6-Position optimization of tricyclic 4-quinolone-based inhibitors of glycogen synthase kinase-3β: Discovery of nitrile derivatives with picomolar potency

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 2, 2012, Pages 1005-1008

  Li, Bei ^a   Cociorva, Oana M ^a   Nomanbhoy, Tyzoon ^a   Li, Qiang ^a   Nakamura, Kai ^a   Nomura, Masahiro ^b   Okada, Kyoko ^b   Yumoto, Kazuhiro ^b   Liyanage, Marek ^a   Zhang, Melissa C ^a   Aban, Arwin ^a   Szardenings, Anna Katrin ^a   Kozarich, John W ^a   Kohno, Yasushi ^b   Shreder, Kevin R ^a  

^a ACTIVX BIOSCIENCES INC   (United States)

^b KYORIN PHARMACEUTICAL CO LTD   (Japan)

Author keywords

4 Quinolone; 6 Nitrile; 6 Tetrazole; GSK 3 inhibitor; Kinase profiling

Indexed keywords

4 QUINOLONE DERIVATIVE; 6 CARBOXYLIC ACID; CARBOXYLIC ACID; GLYCOGEN SYNTHASE KINASE; GLYCOGEN SYNTHASE KINASE 3BETA; GLYCOGEN SYNTHASE KINASE 3BETA INHIBITOR; NITRILE; PHOSPHOTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CONCENTRATION (PARAMETERS); DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; MINIMUM INHIBITORY CONCENTRATION;

ANTI-BACTERIAL AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; ESCHERICHIA COLI; GLYCOGEN SYNTHASE KINASE 3; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; NITRILES; QUINOLIZINES; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84855689377     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.12.006     Document Type: Article

References (17)

1. A. Ali, K.P. Hoeflich, and J.R. Woodgett Chem. Rev. 101 2001 2527
2. M.P. Coghlan, A.A. Culbert, D.A. Cross, S.L. Corcoran, J.W. Yates, N.J. Pearce, O.L. Rausch, G.J. Murphy, P.S. Carter, C.L. Roxbee, D. Mills, M.J. Brown, D. Haigh, R.W. Ward, D.G. Smith, K.J. Murray, A.D. Reith, and J.C. Holder Chem. Biol. 7 2000 793
3. R.V. Bhat, S.L. Budd Haeberlein, and J. Avila J. Neurochem. 89 2004 1313
4. M.K. Rowe, C. Wiest, and D.M. Chuang Neurosci. Biobehav. Rev. 31 2007 920
5. Z. Hilioti, D.A. Gallagher, S.T. Low-Nam, P. Ramaswamy, P. Gajer, T.J. Kingsbury, C.J. Birchwood, A. Levchenko, and K.W. Cunningham Genes Dev. 18 2004 35
6. P.S. Klein, and D.A. Melton Proc. Natl. Acad. Sci. U.S.A. 93 1996 8455
7. R.G. Gentles, S. Hu, and G. Dubowchik Annu. Rep. Med. Chem. 44 2009 736
8. F.X. Tavares, J.A. Boucheron, S.H. Dickerson, R.J. Griffin, F. Preugschat, S.A. Thomson, T.Y. Wang, and H.-Q. Zhou J. Med. Chem. 47 2004 4716
9. H. Zou, L. Zhou, Y. Li, Y. Cui, H. Zhong, Z. Pan, Z. Yang, and J. Quan J. Med. Chem. 53 2010 994
10. O.M. Cociorva, B. Li, T. Nomanbhoy, Q. Li, A. Nakamura, K. Nakamura, M. Nomura, K. Okada, S. Seto, K. Yumoto, M. Liyanage, M.C. Zhang, A. Aban, B. Leen, A.K. Szardenings, J.S. Rosenblum, J.W. Kozarich, Y. Kohno, and K.R. Shreder Bioorg. Med. Chem. Lett. 21 2011 5948
11. F.F. Fleming, L. Yao, P.C. Ravikumar, L. Funk, and B.C. Shook J. Med. Chem. 53 2010 7902
12. R.J. Herr Bioorg. Med. Chem. 10 2002 3379
13. D.S. North, D.N. Fish, and J.J. Reddington Pharmacotherapy 18 1998 915
14. M.K. Bolon Med. Clin. North Am. 95 2011 793
15. M.A. Wikler, F.R. Cockerill III, K. Bush, M.N. Dudley, G.M. Eliopoulos, D.J. Hardy, J.F. Hindler, J.B. Patel, M. Powell, J.D. Turnidge, M.P. Weinstein, B.L. Zimmer, M.J. Ferraro, and J.M. Swenson Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically 2009 Clinical and Laboratory Standards Institute M07-A8
16. M.P. Patricelli, A.K. Szardenings, M. Liyanage, T.K. Nomanbhoy, M. Wu, H. Weissig, A. Aban, D. Chun, Tanner, S, and J.W. Kozarich Biochemistry 46 2007 350
17. M.P. Patricelli, T.K. Nomanbhoy, J. Wu, H. Brown, D. Zhou, J. Zhang, S. Jagannathan, A. Aban, E. Okerberg, C. Herring, B. Nordin, H. Weissig, Q. Yang, J-D. Lee, N.S. Gray, and J.W. Kozarich Chem. Biol. 18 2011 699