Tetrabutylammonium fluoride-assisted rapid N9-alkylation on purine ring: Application to combinatorial reactions in microtiter plates for the discovery of potent sulfotransferase inhibitors in situ

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 15, 2005, Pages 4622-4626

  Brik, Ashraf ^a   Wu, Chung Yi ^a   Best, Michael D ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

N alkylation; Purine based libraries; Sulfotransferase inhibitors; TBAF

Indexed keywords

ALCOHOL DERIVATIVE; FLUORINE DERIVATIVE; ORGANOHALOGEN DERIVATIVE; PURINE; SULFOTRANSFERASE INHIBITOR; TETRABUTYLAMMONIUM FLUORIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; COMBINATORIAL CHEMISTRY; DRUG POTENCY; DRUG SYNTHESIS; MICROTITER PLATE ASSAY; MITSUNOBU REACTION; RELIABILITY;

ALKYLATION; COMBINATORIAL CHEMISTRY TECHNIQUES; ENZYME INHIBITORS; MOLECULAR STRUCTURE; PURINES; QUATERNARY AMMONIUM COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFOTRANSFERASES;

EID: 20544464406     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.02.066     Document Type: Article

References (27)

1. J. Vesely, L. Havlicek, M. Strnad, J.J. Blow, A. Donella-Deana, L. Pinna, D.S. Letham, J. Kato, L. Detivaud, and S. Leclerc Eur. J. Biochem. 224 1994 771
2. N.S. Gray, L. Wodicka, A.-M.W.H. Thunnissen, T.C. Norman, S. Kwon, F.H. Espinoza, D.O. Morgan, G. Barnes, S. LeClerc, L. Meijer, S.-H. Kim, D.J. Lockhart, and P.G. Schultz Science 281 1998 533
3. Y.-T. Chang, N.S. Gray, G.R. Rosania, D.P. Sutherlin, S. Kwon, T.C. Norman, R. Sarohia, M. Leost, L. Meijer, and P.G. Schultz Chem. Biol. 6 1999 361
4. S. Ding, N.S. Gray, X. Wu, Q. Ding, and P.G. Schultz J. Am. Chem. Soc. 124 2002 1594
5. S. Ding, N.S. Gray, Q. Ding, X. Wu, and P.G. Schultz J. Comput. Chem. 3 2001 97
6. S. Ding, N.S. Gray, Q. Ding, and P.G. Schultz Tetrahedron Lett. 42 2001 8751
7. S. Ding, N.S. Gray, Q. Ding, and P.G. Schultz J. Org. Chem. 66 2001 8273
8. A. Toyota, N. Katagiri, and C. Kaneko Heterocycles 36 1993 1625
9. J.A. Montgomery, K. Hewson Jr., and C. Temple J. Med. Pharm. Chem. 5 1962 15
10. M.R. Hamden, and R.L. Jarvest Tetrahedron Lett. 26 1985 4265
11. E.J. Corey, and A.J. Venkateswarlu J. Am. Chem. Soc. 94 1972 6190
12. K. Fugami, S.-Y. Ohnuma, M. Kameyama, T. Saotome, and M. Kosugi Synlett 1999 63
13. A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, and Y. Nishihara Org. Lett. 2 2000 2935
14. M.M. Alauddin, J.M. Miller, and J.H. Clark Can. J. Chem. 62 1984 263
15. D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo, and L. Vaccaro J. Org. Chem. 69 2004 2896
16. J.-I. Hayami, N. Uno, and A. Kaji Tetrahedron Lett. 11 1968 1385
17. A. Brik, Y.-C. Lin, J. Elder, and C.-H. Wong Chem. Biol. 9 2002 891
18. T.-J. Cheng, A. Brik, C.-H. Wong, and C.-C. Kan Antimicrob. Agents Chemother. 48 2004 2437
19. A. Brik, J. Muldoon, Y.-C. Lin, J.H. Elder, D.S. Goodsell, A.J. Olson, V.V. Fokin, K.B. Sharpless, and C.-H. Wong ChemBioChem. 4 2003 1246
20. M.D. Best, A. Brik, E. Chapman, L.V. Lee, W.-C. Cheng, and C.-H. Wong ChemBioChem. 5 2004 811
21. C.-Y. Wu, J.-T. Jan, S.-H. Ma, C.-J. Kuo, H.-F. Juan, Y.-S.E. Cheng, H.-H. Hsu, H.-C. Huang, D. Wu, A. Brik, F.-S. Liang, R.-S. Liu, J.M. Fang, S.-T. Chen, P.-H. Liang, and C.-H. Wong Proc. Natl. Acad. Sci. U.S.A. 101 2004 10012
22. L.V. Lee, M.L. Mitchell, S.-J. Huang, V.V. Fokin, K.B. Sharpless, and C.-H. Wong J. Am. Chem. Soc. 125 2003 9588
23. C.-Y. Wu, C.-F. Chang, J.S.-Y. Chen, C.-H. Wong, and C.-H. Lin Angew. Chem., Int. Ed. 42 2003 4661
24. C.F. Chang, C.W. Ho, C.Y. Wu, T.A. Chao, C.-H. Wong, and C.-H. Lin Chem. Biol. 11 2004 1301
25. M.D. Burkart, M. Izumi, E. Chapman, C.-H. Lin, and C.-H. Wong J. Org. Chem. 65 2000 5565
26. E. Chapman, S. Ding, P.G. Schultz, and C.-H. Wong J. Am. Chem. Soc. 124 2002 14524
27. M.D. Burkart, and C.-H. Wong Anal. Biochem. 274 1999 131