Y. Maeda et al. / Bioorg. Med. Chem. Lett. 14 (2004) 3907–3911
3911
2
. GSK-3b is known to phosphorylate the microtubule
associated protein tau in mammalian cells. Lovestone,
S.; Reynolds, C. H.; Latimer, D.; Davis, D. R.; Anderton,
B. H.; Gallo, J.-M.; Hanger, D.; Mulot, S.; Marquardt, B.
Curr. Biol. 1994, 4, 1077.
American Chemical Society: Washington, DC, 2003,
MEDI22; (h) Olesen, P. H.; Sorensen, A. R.; Urso, B.;
Kurtzhals, P.; Bowler, U. E.; Hansen, B. F. [Triazole
derivative]. J. Med. Chem. 2003, 46, 3333; (i) Gallet, T.;
Lardenois, P.; Lochead, A. W.; Nedelec, A.; Marguerie,
S.; Saady, M.; Yaiche, P. [6,7,8,9-tetrahydropyrimido(1,2-
3
. GSK-3b binds to presenilin 1 and its binding complex
mediates b-amyloid-induced neurotoxicity. Planel, E.;
Sun, X.; Takashima, A. Drug Develop. Res. 2002, 56, 491.
. (a) Leclerc, S.; Garnier, M.; Hoessel, R.; Marko, D.; Bibb,
J. A.; Snyder, G. L.; Greengard, P.; Biernat, J.; Wu, Y. Z.;
Mandelkow, E. M.; Eisenbrand, G.; Meijer, L. [Indiru-
bin]. J. Biol. Chem. 2001, 276, 251; (b) Leost, M.; Schultz,
C.; Link, A.; Wu, Y. Z.; Biernat, J.; Mandelkow, E. M.;
Bibb, J. A.; Snyder, G. L.; Greengard, P.; Zaharevitz, D.
W.; Gussio, R.; Senderowicz, A. M.; Sausville, E. A.;
Kunick, C.; Meijer, L. [Paullone]. Eur. J. Biochem. 2000,
a)pyrimidin-4-one].
European
Patent
Application
EP1295885, 2003; (j) Kuo, G.-H.; Prouty, C.; DeAngelis,
A.; Shen, L.; O’Neil, D. J.; Shah, C.; Connolly, P. J.;
Murray, W. V.; Conway, B. R.; Cheung, P.; Westover, L.;
Xu, J. Z.; Look, R. A.; Demarest, K. T.; Emanuel, S.;
Middleton, S. A.; Jolliffe, L.; Beavers, M. P.; Chen, X.
4
[Macrocyclic
imides]. J. Med. Chem. 2003, 46, 4021.
polyoxy-genated
bis-7-azaindolylmale-
5. Adams, J. J.; Bryan, D. D.; Feng, Y.; Matsunaga, S.;
Miyazaki, Y.; Nakano, M.; Rocher, J.-P.; Sato, H.;
Semones, M.; Silvia, D. J.; Tang, J. PCT International
Application WO 03/022852, 2003.
6. Witherington, J.; Boardas, V.; Haigh, D.; Hickey, D. M.;
Ife, R. J.; Rawlings, A. D.; Slingsby, B. P.; Smith, D. G.;
Ward, R. W. Bioorg. Med. Chem. Lett. 2003, 13, 1581.
7. Docking model of 1 was made by using Quanta/
CHARMm (Accelrys Inc., San Diego, CA, USA).
8. hGSK-3b enzyme assay was carried out by scintillation
proximity assay (SPA).
2
67, 5983; (c) Smith, D. G.; Buffet, M.; Fenwick, A. E.;
Haigh, D.; Ife, R. J.; Saunders, M.; Slingsby, B. P.; Stacey,
R.; Ward, R. W. [Maleimide, SB-415286]. Bioorg. Med.
Chem. Lett. 2001, 11, 635; (d) Meijer, L.; Thunnissen, A.
M. W. H.; White, A. W.; Garnier, M.; Nikolic, M.; Tsai,
L. H.; Walter, J.; Cleverley, K. E.; Salinas, P. C.; Wu, Y.
Z.; Biernat, J.; Mandelkow, E. M.; Kim, S. H.; Pettit, G.
R. [Hymenialdisine]. Chem. Biol. 2000, 7, 51; (e) Naerum,
L.; Norskov-lauritsen, L.; Olesen, P. H. [5-(1-pyridyl)-
[
(
1,3,4]-oxadiaol]. Bioorg. Med. Chem. Lett. 2002, 12, 1525;
f) Martinez, A.; Aloso, M.; Castro, A.; Perez, C.;
Moreno, F. J. [Thiadiazolidinone]. J. Med. Chem. 2002,
5, 1292; (g) Wagman, A. S.; Harrison, S. D.; Johnson, K.;
9. Davis, S. P.; Reddy, H.; Caivano, M.; Cohen, P. Biochem.
J. 2000, 351, 95.
10. In-house X-ray crystal structure data.
11. The method of the glycogen accumulation assay in L6 cells
was described by: Peat, A. J.; Garrido, D.; Boucheron, J.
A.; Schweiker, S. L.; Dickerson, S. H.; Wilson, J. R.;
Wang, T. Y.; Thomson, S. A. Bioorg. Med. Chem. Lett.
2004, 14, 2127.
4
Ring, D. B.; Bussiere, D. E.; Nuss, J. M.; Pfister, K. B.;
Goff, D.; Boyce, R. S.; Ramurthy, S.; Brown, S. P.;
Renhowe, P. A.; Subramanian, S.; Zhou, X. A.
[CHIR73911]. In 225th National Meeting of the American
Chemical Society, New Orleans, LA, March 23–27, 2003;
12. Several experimental conditions are available in Ref. 5.