1982
K. Ushiroda et al. / Bioorg. Med. Chem. Lett. 21 (2011) 1978–1982
6. Ushiroda, K.; Maruta, K.; Kitoh, M.; Iwai, K.; Nagamine, J.; Tsuchida, A.; Taiji, M.;
Nagata, R. Bioorg. Med. Chem. Lett. 2011, 21, 220.
Willson, T. M. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 13919; (b) Nolte, R. T.;
Wisely, G. B.; Westin, S.; Cobb, J. E.; Lambert, M. H.; Kurokawa, R.; Rosenfeld,
M. G.; Willson, T. M.; Glass, C. K.; Milburn, M. V. Nature 1998, 395, 137; (c)
Cronet, P.; Petersen, J. F. W.; Folmer, R.; Blomberg, N.; Sjöblom, K.; Karlsson, U.;
Lindstedt, E.-L.; Bamberg, K. Structure 2001, 9, 699.
7. All new compounds gave consistent 1H NMR spectra and satisfactory LC/MS
data. Experimental procedures for the analogs reported here are disclosed in
WO2004048341.
8. Bastiaansen, L. A. M.; Godefroi, E. F. Synthesis 1978, 9, 675.
14. (a) Bruning, J. B.; Chalmers, M. J.; Prasad, S.; Busby, S. A.; Kamenecka, T. M.; He,
Y.; Nettles, K. W.; Griffin, P. R. Structure 2007, 15, 1258; (b) Einstein, M.;
Akiyama, T. E.; Castriota, G. A.; Wang, C. F.; McKeever, B.; Mosley, R. T.; Becker,
J. W.; Moller, D. E.; Meinke, P. T.; Wood, H. B.; Berger, J. P. Mol. Pharmacol. 2008,
73, 62; (c) Östberg, T.; Svensson, S.; Selén, G.; Uppenberg, J.; Thor, M.;
Sundbom, M.; Sydow-Bäckman, M.; Gustavsson, A.; Jendeberg, L. J. Biol. Chem.
2004, 279, 41124; (d) Burgermeister, E.; Schnoebeien, A.; Flament, A.; Benz, J.;
Stihle, M.; Gsell, B.; Rufer, A.; Ruf, A.; Kuhn, B.; Märki, H. P.; Mizrahi, J.;
Sebokova, E.; Niesor, E.; Meyer, M. Mol. Endocrinol. 2006, 20, 809.
9. Mitsunobu, O.; Kato, K.; Kakese, F. Tetrahedron Lett. 1969, 29, 2473.
10. Hosseinzadeh, R.; Tajbakhsh, M.; Alikarami, M. Synlett 2006, 13, 2124.
11. Transactivation assay: COS-1 cells were inoculated in 24-well plates
(5 Â 104 cells/well) and cultured for approximately 24 h in Dulbecco’s
modified Eagle’s essential medium (DMEM) supplemented with 10%
charcoal-treated fetal calf serum in 5% CO2 at 37 °C. The cells were
transfected with each expression plasmid for a fusion protein of the ligand
binding domain of PPAR and GAL4, and a GAL4-responsive luciferase reporter
plasmid by lipofection, using Lipofectamine™ and Plus™ Reagent. Culture
medium was removed 4 h after the initiation of transfection, followed by
addition of medium containing the test substance (1 mL/well), and the cells
were then cultured in a CO2 incubator at 37 °C with 5% CO2. No drug control
cells were added with DMSO concentration of 0.1% as final. After 24 h, cells
were lysed and the luciferase activity was measured in a luminometer.
12. Metaglidasen: (a) Zhang, F.; Clemens, L. E.; Gregoire, F. M.; Udove, J.; Bell, A.;
Mu, Y.; Chandalia, A.; Gustafson, T. A. Diabetes Mol. Gen. Signal Path. Integr.
Physiol. (January 14–19, Keystone) 2007, Abstr. 344.; INT-131: (b) Motani, A.;
Wang, Z.; Weiszmann, J.; McGee, L. R.; Lee, G.; Liu, Q.; Staunton, J.; Fang, Z.;
Fuentes, H.; Lindstrom, M.; Liu, J.; Biermann, D. H. T.; Jaen, J.; Walker, N. P. C.;
Learned, R. M.; Chen, J.-L.; Li, Y. J. Mol. Biol. 2009, 386, 1301; nTZDpa: (c) Berger,
J. P.; Petro, A. E.; Macnaul, K. L.; Kelly, L. J.; Zhang, B. B.; Richards, K.; Elbrecht,
A.; Johnson, B. A.; Zhou, G.; Doebber, T. W.; Biswas, C.; Parikh, M.; Sharma, N.;
Tanen, M. R.; Thompson, G. M.; Ventre, J.; Adams, A. D.; Mosley, R.; Surwit, R.
S.; Moller, D. E. Mol. Endocrinol. 2003, 17, 662.
15. db/db mice were used as described in: Berger, J.; Bailey, P.; Biswas, C.; Cullinan,
C. A.; Doebber, T. W.; Hayes, N. S.; Saperstein, R.; Smith, R. G.; Liebowitz, M. D.
Endocrinology 1996, 137, 4189.
16. (a) Chaput, E.; Saladin, R.; Silvestre, M.; Edgar, A. D. Biochem. Biophys. Res.
Commun. 2000, 271, 445; (b) Carmona, M. C.; Louche, K.; Nibbelink, M.; Prunet,
B.; Bross, A.; Desbazeille, M.; Dacquet, C.; Renard, P.; Casteilla, L.; Penicaud, L.
Int. J. Obes. 2005, 29, 864; (c) Fu, J.; Gaetani, S.; Ovelsi, F.; Verme, J. L.; Serrano,
A.; Rodriguez de Fonseca, F.; Rosengarth, A.; Luecke, H.; Giacomo, B. D.; Tarzia,
G.; Piomelli, D. Nature 2003, 425, 90; (d) Cano, C.; Pavon, J.; Serrano, A.; Goya,
P.; Paez, J. A.; Rodriguez de Fonseca, F.; Macias-Gonzalez, M. J. Med. Chem. 2007,
50, 389; (e) O’Sullivan, S. E. Br. J. Pharmacol. 2007, 152, 576.
17. (a) Allen, T.; Zhang, F.; Moodie, S. A.; Clemens, L. E.; Smith, A.; Gregoire, F.; Bell,
A.; Muscat, G. E.; Gustafson, T. A. Diabetes 2006, 55, 2523; (b) Acton, J. J.; Black,
R. M.; Jones, A. B.; Moller, D. E.; Colwell, L.; Doebber, T. W.; MacNaul, K. L.;
Berger, J.; Wood, H. B. Bioorg. Med. Chem. Lett. 2005, 15, 357; (c) Benson, S. C.;
Pershadsingh, H. A.; Ho, C. I.; Chittiboyina, A.; Desai, P.; Pravenec, M.; Qi, N.;
Wang, J.; Avery, M. A.; Kurtz, T. W. Hypertension 2004, 43, 993.
13. (a) Xu, H. E.; Lambert, M. H.; Montana, V. G.; Plunket, K. D.; Moore, L. B.; Collins,
J. B.; Oplinger, J. A.; Kliewer, S. A.; Gampe, R. T.; McKee, D. D.; Moore, J. T.;