Riluzole prodrugs for melanoma and ALS: Design, synthesis, and in vitro metabolic profiling

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 18, 2012, Pages 5642-5648

  McDonnell, Mark E ^a   Vera, Matthew D ^a   Blass, Benjamin E ^a   Pelletier, Jeffrey C ^a   King, Richard C ^b   Fernandez Metzler, Carmen ^b   Smith, Garry R ^a   Wrobel, Jay ^a   Chen, Suzie ^c   Wall, Brian A ^c   Reitz, Allen B ^a  

^a Fox Chase Chemical Diversity Center Inc   (United States)

^b PharmaCadence Analytical Services   (United States)

^c RUTGERS UNIVERSITY   (United States)

Author keywords

Cancer; Cyp1A2; Melanoma; Prodrug; Riluzole

Indexed keywords

(6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)CARBAMIC ACID 2 DIMETHYLAMINO ETHYL ESTER; (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)CARBAMIC ACID 3 (DIMETHYLAMINO)PROPYL ESTER; (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)CARBAMIC ACID BUTYL ESTER; (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)CARBAMIC ACID ETHYL ESTER; (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)CARBAMIC ACID HEXYL ESTER; (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)CARBAMIC ACID ISOBUTYL ESTER; (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)CARBAMIC ACID METHYL ESTER; (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)CARBAMIC ACID PROPYL ESTER; 2 (1 AMINOMETHYL CYCLOHEXYL) N (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)ACETAMIDE; 2 (2 NITROPHENYL) N (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)ACETAMIDE; 2 AMINO 3 BENZYLOXY N (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)PROPIONAMIDE; 2 AMINO 3 METHYL N (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)BUTYRAMIDE; 2 AMINO 3 PHENYL N (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)PROPIONAMIDE; 2 AMINO N (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)PROPIONAMIDE; 5 AMINOPENTANOIC ACID (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)AMIDE; CYTOCHROME P450 1A2; N (2 MORPHOLIN 4 YL ETHYL) N' (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)SUCCINAMIDE; N (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)SUCCINAMIC ACID; N (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)SUCCINAMIC ACID METHYL ESTER; N (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)SUCCINAMIC ACID TERT BUTYL ESTER; N PYRIDIN 3 YLMETHYL N' (6 TRIFLUOROMETHOXYBENZOTHIAZOL 2 YL)SUCCINAMIDE; O BENZYLSERINE DERIVATIVE; PRODRUG; RILUZOLE; UNCLASSIFIED DRUG;

AMYOTROPHIC LATERAL SCLEROSIS; ANTINEOPLASTIC ACTIVITY; ARTICLE; DIGESTIVE SYSTEM; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DESIGN; DRUG IDENTIFICATION; DRUG METABOLISM; DRUG RELEASE; DRUG SCREENING; DRUG STABILITY; DRUG SYNTHESIS; DRUG TRANSPORT; FIRST PASS EFFECT; HUMAN; IN VITRO STUDY; IN VIVO STUDY; INTESTINE FLUID; MELANOMA; NONHUMAN; PROTEIN EXPRESSION; STOMACH JUICE; TUMOR XENOGRAFT;

AMYOTROPHIC LATERAL SCLEROSIS; ANIMALS; CYTOCHROME P-450 CYP1A2; DRUG DESIGN; DRUG STABILITY; HUMANS; MELANOMA; MICE; MICROSOMES, LIVER; MOLECULAR STRUCTURE; PRODRUGS; RILUZOLE;

EID: 84866237660     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.07.004     Document Type: Article

References (32)

