Identification of novel allosteric nonpeptidergic inhibitors of the human cytomegalovirus-encoded chemokine receptor US28

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 2, 2010, Pages 675-688

  Vischer, Henry F ^a   Hulshof, Janneke W ^a   Hulscher, Saskia ^a   Fratantoni, Silvina A ^a   Verheij, Mark H P ^a   Victorina, Jane ^a   Smit, Martine J ^a   de Esch, Iwan J P ^a   Leurs, Rob ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Chemokine; Constitutive activity; HCMV; Herpesvirus; Inverse agonist; Nonpeptidergic; Viral GPCR

Indexed keywords

1 (4,4 BIS[4 FLUOROPHENYL)BUTYL] 4 (4 CHLOROPHENYL)PIPERIDIN 4 OL; 1 [2 (2,4 DICHLOROBENZYL) 2,3 DIHYDRO 1H INDEN 1 YL] 4 METHYLPIPERAZINE; 1 [2 (2,4 DICHLOROBENZYL) 2,3 DIHYDRO 1H INDEN 1 YL] 4 PHENYLPIPERAZINE; 1 [2 (2,4 DICHLOROBENZYL) 2,3 DIHYDRO 1H INDEN 1 YL]PIPERIDINE; 1 [2 (BENZHYDRYLOXY)ETHYL] 4 (4 CHLOROPHENYL)PIPERIDIN 4 OL FUMARATE; 1 [3 [(4 CHLOROBENZYL)(PHENYL)AMINO]PROPYL] 4 (4 CHLOROPHENYL)PIPERIDIN 4 OL FUMARATE; 1 [3 [BENZYL(4 CHLOROPHENYL)AMINO]PROPYL] 4 (4 CHLOROPHENYL)PIPERIDIN 4 OL HEMIFUMARATE; 1 [3 [BENZYL(PHENYL)AMINO]PROPYL] 4 (4 CHLOROPHENYL)PIPERIDIN 4 OL HEMIFUMARATE; 2 (2 METHOXYBENZYL) 2,3 DIHYDRO 1H INDEN 1 AMINE; 2 (2,4 DIMETHOXYBENZYL) 2,3 DIHYDRO 1H INDEN 1 AMINE; 2 (2,4 DIMETHYLBENZYL) 2,3 DIHYDRO 1H INDEN 1 AMINE; 2 (4 METHOXY 3 METHOXYBENZYL) 2,3 DIHYDRO 1H INDEN 1 AMINE; 2 (4 METHOXYBENZYL) 2,3 DIHYDRO 1H INDEN 1 AMINE; 2 BENZYL 2,3 DIHYDRO 1H INDEN 1 AMINE; 3 (4 CHLOROPHENYL) 1 [3 [11,12 DIHYDRODIBENZO[B,F]AZOCIN 5(6H) YL]PROPYL]PIPERIDIN 3 OL FUMARATE; 4 (4 CHLOROPHENYL) 1 [2 (2,4 DICHLOROBENZYL) 2,3 DIHYDRO 1H INDEN 1 YL] 1,2,3,6 TETRAHYDROPYRIDINE; 4 (4 CHLOROPHENYL) 1 [2 (2,4 DICHLOROBENZYL) 2,3 DIHYDRO 1H INDEN 1 YL] PIPERIDIN 4 OL; 4 (4 CHLOROPHENYL) 1 [2 [8 (METHYLTHIO) 10,11 DIHYDRODIBENZO[B,F]THIEPIN 10 YLOXY]ETHYL]PIPERIDIN 4 OL FUMARATE; 4 (4 CHLOROPHENYL) 1 [3 [11,12 DIHYDRODIBENZO[B,F]AZOCIN 5(6H) YL]PROPYL]PIPERIDINE 4 OL FUMARATE; 5 (3 CHLOROPROPYL) 5,6,11,12 TETRAHYDRODIBENZO[B,F]AZOCINE; 5 [4 (4 CHLOROPHENYL) 4 HYDROXY PIPERIDIN 1 YL] 2,2 DIPHENYLPENTANENITRILE; [4 (4 CHLOROPHENYL) 1 [3 [11,12 DIHYDRODIBENZO[B,F]AZOCIN 5(6H) YL]PROPYL]PIPERIDIN 4 YL]METHANAMINE FUMARATE; CHEMOKINE RECEPTOR; CHEMOKINE RECEPTOR AGONIST; CHEMOKINE RECEPTOR US28; CLOROTEPINE; METITEPINE; N [4 [(1 AMINO 2,3 DIHYDRO 1H INDEN 2 YL)METHYL]PHENYL]ACETAMIDE; N BENZYL 2 (2,4 DICHLOROBENZYL) 2,3 DIHYDRO 1H INDEN 1 AMINE FUMARATE; UNCLASSIFIED DRUG; VUF 2274;

