^a   Kamau, Muthoni G ^a   Ruan, Zheming ^a   Van Kirk, Katy ^a   Liu, Yalei ^a   Cooper, Christopher B ^a   Poss, Michael A ^a   Dickson Jr , John K ^a   Gavai, Ashvinikumar V ^a   Chao, Sam T ^a   Leith, Leslie W ^a   Bednarz, Mark S ^a   Mathur, Arvind ^a   Kakarla, Ramesh ^a   Schnur, Dora M ^a   Vaz, Roy ^a   Lawrence, R Michael ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CROSS LINKING REAGENT; G PROTEIN COUPLED RECEPTOR; POLYMER; PROPANOLAMINE DERIVATIVE;

ARTICLE; COMBINATORIAL CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; HUMAN; MOLECULAR LIBRARY; SYNTHESIS;

AMINES; COMBINATORIAL CHEMISTRY TECHNIQUES; CROSS-LINKING REAGENTS; DRUG DESIGN; HUMANS; POLYMERS; PROPANOLAMINES; RECEPTORS, G-PROTEIN-COUPLED; SMALL MOLECULE LIBRARIES;

EID: 60849108926     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc800051u     Document Type: Article

References (44)

1. Klabunde, T.; Hessler, G. ChemBioChem 2002, 3, 928-944.
2. Venter, J. C.; Adams, M. D.; Myers, E. W.; Li, P. W.; Mural, R. J.; Sutton, G. G.; Smith, H. 6.; Yandell, M.; Evans, C. A.; Holt, R. A.; Gocayne, J. D.; Amanatides, P.; Ballew, R. M.; Huson, D. H.; Wormian, J. R.; Zhang, Q.; Kodira, C. D.; Zheng, X. H.; Chen, L.; Skupski, M.; G. Subramanian, G.; Thomas, P. D.; Zhang, J.; Gabor Miklos, G. L.; Nelson, C.; Broder, S.; Clark, A. G.; Nadeau, J.; McKusick, V. A.; Zinder, N.; Levine, A. J.; Roberts, R. J.; Simon, M.; Slayman, C.; Hunkapiller, M.; Bolanos, R.; Delcher, A.; Dew, L.; Fasulo, D.; Flanigan, M.; Florea, L.; Halpern, A.; Hannenhalli, S.; Kravitz, S.; Levy, S.; Mobarry, C.; Reinert, K.; Rernington, K.; Abu-Threideh, J.; Beasley, E.; Biddick, K.; Bonazzi, V.; Brandon, R.; Cargill, M.; Chandramouliswaran, L.; Charlab, R.; Chaturvedi, K.; Deng, Z.; Di Francesco, V.; Dunn, P.; Eilbeck, K.; Evangelista, C.; Gabrielian, A. E.; Gan, W.; Ge, W.; Gong, F.; Gu, Z.; Guan, P.; Heiman, T. J.; Higgins, M. E.; Ji, R. R.; Ke, Z.; Ketchum, K. A.; Lai, Z.; Lei, Y.; Li, Z.; Li, J.; Liang, Y.; Lin, X.; Lu, F.; Merkulov, G. V.; Milshina, N.; Moore, H. M.; Naik, A. K.; Narayan, V. A.; Neelam, B.; Nusskern, D.; Rusch, D. B.; Salzberg, S.; Shao, W.; Shue, B.; Sun, J.; Wang, Z.; Wang, A.; Wang, X.; Wang, J.; Wei, M.; Wides, R.; Xiao, C.; Yan, C.; Yao, A.; Ye, J.; Zhan, M.; Zhang, W.; Zhang, H.; Zhao, Q.; Zheng, L.; Zhong, F.; Zhong, W.; Zhu, S.; Zhao, S.; Gilbert, D.; Baumhueter, S.; Spier, G.; Carter, C.; Cravchik, A.; Woodage, T.; Ali, F.; An, H.; Awe, A.; Baldwin, D.; Baden, H.; Barnstead, M.; Barrow, I.; Beeson, K.; Busam, D.; Carver, A.; Center, A.; Cheng, M. L.; Curry, L.; Danaher, S.; Davenport, L.; Desilets, R.; Dietz, S.; Dodson, K.; Doup, L.; Ferriera, S.; Garg, N.; Gluecksmann, A.; Hart, B.; Haynes, J.; Haynes, C.; Heiner, C.; Hladun, S.; Hostin, D.; Houck, J.; Howland, T.; Ibegwam, C.; Johnson, J.; Kalush, F.; Kline, L.; Koduru, S.; Love, A.; Mann, F.; May, D.; McCawley, S.; Mcintosh, T.; McMullen, L.; Moy, M.; Moy, L.; Murphy, B.; Nelson, K.; Pfannkoch, C.; Pratts, E.; Puri, V.; Qureshi, H.; Reardon, M.; Rodriguez, R.; Rogers, Y. H.; Romblad, D.; Ruhfel, B.; Scott, R.; Sitter, C.; Smallwood, M.; Stewart, E.; Strong, R.; Suh, E.; Thomas, R.; Tint, N. N.; Tse, S.; Vech, C.; Wang, G.; Wetter, J.; Williams, S.; Williams, M.; Windsor, S.; Winn-Deen, E.; Wolfe, K.; Zaveri, J.; Zaveri, K.; Abril, J. F.; Guigo, R.; Campbell, M. J.; Sjolander, K. V.; Karlak, B.; Kejariwal, A.; Mi, H.; Lazareva, B.; Hatton, T.; Narechania, A.; Diemer, K.; Muruganujan, A.; Guo, N.; Sato, S.; Bafna, V.; Istrail, S.; Lippert, R.; Schwartz, R.; Walenz, B.; Yooseph, S.; Allen, D.; Basu, A.; Baxendale, J.; Blick, L.; Caminha, M.; Carnes-Stine, J.; Caulk, P.; Chiang, Y. H.; Coyne, M.; Dahlke, C.; Mays, A.; Dombroski, M.; Donnelly, M.; Ely, D.; Esparham, S.; Fosler, C.; Gire, H.; Glanowski, S.; Glasser, K.; Glodek, A.; Gorokhov, M.; Graham, K.; Gropman, B.; Harris, M.; Heil, J.; Henderson, S.; Hoover, J.; Jennings, D.; Jordan, C.; Jordan, J.; Kasha, J.; Kagan, L.; Kraft, C.; Levitsky, A.; Lewis, M.; Liu, X.; Lopez, J.; Ma, D.; Majoros, W.; McDaniel, J.; Murphv, S.; Newman, M.; Nguyen, T.; Nguven, N.; Nodell, M. Science 2001, 291, 1304-1351.
3. The Merck Index, 13th ed.; Merck: Whitehouse Station, NJ, 2001.
4. Van Niel, M. B.; Beer, M. S.; Castro, J.; Cheng, S. K. F.; Evans, D. C.; Heald, A.; Hitzel, L.; Hunt, P.; Mortishire-Smith, R.; O'Connor, D. Bioorg. Med. Chem. Lett. 1999, 9, 3243-3248.
5. Leznoff, C. C.; Wong, J. Y. Can. J. Chem. 1972, 50, 2892M-2893.
6. (a) Farrall, M. J.; Frechet, J. M. J. .J. Org. Chem. 1976, 41, 3877-3882.
7. (b) Chan, T. H.; Huang, W. Q. J. Chem. Soc., Chem. Comm. 1985, 909-911.
8. (c) Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307-1309.
9. (a) Frechet, J. M. J.; Nuyens, L. J. Can. J. Chem. 1976, 54, 926-934.
10. (b) Fyles, T. M.; Leznoff, C. C. Can. J. Chem. 1976, 54, 935-942.
11. (a) Stones, D.; Miller, D. J.; Beaton, M. W.; Rutherford, T. J.; Gani, D. Tetrahedron Lett. 1998, 39, 4875-4878.
12. (b) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383.
13. (a) Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 733-736.
14. (b) Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 737-740.
15. (a) Thompson, L. A.; Ellman, Jonathan A. Tetrahedron Lett. 1994, 35, 9333-9336.
16. (b) Yoo, S.-e.; Gong, Y.-D.; Choi, M.-Y.; Seo, J.-s.; Yang, Yi, K. Tetrahedron Lett. 2000, 41, 6415-6418.
17. (c) Watanabe, Y.; Ishikawa, S.; Takao, G.; Toru, T. Tetrahedron Lett. 1999, 40, 3411-3414.
