Design and synthesis of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. Part 4: Biological evaluation of imidazobenzodiazepines as potent PARP-1 inhibitors for treatment of ischemic injuries

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 17, 2003, Pages 3695-3707

  Ferraris, Dana ^a   Ficco, Rica Pargas ^a   Dain, David ^a   Ginski, Mark ^a   Lautar, Susan ^a   Lee Wisdom, Kathy ^a   Liang, Shi ^a   Lin, Qian ^a   Lu, May X C ^a   Morgan, Lisa ^a   Thomas, Bert ^a   Williams, Lawrence R ^a   Zhang, Jie ^a   Zhou, Yinong ^a   Kalish, Vincent J ^a  

^a GUILFORD PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (5 BENZYL 2,5 DIAZABICYCLO[2.2.1]HEPT 2 YLMETHYL) 8,9 DIHYDRO 7H 2,7,9A TRIAZABENZO[CD]AZULEN 6 ONE; 1 DIMETHYLAMINOMETHYL 8,9 DIHYDRO 7H 2,7,9A TRIAZABENZO[CD]AZULEN 6 ONE; 1 PHENETHYL 8,9 DIHYDRO 7H 2,7,9A TRIAZABENZO[CD]AZULEN 6 ONE; 1 [4 (3 DIMETHYLAMINOPROPOXY)PHENYL] 8,9 DIHYDRO 7H 2,7,9A TRIAZABENZO[CD]AZULEN 6 ONE; AMINE; BENZODIAZEPINE DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BRAIN INFARCTION; BRAIN ISCHEMIA; CATALYSIS; CONTROLLED STUDY; DIABETES MELLITUS; DRUG ACTIVITY; DRUG DESIGN; DRUG INDICATION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; EXPERIMENTAL MODEL; GLUCOSE BLOOD LEVEL; HYDROGEN BOND; MALE; MOUSE; NONHUMAN; PROTEIN DOMAIN; RAT; STRUCTURE ACTIVITY RELATION;

EID: 12444286415     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00333-X     Document Type: Article

References (41)

