Efficient synthesis and anti-enteroviral activity of 9-arylpurines

European Journal of Medicinal Chemistry

Volumn 49, Issue , 2012, Pages 279-288

  Aguado, Leire ^a   Canela, María Dolores ^a   Thibaut, Hendrik Jan ^b   Priego, Eva María ^a   Camarasa, María José ^a   Leyssen, Pieter ^b   Neyts, Johan ^b   Pérez Pérez, María Jesús ^b  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Coxsackie virus B3; Enterovirus; Microwave assisted synthesis; Oxazolidinone; Purines

Indexed keywords

2 ((3 (6 ETHOXY 9H PURIN 9 YL)PHENYL)AMINO)ETHANOL; 3 (3 ((5 AMINO 6 CHLORO 2 METHYLPYRIMIDIN 4 YL)AMINO)PHENYL)OXAZOLIDIN 2 ONE; 3 (3 ((5 AMINO 6 CHLOROPYRIMIDIN 4 YL)AMINO)PHENYL)OXAZOLIDIN 2 ONE; 3 (3 (6 CHLORO 2 METHYL 8 OXO 7H PURIN 9(8H) YL)PHENYL)OXAZOLIDIN 2 ONE; 3 (3 (6 CHLORO 2 METHYL 9H PURIN 9 YL)PHENYL)OXAZOLIDIN 2 ONE; 3 (3 (6 CHLORO 8 OXO 7H PURIN 9(8H) YL)PHENYL)OXAZOLIDIN 2 ONE; 3 (3 (6 CHLORO 8 OXO 7H PURIN 9(8H)YL)PHENYL)OXAZOLIDIN 2 ONE; 3 (3 (6 CHLORO 9H PURIN 9 YL)PHENYL)OXAZOLIDIN 2 ONE; 6 CHLORO 2 METHYL 9 [3 (N,N DIMETHYLAMINO)PHENYL]PURIN 8 ONE; 6 CHLORO 9 (3 (N,N DIMETHYLAMINO)PHENYL) 2 METHYL 9H PURIN 8 YL ETHYL CARBONATE; 6 CHLORO 9 (3 (N,N DIMETHYLAMINO)PHENYL) 2 METHYL 9H PURIN 8 YL PHENYL CARBONATE; 6 CHLORO 9 (3 (N,N DIMETHYLAMINO)PHENYL) 2,7 DIMETHYL 7H PURIN 8(9H) ONE; 6 CHLORO 9 [3 (N,N DIMETHYLAMINO)PHENYL] 2 METHYLPURINE; 6 CHLORO 9 [3 (N,N DIMETHYLAMINO)PHENYL]PURIN 8 ONE; 6 CHLORO 9 [3E(N,N DIMETHYLAMINO)PHENYL]PURINE; 6 CHLORO 9 [4 (N,N DIMETHYLAMINO)PHENYL] 2 METHYLPURINE; ANTIVIRUS AGENT; ENVIROXIME; N (3 ((5 AMINO 6 CHLORO 2 METHYLPYRIMIDIN 4 YL)AMINO)PHENYL)ACETAMIDE; N (3 ((5 AMINO 6 CHLOROPYRIMIDIN 4 YL)AMINO)PHENYL)ACETAMIDE; N (3 (2 OXOOXAZOLIDIN 3 YL)PHENYL)ACETAMIDE; N (3 (6 CHLORO 2 METHYL 9H PURIN 9 YL)PHENYL) N METHYLACETAMIDE; N (3 (6 CHLORO 2 METHYL 9H PURIN 9 YL)PHENYL)ACETAMIDE; N (3 (6 CHLORO 2 METHYL 9H PURIN 9 YL)PHENYL)N (CYCLOPROPYLMETHYL)ACETAMIDE; N (3 (6 CHLORO 2 METHYL 9H PURIN 9 YL)PHENYL)N ETHYLACETAMIDE; N (3 (6 CHLORO 9H PURIN 9 YL)PHENYL) N METHYLACETAMIDE; N (3 (6 CHLORO 9H PURIN 9 YL)PHENYL)ACETAMIDE; OXAZOLIDINONE DERIVATIVE; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; COXSACKIE VIRUS B3; COXSACKIE VIRUS B4; CROSS RESISTANCE; CYTOTOXICITY; DRUG SYNTHESIS; ECHO VIRUS; HUMAN; HUMAN CELL; NONHUMAN; STRUCTURE ACTIVITY RELATION; VERO CELL; VIRUS REPLICATION;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; CERCOPITHECUS AETHIOPS; ENTEROVIRUS B, HUMAN; ENTEROVIRUS INFECTIONS; HALOGENATION; HUMANS; MICROBIAL SENSITIVITY TESTS; MICROWAVES; MODELS, MOLECULAR; OXAZOLIDINONES; PURINES; VERO CELLS;

