Discovery of novel N-aryl piperazine CXCR4 antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 25, Issue 21, 2015, Pages 4950-4955

  Zhao, Huanyu ^a   Prosser, Anthony R ^a   Liotta, Dennis C ^a   Wilson, Lawrence J ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

CXC chemokine receptor 4; CXCR4 antagonists; G protein coupled receptor; HIV; Piperazine

Indexed keywords

CHEMOKINE RECEPTOR CXCR4 ANTAGONIST; N ARYL PIPERAZINE; UNCLASSIFIED DRUG; CHEMOKINE RECEPTOR CXCR4; CXCR4 PROTEIN, HUMAN; CYTOCHROME P450; CYTOCHROME P450 INHIBITOR; ERG1 POTASSIUM CHANNEL; PIPERAZINE; PIPERAZINE DERIVATIVE; POTASSIUM CHANNEL HERG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG IDENTIFICATION; HUMAN IMMUNODEFICIENCY VIRUS 1; IC50; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; VIRUS ENTRY; VIRUS INHIBITION; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG DEVELOPMENT; HUMAN; METABOLISM; SYNTHESIS;

CYTOCHROME P-450 ENZYME INHIBITORS; CYTOCHROME P-450 ENZYME SYSTEM; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; ETHER-A-GO-GO POTASSIUM CHANNELS; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERAZINES; RECEPTORS, CXCR4; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84944173359     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2015.04.036     Document Type: Article

References (37)