1. Decker P., Isenberg D., Muller S. J. Biol. Chem. 275:2000;9043.
2. Herceg Z., Wang Z.Q. Mol. Cell. Biol. 19:1999;5124.
3. Yu S.-W., Wang H., Poitras M.F., Coombs C., Bowers W.J., Federoff H.J., Poirer G.G., Dawson T.M., Dawson V.L. Science. 297:2002;259.
4. Menissier-de Murcia J., Molinete M., Gradwohl G., Simonin F., de Murcia G. J. Mol. Biol. 210:1989;229.
5. Rolli V., O'Farrell M., Menissier-de Murcia J., de Murcia G. Biochemistry. 36:1997;12147.
6. Jeggo P.A. Curr. Biol. 8:1998;R49.
7. Griffin R.J., Pemberton L.C., Rhodes D., Bleasdale C., Bowman K., Calvert A.H., Curtin N.J., Durkacz B.W., Newell D.R., Porteous J.K. Anti-Cancer Drug Des. 10:1995;507.
8. Nagayama T., Simon R.P., Chen D., Henshall D.C., Pei W., Stetler R.A., Chen J. J. Neurochem. 74:2000;1636.
9. Takahashi K., Pieper A.A., Croul S.E., Zhang J., Snyder S.H., Greenberg J.H. Brain Res. 829:1999;46.
10. Eliasson M.J., Sampei K., Mandir A.S., Hurn P.D., Traystman R.J., Bao J., Pieper A., Wang Z.Q., Dawson T.M., Snyder S.H., Dawson V.L. Nat. Med. 3:1997;1089.
11. Pieper A.A., Walles T., Wei G., Clements E.E., Verma A., Snyder S.H., Zweier J.L. Mol. Med. 6:2000;271.
12. Szabo C., Dawson V.L. Trends Pharmacol. Sci. 19:1998;287.
13. Soriano F.G., Pacher P., Mabley J., Liaudet L., Szabo C. Circ. Res. 89:2001;684.
14. Burkart V., Wang Z.Q., Radons J., Heller B., Herceg Z., Stingl L., Wagner E.F., Kolb H. Nat Med. 5:1999;314.
15. Akiyama T., Takasawa S., Nata K., Kobayashi S., Abe M., Shervani N.J., Ikeda T., Nakagawa K., Unno M., Matsuno S., Okamoto H. Proc. Natl. Acad. Sci. U.S.A. 98:2001;48.
16. Watson C.Y., Whish W.J.D., Threadgill M.D. Bioorg. Med. Chem. 6:1998;721.
17. Suto M.J., Turner W.R., Arundel-Suto C.M., Werbel L.M., Sebolt-Leopold J.S. Anti-Cancer Drug Des. 7:1991;107.
18. Li J.H., Serdyuk L., Ferraris D.V., Xiao G., Tays K., Kletzly P.W., Li W., Lautar S., Zhang J., Kalish V. Bioorg. Med. Chem. Lett. 11:2001;1687.
19. Abdelkarim G.E., Gertz K., Harms C., Katchanov J., Dirnagl U., Szabo C., Endres M. Int. J. Mol. Med. 7:2001;255.
20. White A.W., Almassy R., Calvert A.H., Curtin N.J., Griffin R.J., Hostomsky Z., Maegley K., Newell D.R., Srinivasan S., Golding B.T. J. Med. Chem. 43:2000;4084.
21. Banasik M., Komura H., Shimoyama M., Ueda K. J. Biol. Chem. 267:1992;1569.
22. Li H., Goldstein B.M. J. Med. Chem. 35:1992;3560.
23. Skalitzky D.J., Marakovits J.T., Maegley K.A., Ekker A., Yu X.-H., Hostomsky Z., Webber S.E., Eastman B.W., Almassy R., Li J., Curtin N.J., Newell D.R., Calvert A.H., Griffin R.J., Golding B.T. J. Med. Chem. 46:2003;210.
24. Canan Koch S.S., Thoresen L.H., Jayashree G.T., Maegley K.A., Almassy R.J., Li J., Yu X.-H., Zook S.E., Kumpf R.A., Zhang C., Boritzki T.J., Mansour R.N., Zhang K.E., Ekker A., Calabrese C.R., Curtin N.J., Kyle S., Thomas H.D., Wang L.-Z., Calvert A.H., Golding B.T., Griffin R.J., Newell D.R., Webber S.E., Homstomsky Z. J. Med. Chem. 45:2002;4961.
25. Kukla M.J., Breslin H.J., Pauwels R., Fedde C.L., Miranda M., Scott M.K., Sherrill R.G., Raeymaekers A., Van Gelder J., Andries K., Janssen M.A., De Clercq E., Janssen P.A.J. J. Med. Chem. 34:1991;746.
26. Denny W.A., Rewcastle G.W., Baguley B.C. J. Med. Chem. 33:1990;814.
27. McDonald M.C., Mota-Filipe H., Wright J.A., Abdelrahman M., Threadgill M.D., Thompson A.S., Thiemermann C. Br. J. Pharmacol. 130:2000;843.
28. Geneste P., Kamenka J.-M., Vidal Y., Fauquet J.-P., Morel M.E., Muller P., Warolin C. Eur. J. Med. Chem. 13:1978;53.
29. Ruf A., Rolli V., de Murcia G., Schulz G.E. J. Mol. Biol. 278:1998;57.
30. Ruf A., de Murcia G., Schulz G.E. Biochemistry. 37:1998;3893.
31. Constantino G., Macchiarulo A., Camaioni E., Pelliciari R. J. Med. Chem. 44:2001;3786.
32. Mandagere A.K., Thompson T.N., Hwang K.-K. J. Med. Chem. 45:2002;304.
33. Arturrson P. J. Pharm. Sci. 79:1990;476.
34. Belayev L. Stroke. 27:1996;1616.
35. Chen S.T. Stroke. 17:1986;738.
36. Breslin H.J., Kukla M.J., Ludovici D.W., Mohrbacher R., Ho W., Miranda M., Rodgers J.D., Hitchens T.K., Leo G., Gauthier D.A., Ho C.Y., Scott M.K., De Clercq E., Rauwels R., Andries K., Janssen M.A., Janssen P.A.J. J. Med. Chem. 38:1995;771.
37. Ruf A., de Murcia J.M., de Murcia G.M., Schultz G.E. Proc. Natl. Acad. Sci. U.S.A. 93:1996;7481.
38. Halgren T. J. Comp. Chem. 20:1999;720.
39. Fleisher D. Peptide-based Drug Design: Controlling Transport and Metabolism. 1995;American Chemical Society, Washington, DC.
40. Tokunaga H., Yoneda Y., Kuriyama K. Eur. J. Pharmacol. 87:1983;237.
41. Takahashi K., Greenberg J.H., Jackson P., Maclin K., Zhang J. J. Cereb. Blood Flow Metab. 17:1997;1137.