3-Biphenylimidazo[1,2-a]pyridines or [1,2-b]pyridazines and analogues, novel Flaviviridae inhibitors

European Journal of Medicinal Chemistry

Volumn 64, Issue , 2013, Pages 448-463

  Enguehard Gueiffier, Cécile ^a   Musiu, Simone ^b   Henry, Nicolas ^a   Véron, Jean Baptiste ^a   Mavel, Sylvie ^a   Neyts, Johan ^b   Leyssen, Pieter ^b   Paeshuyse, Jan ^b   Gueiffier, Alain ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antiviral agent; BVDV; HCV; Imidazo 1,2 a pyridine imidazo 1,2 b pyridazine

Indexed keywords

[3 (20 HYDROXYBIPHEN 3 YL) 2 (2 METHOXYPHENYL) 6 (THIEN 3 YL)IMIDAZO(1,2 B)PYRIDAZINE]; [3 (BIPHEN 3 YL) 2 (4 FLUOROPHENYL) 6 PHENYLTHIOIMIDAZO(1,2 A)PYRIDINE]; ANTIVIRUS AGENT; IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CROSS RESISTANCE; FLAVIVIRUS; NONHUMAN; PESTIVIRUS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION;

ANTIVIRAL AGENTS; DIARRHEA VIRUSES, BOVINE VIRAL; DOSE-RESPONSE RELATIONSHIP, DRUG; HEPACIVIRUS; IMIDAZOLES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PYRIDAZINES; PYRIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

EID: 84877603515     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.03.054     Document Type: Article

References (28)