ARTICLE; CYTOMEGALOVIRUS; DRUG IDENTIFICATION; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; NONHUMAN; PROTEIN BINDING; STRUCTURE ACTIVITY RELATION; TUMOR GROWTH;

AMINES; HUMANS; IMIPRAMINE; INDENES; LIGANDS; MOLECULAR STRUCTURE; RECEPTORS, CHEMOKINE; STRUCTURE-ACTIVITY RELATIONSHIP; VIRAL PROTEINS;

HERPESVIRIDAE; HUMAN HERPESVIRUS 5;

EID: 76449101555     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.11.060     Document Type: Article

References (25)

1. Billstrom M.A., Lehman L.A., and Scott Worthen G. Am. J. Respir. Cell Mol. Biol. 21 (1999) 163
2. Bodaghi B., Jones T.R., Zipeto D., Vita C., Sun L., Laurent L., Arenzana-Seisdedos F., Virelizier J.L., and Michelson S. J. Exp. Med. 188 (1998) 855
3. Fraile-Ramos A., Kledal T.N., Pelchen-Matthews A., Bowers K., Schwartz T.W., and Marsh M. Mol. Biol. Cell. 12 (2001) 1737
4. Soderberg-Naucler C. J. Int. Med. 259 (2006) 219
5. Casarosa P., Bakker R.A., Verzijl D., Navis M., Timmerman H., Leurs R., and Smit M.J. J. Biol. Chem. 276 (2001) 1133
6. Waldhoer M., Kledal T.N., Farrell H., and Schwartz T.W. J. Virol. 76 (2002) 8161
7. McLean K.A., Holst P.J., Martini L., Schwartz T.W., and Rosenkilde M.M. Virology 325 (2004) 241
8. Maussang D., Verzijl D., van Walsum M., Leurs R., Holl J., Pleskoff O., Michel D., van Dongen G.A., and Smit M. J. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 13068
9. Casarosa P., Menge W.M., Minisini R., Otto C., van Heteren J., Jongejan A., Timmerman H., Moepps B., Kirchhoff F., Mertens T., Smit M.J., and Leurs R. J. Biol. Chem. 278 (2003) 5172
10. Hulshof J.W., Casarosa P., Menge W.M., Kuusisto L.M., van der Goot H., Smit M.J., de Esch I.J., and Leurs R. J. Med. Chem. 48 (2005) 6461
11. Hulshof J.W., Vischer H.F., Verheij M.H., Fratantoni S.A., Smit M.J., de Esch I.J., and Leurs R. Bioorg. Med. Chem. 14 (2006) 7213
12. Schall, T. J.; McMaster, B. E.; Dairaghi, D. J. World (PTC) Patent WO0217969, 2002.
13. Schall, T. J.; McMaster, B. E.; Dairaghi, D. J. World (PTC) Patent WO0217900, 2002.
14. McMaster, B. E.; Schall, T. J.; Penfold, M. E.; Wright, J. J.; Dairaghi, D. J. World (PTC) Patent WO03018549, 2003.
15. Buzas A., Champagnac A., Dehnel A., Lavielle G., and Pommier M. J. Med. Chem. 23 (1980) 149
16. Monro A.M., Quinton R.M., and Wrigley T.I. J. Med. Chem. 6 (1963) 255
17. Kwartler C.E., and Lucas P. J. Am. Chem. Soc. 69 (1947) 2582
18. Kumagai T., Okubo T., Kataoka-Okubo H., Chaki S., Okuyama S., and Nakazato A. Bioorg. Med. Chem. 9 (2001) 1349
19. Jilek J., Pomykacek J., Dlabac A., Bartosova M., and Protiva M. Coll. Czech. Chem. Commun. 45 (1980) 504
20. Jilek J.O., Metysova J., Pomykacek J., and Protiva M. Coll. Czech. Chem. Commun. 39 (1974) 3338
21. Bartl V., Jilek J., Metysova J., Valchar M., Dlabac A., Wildt S., and Protiva M. Coll. Czech. Chem. Commun. 49 (1984) 1810
22. Houlihan W.J., Shapiro M.J., and Chin J.A. J. Org. Chem. 62 (1997) 1529
23. Thompson A.S., Humphrey G.R., DeMarco A.M., Mathre D.J., and Grabowski E.J. J. Org. Chem. 58 (1993) 5886
24. Gu X.H., Yu H., Jacobson A.E., Rothman R.B., Dersch C.M., George C., Flippen-Anderson J.L., and Rice K.C. J. Med. Chem. 43 (2000) 4868
25. Smits R.A., Lim H.D., Stegink B., Bakker R.A., de Esch I.J., and Leurs R. J. Med. Chem. 49 (2006) 4512