1. E.A. Cavalheiro, and J.W. Olney Proc. Natl. Acad. Sci. USA 98 2001 5947
2. T. Takano, J.H. Lin, G. Arcuino, Q. Gao, J. Yang, and M. Nedergaard Nat. Med. 7 2001 1010
3. N. Kalariti, N. Pissimissis, and M. Koutsilieris Expert Opin. Investig. Drugs 14 2005 1487
4. J. Ackermann, and F. Beermann Pigment Cell Res. 18 2005 315
5. W. Rzeski, C. Ikonomidou, and L. Turski Biochem. Pharmacol. 64 2002 1195
6. W. Rzeski, L. Turski, and C. Ikonomidou Proc. Natl. Acad. Sci. USA 98 2001 6372
7. A. Stepulak, M. Sifringer, and W. Rzeski Proc. Natl. Acad. Sci. USA 102 2005 15605
8. A. Doble Neurology 47 1996 233S
9. B.D. Kretschmer, U. Kratzer, and W.J. Schmidt Naunyn-Schmiedebergs Arch Pharmacol. 358 1998 181
10. S.J. Wang, K.Y. Wang, and W.C. Wang Neuroscience 125 2004 191
11. J. Namkoong, S.S. Shin, and H.J. Lee Cancer Res. 67 2007 2298
12. J.H. Shuff, M.L. Siker, M.D. Daly, and C.J. Schultz Clin Plas. Surg. 37 2010 147
13. V.A. Trinh Am. J. Health Syst. Pharm. 65 2008 3
14. V.K. Sondak, and L.E. Flaherty Nat. Rev. Clin. Oncol. 8 2011 513
15. J.J. Luke, and F.S. Hodi Clin. Cancer Res. 18 2012 9
16. G. Bensimon, L. Lacomblez, and V. Meininger N. Engl. J. Med. 330 1994 585
17. D. Yip, M.N. Le, J.L.-K. Chan, J.H. Lee, J.A. Mehnert, A. Yudd, J. Kempf, W.J. Shih, S. Chen, and J.S. Goydos Clin. Cancer Res. 15 2009 3896
18. G.J. Groeneveld, H.J.M. Van Kan, and S. Kalmijn Neurology 61 2003 1141
19. H.J.M. van Kan, G.J. Groeneveld, S. Kalmijn, M. Spieksma, L.H. van den Berg, and H.J. Guchelaar Brit. J. Clin. Pharmacol. 59 2004 310
20. G.J. Sanderink, B. Bournique, J. Stevens, M. Petry, and M. Martinet J. Pharmacol. Exp. Ther. 282 1997 1465
21. M. Martinet, G. Montay, and G. Rhodes Drugs Today 33 1997 587
22. P. Ettmayer, G.L. Amidon, B. Clement, and B. Testa J. Med. Chem. 47 2004 2393
23. J. Rautio, H. Kumpulainen, and T. Heimbach Nat. Rev. Drug Disc. 7 2008 255
24. B. Testa Biochem. Pharmacol. 68 2004 2097
25. K. Fredholt, N. Mork, and M. Begtrup Int. J. Pharm. 123 1995 209
26. N.-H. Nam, Y. Kim, Y.-J. You, D.-H. Hong, H.-M. Kim, and B.-Z. Ahn Bioorg. Med. Chem. 11 2003 1021
27. B.M. Sykes, G.J. Atwell, A. Hogg, W.R. Wilson, C.J. O'Connor, and W.A. Denny J. Med. Chem. 42 1999 346
28. L. Di, and E.H. Kerns Curr. Opin. Drug Disc. Devel. 8 2005 495
29. R.B. Baudy, J.A. Butera, M.A. Abou-Gharbia, H. Chen, B. Harrison, U. Jain, R. Magolda, J.Y. Sze, M.R. Brandt, T.A. Cummons, D. Kowal, M.N. Pangalos, B. Zupan, U.M. Hoffmann, M. May, C. Mugford, J. Kennedy, and W.E. Childers Jr. J. Med. Chem. 52 2009 771
30. M.E. Jung, and G. Piizzi Chem. Rev. 105 2005 1735
31. A.K. Mandagere, T.N. Thompson, and K.-K. Hwang J. Med. Chem. 45 2002 304
32. Assays performed by Absorption Systems, Inc. Exton, PA.