EID: 84857234397     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.01.022     Document Type: Article

References (24)

1. M.H. Sawyer Semin. Pediatr. Infect. Dis. 13 2002 40 47
2. C. Kawai Circulation 99 1999 1091 1100
3. K.U. Knowlton CVB infection and mechanisms of viral cardiomyopathy Group B Coxsackieviruses 2008 315 335
4. A.M. De Palma, I. Vliegen, E. De Clercq, and J. Neyts Med. Res. Rev. 28 2008 823 884
5. K.M. Drescher, and S.M. Tracy The CVB and etiology of type 1 diabetes Group B Coxsackieviruses 2008 259 274
6. S. Huber, and A.I. Ramsingh Viral Immunol. 17 2004 358 369
7. A.M. De Palma, W. Heggermont, K. Lanke, B. Coutard, M. Bergmann, A.M. Monforte, B. Canard, E. De Clercq, A. Chimirri, G. Purstinger, J. Rohayem, F. van Kuppeveld, and J. Neyts J. Virol. 82 2008 4720 4730
8. M.P. Langford, W.A. Ball, and J.P. Ganley Antivir. Res. 27 1995 355 365
9. A.M. De Palma, H.J. Thibaut, L. van der Linden, K. Lanke, W. Heggermont, S. Ireland, R. Andrews, M. Arimilli, T.H. Al-Tel, E. De Clercq, F. van Kuppeveld, and J. Neyts Antimicrob. Agents Chemother. 53 2009 1850 1857
10. B.A. Heinz, and L.M. Vance J. Virol. 69 1995 4189 4197
11. L. Aguado, H.J. Thibaut, E.M. Priego, M.L. Jimeno, M.J. Camarasa, J. Neyts, and M.J. Pérez-Pérez J. Med. Chem. 53 2010 316 324
12. C.L. Cooper Clin. Infect. Dis. 41 2005 S69 S72
13. H.J. Thibaut, P. Leyssen, G. Puerstinger, A. Muigg, J. Neyts, and A.M. De Palma Antivir. Res. 90 2011 213 217
14. M. Sala, A.M. De Palma, H. Hrebabecky, R. Nencka, M. Dracinsky, P. Leyssen, J. Neyts, and A. Holy Bioorg. Med. Chem. 18 2010 4374 4384
15. L. Aguado, M.J. Camarasa, and M.J. Pérez-Pérez J. Comb. Chem. 11 2009 210 212
16. M. Graupe, R.L. Halcomb, WO2009005687A1, (2009).
17. L.-L. Gundersen, M. Braendvang, US20070203159A1, (2007).
18. S. Ueda, and H. Nagasawa J. Org. Chem. 74 2009 4272 4277
19. A.B. Cooper, US2009118284, (2009).
20. T. Taniguchi, N. Goto, and H. Ishibashi Tetrahedron Lett. 50 2009 4857 4858
21. H.J. Thibaut, L. van der Linden, J. Paeshuyse, A. De Palma, L. Aguado, F. Van Kuppeveld, M.J. Pérez-Pérez, and J. Neyts Antivir. Res. 86 2010 A27-A27
22. M.J.T. Frisch, G. W., H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr. , T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G.Cioslowski, J.Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., Pople, J. A, (2004).
23. W. Rocchia, S. Sridharan, A. Nicholls, E. Alexov, A. Chiabrera, and B. Honig J. Comput. Chem. 23 2002 128 137
24. W. Rocchia, E. Alexov, and B. Honig J. Phys. Chem. B. 105 2001 6507 6514