1. A. Peled, O. Wald, and J. Burger Expert Opin. Invest. Drugs 21 2012 341
2. T. Lapidot, and I. Petit Exp. Hematol. 30 2002 973
3. T. Sugiyama, H. Kohara, M. Noda, and T. Nagasawa Immunity 25 2006 977
4. Y. Tzeng, H. Li, Y.L. Kang, W.C. Chen, and W.C. Chen Blood 117 2011 429
5. K. Tachibana, S. Hirota, H. Iizasa, H. Yoshia, K. Kawabata, Y. Kataoka, Y. Kitamura, K. Matsushima, N. Yoshida, S. Nishikawa, T. Kishimoto, and T. Nagasawa Nature 393 1998 591
6. Y. Zou, A.H. Kottman, M. Kuroda, I. Taniuchi, and D.R. Littman Nature 393 1998 595
7. T. Nagasawa, K. Tachibana, and K. Kawabata Adv. Immunol. 71 1999 211
8. E. Oberlin, A. Amara, F. Bachelerie, C. Bessia, J.L. Virelizier, F. Arenzana-Seisdedos, O. Schwartz, J.M. Heard, I. Clark-Lewis, D.F. Legler, M. Loetscher, M. Baggiollni, and B. Moser Nature 382 1996 833
9. T. Murakami, and N. Yamamoto Future Microbiol. 5 2010 1025
10. E. De Clercq Nat. Rev. Drug Disc. 2 2003 581
11. J.F. Dipersio, U. Yasothan, and D. Kirkpatrick Nat. Rev. Drug Disc. 8 2009 105
12. S. Hassan, M. Buchanan, K. Jahan, A. Aguilar-Mahecha, L. Gaboury, W.J. Muller, Y. Alsawafi, A.A. Mourskaia, P.M. Siegel, O. Salvucci, and M. Basic Int. J. Cancer 129 2011 225
13. B. Debnath, S. Xu, F. Grande, A. Garofalo, and N. Neamati Theranostics 3 2013 47 10.7150/thno.5376
14. F. Balkwell Nat. Rev. Cancer 4 2004 540
15. A. Zlotnik J. Pathol. 215 2008 211
16. B.A. Teicher, and S.P. Fricker Clin. Cancer Res. 16 2010 2927
17. J.A. Burger, and A. Peled Leukemia 23 2009 43
18. U.M. Domanska, R.C. Kruizinga, W.B. Nagengast, H. Timmer-Bosscha, G. Huls, E.G.E. de Vries, and A.M.E. Walenkamp Eur. J. Cancer 49 2013 219
19. L.J. Wilson, and D.C. Liotta Drug Dev. Res. 72 2011 598
20. H. Tamamura, H. Tsutsumi, W. Nomura, T. Tanaka, and N. Fujii Expert Opin. Drug Discov. 3 2008 1155
21. W.-T. Choi, S. Duggineni, Y. Xu, Z. Huang, and J. An J. Med. Chem. 55 2012 977
22. R.T. Skerlj, G.J. Bridger, A. Kaller, E.J. McEachem, J.B. Crawford, Y. Zhou, B. Atsma, J. Langille, S. Nan, D. Veale, T. Wilson, C. Harwig, S. Hatse, K. Princen, E. DeClercq, and D. Schols J. Med. Chem. 53 2010 3376
23. N.D. Stone, S.B. Dunaway, C. Flexner, C. Tierney, G.B. Calandra, S. Becker, Y.-J. Cao, I.P. Wiggins, J. Conley, R.T. MacFarland, J.-G. Park, C. Lalama, S. Snyder, B. Kallungal, K.L. Klingman, and C.W. Hendrix Antimicrob. Agents Chemother. 51 2007 2351
24. S. Jenkinson, M. Thomson, D. McCoy, M. Edelstein, S. Danehower, W. Lawrence, P. Wheelan, A. Spaltenstein, and K. Gudmundsson Antimicrob. Agents Chemother. 54 2010 817
25. G. Thoma, M.B. Streiff, J. Kovarik, F. Glickman, T. Wagner, C. Beerli, and H.-G. Zerwes J. Med. Chem. 51 2008 7915
26. W. Zhan, Z. Liang, A. Zhu, S. Kurtkaya, H. Shim, J.P. Snyder, and D.C. Liotta J. Med. Chem. 50 2007 5655
27. Z. Liang, W. Zhan, A. Zhu, Y. Yoon, S. Lin, M. Sasaki, J.-M.A. Klapproth, H. Yang, H.E. Grossniklaus, J. Xu, M. Rojas, R.J. Voll, M.M. Goodman, R.F. Arrendale, J. Liu, C.C. Yun, J.P. Snyder, D.C. Liotta, and H. Shim PLoS One 7 2012 e34038
28. V.M. Truax, H. Zhao, B.M. Katzman, A.R. Prosser, A.A. Alcaraz, M.T. Saindane, R.B. Howard, D. Culver, R.F. Arrendale, P.R. Gruddanti, T.J. Evers, M.G. Natchus, J.P. Snyder, D.C. Liotta, and L.J. Wilson ACS Med. Chem. Lett. 4 2013 1025
29. R.V. Patel, and S.W. Park Mini Rev. Med. Chem. 13 2013 1579
30. C.P. Meher, A.M. Rao, and Md. Omar AJPSR 3 2013 43
31. J. Kimpton, and M. Emerman J. Virol. 66 1992 2232
32. C. Lackman-Smith, C. Osterling, K. Luckenbaugh, M. Mankowski, B. Snyder, G. Lewis, J. Paull, A. Profy, R.G. Ptak, R.W. Buckheit, K.M. Watson, J.E. Cummins, and B.E. Sanders-Beer Antimicrob. Agents Chemother. 52 2008 1768
33. GPCR Profiler Assay. Eurofins/Panlabs Discovery Services, St. Charles, MO.
34. B. Wu, E.Y.T. Chien, C.D. Mol, G. Fenalti, W. Liu, V. Katritch, R. Abagyan, A. Brooun, P. Wells, F.C. Bi, D.J. Hamel, P. Kuhn, T.M. Handel, V. Cherezov, and R.C. Stevens Science 330 2010 1066
35. B.D. Cox, A.R. Prosser, B.M. Katzman, A.A. Alcaraz, D.C. Liotta, L.J. Wilson, and J.P. Snyder ChemBioChem 15 2014 1614
36. M. Nyunt, S. Becker, R.T. MacFarland, P. Chee, R. Scarborough, S. Everts, G.B. Calandra, and C.W. Hendrix J. Acquir. Immune Defic. Syndr. 47 2008 559
37. Y.J. Cao, C.W. Flexner, S. Dunaway, J.G. Park, K. Klingman, I. Wiggins, J. Conley, C. Radebaugh, A.D. Kashuba, R.T. MacFarland, S. Becker, and C.W. Hendrix Antimicrob. Agents Chemother. 52 2008 1630