1. V.E. Buckwold, B.E. Beer, and R.O. Donis Bovine viral diarrhea virus as a surrogate model of hepatitis C virus for the evaluation of antiviral agents Antiviral Res. 60 2004 1 15
2. B.D. Lindenbach, and C.M. Rice Flaviviridae: the viruses and their replication fourth ed. D.M. Knipe, P.M. Howley, D.E. Griffin, M.A. Martin, R.A. Lamb, B. Roizman, S.E. Straus, Fields Virology vol. 1 2001 Lippincott Williams & Wilkins Philadelphia 991 1041
3. T. Adachi, H. Ago, N. Habuka, K. Okuda, M. Komatsu, S. Ikeda, and K. Yatsunami The essential role of C-terminal residues in regulating the activity of hepatitis C virus RNA-dependent RNA polymerase Biochim. Biophys. Acta 1601 2002 38 48 (Pubitemid 38234529)
4. S. Edwards, A. Fukusho, P.C. Lefevre, A. Lipowski, Z. Pejsak, P. Roehe, and J. Westergaard Classical swine fever: the global situation Vet. Microbiol. 73 2000 103 119 (Pubitemid 30227286)
5. A.L. Lindberg Bovine viral diarrhoea virus infections and its control Vet. Q. 25 2003 1 16 (Pubitemid 36367829)
6. R. Vrancken, A. Haegeman, J. Dewulf, J. Paeshuyse, G. Puerstinger, M. Tignon, M.F. Le Potier, J. Neyts, and F. Koenen The reduction of CSFV transmission to untreated pigs by the pestivirus inhibitor BPIP: a proof of concept Vet. Microbiol. 139 2009 365 368
7. R. Vrancken, A. Haegeman, J. Paeshuyse, G. Puerstinger, J. Rozenski, M. Wright, M. Tignon, M.F. Le Potier, J. Neyts, and F. Koenen Proof of concept for the reduction of classical swine fever infection in pigs by a novel viral polymerase inhibitor J. Gen. Virol. 90 2009 1335 1342
8. Anonymous Global surveillance and control of hepatitis C. Report of a WHO Consultation organized in collaboration with the Viral Hepatitis Prevention Board, Antwerp, Belgium J. Viral. Hepat. 6 1999 35 47
9. A.A. Butt, and F. Kanwal Boceprevir and telaprevir in the management of hepatitis C virus-infected patients Clin. Infect. Dis. 54 2012 96 104
10. T. Asselah, and P. Marcellin Liver Int. 32 2012 88 102
11. L. Delang, L. Coelmont, and J. Neyts Antiviral therapy for hepatitis C virus: beyond the standard of care Viruses-Basel 2 2010 826 866
12. J.-B. Véron, H. Allouchi, C. Enguehard-Gueiffier, R. Snoeck, G. Andrei, E. De Clercq, and A. Gueiffier Influence of 6- or 8-substitution on the antiviral activity of 3-arylalkylthiomethylimidazo[1,2-a]pyridine against human cytomegalovirus (CMV) and varicella-zoster virus (VZV): part II Bioorg. Med. Chem. 16 2008 9536 9545
13. J.-B. Véron, C. Enguehard-Gueiffier, R. Snoeck, G. Andrei, E. De Clercq, and A. Gueiffier Influence of 6- or 8-substitution on the antiviral activity of imidazo[1,2-a]pyridines derivatives against human cytomegalovirus and varicella-zoster virus Bioorg. Med. Chem. 15 2007 7209 7219 (Pubitemid 47451777)
14. J.M. Vrolijk, A. Kaul, B.E. Hansen, V. Lohmann, B.L. Haagmans, S.W. Schalm, and R. Bartenschlager A replicon-based bioassay for the measurement of interferons in patients with chronic hepatitis C J. Virol. Methods 110 2003 201 209 (Pubitemid 36645265)
15. G. Puerstinger, J. Paeshuyse, E. De Clercq, and J. Neyts Antiviral 2,5-disubstituted imidazo[4,5-c]pyridines: from anti-pestivirus to anti-hepatitis C virus activity Bioorg. Med. Chem. Lett. 17 2007 390 393 (Pubitemid 46073753)
16. G. Puerstinger, J. Paeshuyse, P. Herdewijn, J. Rozenski, E. De Clercq, and J. Neyts Substituted 5-benzyl-2-phenyl-5H-imidazo[4,5-c]pyridines: a new class of pestivirus inhibitors Bioorg. Med. Chem. Lett. 16 2006 5345 5349 (Pubitemid 44332215)
17. I. Vliegen, J. Paeshuyse, T. De Burghgraeve, L.S. Lehman, M. Paulson, I.H. Shih, E. Mabery, N. Boddeker, E. De Clercq, H. Reiser, D. Oare, W.A. Lee, W.D. Zhong, S. Bondy, G. Puerstinger, and J. Neyts Substituted imidazopyridines as potent inhibitors of HCV replication J. Hepatol. 50 2009 999 1009
18. J. Paeshuyse, C. Letellier, M. Froeyen, H. Dutartre, R. Vrancken, B. Canard, E. De Clercq, A. Gueiffier, J.C. Teulade, P. Herdewijn, G. Puerstinger, F. Koenen, P. Kerkhofs, P.G. Baraldi, and J. Neyts A pyrazolotriazolopyrimidinamine inhibitor of bovine viral diarrhea virus replication that targets the viral RNA-dependent RNA polymerase Antiviral Res. 82 2009 141 147
19. J. Paeshuyse, P. Leyssen, E. Mabery, N. Boddeker, R. Vrancken, M. Froeyen, I.H. Ansari, H. Dutartre, J. Rozenski, L.H. Gil, C. Letellier, R. Lanford, B. Canard, F. Koenen, P. Kerkhofs, R.O. Donis, P. Herdewijn, J. Watson, E. De Clercq, G. Puerstinger, and J. Neyts A novel, highly selective inhibitor of pestivirus replication that targets the viral RNA-dependent RNA polymerase J. Virol. 80 2006 149 160
20. S.G. Baginski, D.C. Pevear, M. Seipel, S.C. Sun, C.A. Benetatos, S.K. Chunduru, C.M. Rice, and M.S. Collett Mechanism of action of a pestivirus antiviral compound Proc. Natl. Acad. Sci. U. S. A. 97 2000 7981 7986 (Pubitemid 30460759)
21. J. Paeshuyse, J.M. Chezal, M. Froeyen, P. Leyssen, H. Dutartre, R. Vrancken, B. Canard, C. Letellier, T. Li, H. Mittendorfer, F. Koenen, P. Kerkhofs, E. De Clercq, P. Herdewijn, G. Puerstinger, A. Gueiffier, O. Chavignon, J.C. Teulade, and J. Neyts The imidazopyrrolopyridine analogue AG110 is a novel, highly selective inhibitor of pestiviruses that targets the viral RNA-dependent RNA polymerase at a hot spot for inhibition of viral replication J. Virol. 81 2007 11046 11053 (Pubitemid 47536077)
22. C. Enguehard, H. Allouchi, A. Gueiffier, and S.L. Buchwald Easy access to novel substituted 6-aminoimidazo[1,2-a]pyridines using palladium- and copper-catalyzed aminations J. Org. Chem. 68 2003 4367 4370 (Pubitemid 36622722)
23. C. Enguehard, M. Hervet, H. Allouchi, J.-C. Debouzy, J.-M. Léger, and A. Gueiffier Reactivity of a 6-chloroimidazo[1,2-b]pyridazine derivative towards Suzuki cross-coupling reaction Synthesis 4 2001 595 600 (Pubitemid 32293593)
24. C. Enguehard, M. Hervet, I. Théry, J.-L. Renou, F. Fauvelle, and A. Gueiffier (Hetero)arylation of 6-halogenoimidazo[1,2-a]pyridines differently substituted at C(2): influence of the 2-substituent on the Suzuki cross-coupling reaction Helv. Chim. Acta 84 2001 3610 3615
25. K. Billingsley, and S.L. Buchwald Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters J. Am. Chem. Soc. 129 2007 3358 3366 (Pubitemid 46449366)
26. B.U.W. Maes, G.L.F. Lemiere, R. Dommisse, K. Augustyns, and A. Haemers A new approach towards the synthesis of 3-amino-6-(hetero)arylpyridazines based on palladium catalyzed cross-coupling reactions Tetrahedron 56 2000 1777 1781 (Pubitemid 30190446)
27. J. Paeshuyse, L. Coelmont, I. Vliegen, J. Van hemel, J. Vandenkerckhove, E. Peys, B. Sas, E. De Clercq, and J. Neyts Hemin potentiates the anti-hepatitis C virus activity of the antimalarial drug artemisinin Biochem. Biophys. Res. Commun. 348 2006 139 144 (Pubitemid 44177673)
28. J. Paeshuyse, A. Kaul, E. De Clercq, B. Rosenwirth, J.M. Dumont, P. Scalfaro, R. Bartenschlager, and J. Neyts The non-immunosuppressive cyclosporin DEBIO-025 is a potent inhibitor of hepatitis C virus replication in vitro Hepatology 43 2006 761 770