Novel indole-based inhibitors of IMPDH: Introduction of hydrogen bond acceptors at indole C-3

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 7, 2003, Pages 1273-1276

  Watterson, Scott H ^a   Dhar, T G Murali ^a   Ballentine, Shelley K ^a   Shen, Zhongqi ^a   Barrish, Joel C ^a   Cheney, Daniel ^a   Fleener, Catherine A ^a   Rouleau, Katherine A ^a   Townsend, Robert ^a   Hollenbaugh, Diane L ^a   Iwanowicz, Edwin J ^a  

^a BRISTOL MYERS SQUIBB PHARMACEUTICAL RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; INDOLE; INDOLE DERIVATIVE; INOSINATE DEHYDROGENASE; INOSINATE DEHYDROGENASE INHIBITOR;

ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; HYDROGEN BOND; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION;

EID: 0037424695     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00109-4     Document Type: Article

References (29)

1. Zimmerman A.G., Gu J.J., Laliberte J., Mitchell B.S. Prg. Nucleic Acid Res. Mol. Biol. 61:1998;181.
2. Jackson R.C., Weber G. Nature. 256:1975;331.
3. Sintchak M.D., Nimmesgern E. Immunopharmacology. 47:2000;163.
4. Hedstrom L. Curr. Med. Chem. 6:1999;545.
5. Collart F.R., Huberman E. J. Biol. Chem. 263:1988;15769.
6. Natsumeda Y., Ohno S., Kawasaki H., Konno Y., Weber G., Suzuki K. J. Biol. Chem. 265:1990;5292.
7. Collart, F. R.; Huberman, E. US Patent 5,665,583, 1997; Chem Abstr. 1990, 113, 186070.
8. Jayaram H.N., Grusch M., Cooney D.A., Krupitza G. Curr. Med. Chem. 6:1999;561.
9. Carr S.F., Papp E., Wu J.C., Natsumeda Y. J. Biol. Chem. 268:1993;27286.
10. Anderson W.K., Boehm T.L., Makara G.M., Swann R.T. J. Med. Chem. 39:1996;46.
11. Nelson P.H., Eugui E., Wang C.C., Allison A.C. J. Med. Chem. 33:1990;833.
12. Sievers T.M., Rossi S.J., Ghobrial R.M., Arriola E., Nishimura P., Kawano M., Holt C.D. Pharmacotherapy. 17:1997;1178.
13. Papageorgiou C. Mini-Rev. Med. Chem. 1:2001;71.
14. Shipkova M., Wieland E., Schutz E., Wiese C., Niedmann P.D., Oellerich M., Armstrong V.W. Transplant. Proc. 33:2001;1080.
15. Dhar T.G.M., Shen Z., Guo J., Liu C., Watterson S.H., Gu H.H., Pitts W.J., Fleener C.A., Rouleau K.A., Sherbina N.Z., McIntyre K.W., Witmer M.R., Tredup J.A., Chen B.-C., Zhao R., Bednarz M.S., Cheney D.L., MacMaster J.F., Miller L.M., Berry K.K., Harper T.W., Barrish J.C., Hollenbaugh D.L., Iwanowicz E.J. J. Med. Chem. 45:2002;2127.
16. Armistead, D. M.; Badia, M. C.; Bemis, G. W.; Bethiel, R. S.; Frank, C. A.; Novak, P. M.; Ronkin, S. M.; Saunders, J. O. PCT Int. Appl., WO 9740028, 1997; Chem Abstr. 1997, 128, 3680.
17. Jain J., Almquist S.J., Shlyakhter D., Harding M.W. J. Pharm. Sci. 90:2001;625.
18. Watterson S.H., Liu C., Dhar T.G.M., Gu H.H., Pitts W.J., Barrish J.C., Fleener C.A., Rouleau K., Sherbina N.Z., Hollenbaugh D., Iwanowicz E.J. Bioorg. Med. Chem. Lett. 12:2002;2879.
19. Iwanowicz E.J., Watterson S.H., Liu C., Gu H.H., Barrish J.C., Fleener C.A., Rouleau K., Sherbina N.Z., Hollenbaugh D. Bioorg. Med. Chem. Lett. 12:2002;2931.
20. Gu H.H., Iwanowicz E.J., Guo J., Watterson S.H., Zhen Z., Pitts W.J., Dhar T.G.M., Fleener C.A., Rouleau K., Sherbina N.Z., Witmer M., Tredup J., Hollenbaugh D. Bioorg. Med. Chem. Lett. 12:2002;1323.
21. Pitts W.J., Guo J., Dhar T.G.M., Shen Z., Gu H.H., Watterson S.H., Bednarz M.S., Chen B.-C., Barrish J.C., Bassolino D., Cheney D., Fleener C.A., Rouleau K.A., Hollenbaugh D.L., Iwanowicz E.J. Bioorg. Med. Chem. Lett. 12:2002;2137.
22. Watterson S.H., Carlsen C., Dhar T.G.M., Shen Z., Pitts W.J., Guo J., Gu H.H., Norris D., Chorba J., Chen P., Cheney D., Witmer M., Fleener C.A., Rouleau K., Townsend R., Hollenbaugh D., Iwanowicz E.J. Bioorg. Med. Chem. Lett. 13:2003;543.
23. Dhar T.G.M., Watterson S.H.;, Chen P., Shen Z., Gu H.H., Norris D., Carlsen M., Haslow K., Pitts W.J., Guo J., Chorba J., Fleener C.A., Rouleau K., Townsend R., Hollenbaugh D., Iwanowicz E.J. Bioorg. Med. Chem. Lett. 13:2003;547.
24. Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 50:1975;4467.
25. Rodriguez A.L., Koradin C., Dohle W., Knochel P. Angew. Chem., Int. Ed. 39:2000;2488.
26. Takahashi S., Kuroyama Y., Sonogashira K., Hagihara N. Synthesis. 1980;627.
27. Hynes, J. Jr.; Leftheris, K.; Watterson, S. H. unpublished work in our laboratories.
28. The IMPDH enzymatic inhibition protocol is outlined in ref 22 (ref 27).
29. The CEM proliferation protocol is outlined in ref 18 (ref 21).