18. Nicolaou, K. C.; Zipkin, R.; Tanner, D. J. Chem. Soc., Chem. Commun. 1984, 349-350.
19. Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772-3774.
20. Dujardin. G.; Rossignol, S.; Brown, E. Tetrahedron Lett. 1995, 36, 1653-1656.
21. Lei, P.-s.; Ogawa, Y.; Kovac, P. J. Carbohydrate Chem. 1996, 15, 485-500.
22. Leigh, D. A.; Martin, R. P.; Smart, J. P.; Truscello, A. M. J. Chem. Soc., Chem. Commun. 1994 137, 3-1374.
23. Mettler-Toledo, http://us.mt.com/home (accessed May 2007).
24. Landauer, S. R.; Rydon, H. N. Chem. Ind. 1951, 313.
25. Hudson, H. R.; Powroznyk, L. ARKIVOC 2004, 19-33.
26. MDL Available Chemicals Directory MDL. http://www.mdli. com/products/experiment/available-chem-dir/index.jsp (accessed March 2001).
27. 21 Tripos Sybyl Line Notation; TRIPOS: St Louis, MO; http:// www.tripos.com (accessed March 2001).
28. (a) Bernis, G. W.; Murcko, M. A. J. Med. Chem. 1996, 39, 2887-2893.
29. (b) Mason. J. S.; Morize, I.; Menard, P. R.; Cheney, D. L.; Hulme, C.; Labaudiniere, R. F. J. Med. Chem. 1999, 42, 3251-3264.
30. (c) Schnur, D.; Beno Brett, R.; Good, A.; Tebben, A. Approaches to target class combinatorial library design In Methods in Molecular Biology; Bajorath, J., Ed.; Humana Press: Clifton, NJ, 2004; Vol. 275, pp 355-378.
31. MDL Drug Data Report. http://www.mdli.com/products/ knowledge/drug-data- report/index.jsp (accessed March 2001).
32. (a) Schnur, D. M.; Hermsmeier, M. Recent approaches to target class design. Presented at the 36th Mid Atlantic Regional Meeting of the American Chemical Society, Princeton, NJ, 2003.
33. (b) Bondensgaard, K.; Ankersen, M.; Thogersen, H.; Hansen, B. S.; Wulff, B. S.; Bywater, R. P. J. Med. Chem. 2004, 47, 888-899.
34. (a) Hansch, C.; Leo, A., Calculation of octanol-water partition coefficients by fragments In Exploring QSAR: Fundamentals and Applications in Chemistry and Biology; American Chemical Society: Washington, DC, 1995; pp 125-168.
35. (b) Mason, J. S.; Morize, I.; Menard, P. R.; Cheney, D. L.; Hulme, C.; Labaudiniere, R. F. .J. Med. Chem. 1999, 42, 3251-3264.
36. (c) ClogP; Biobyte Corp.: Mission Viejo, CA 1995, http:// www.clogp@biobyte.com (accessed March 2001).
37. Sybyl, 6.7; Tripos: St-Louis, MO, 2002.; http://www.tripos.com.
38. CombiLibMaker; Tripos: St-Louis, MO; http://www.tripos. com (accessed March 2001).
39. (a) Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 1997, 23, 3-25.
40. (b) Lipinski, C. A. Drug Discovery Today: Technol. 2004, 1, 337-341.
41. Irori Nanokans. http://www.irori.com/Products/irori-tech-nanokan.html (accessed March 2001).
42. Rydon, H. N. Org. Synth. 1971, 51, 44-47.
43. Fang, L.; Wan, M.; Pennacchio, M.; Pan, J. J. Comb. Chem. 2000, 2, 254-257.
44. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.