The fight against the influenza A virus H1N1: Synthesis, molecular modeling, and biological evaluation of benzofurazan derivatives as viral RNA polymerase inhibitors

ChemMedChem

Volumn 9, Issue 1, 2014, Pages 129-150

  Pagano, Mafalda ^a   Castagnolo, Daniele ^a   Bernardini, Martina ^a   Fallacara, Anna Lucia ^a,b   Laurenzana, Ilaria ^c   Deodato, Davide ^a   Kessler, Ulrich ^d   Pilger, Beatrice ^d   Stergiou, Lilli ^d   Strunze, Stephan ^d   Tintori, Cristina ^a   Botta, Maurizio ^a,e  

^a UNIVERSITY OF SIENA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c REFERRAL CANCER CENTER OF BASILICATA   (Italy)

^d ETH ZURICH   (Switzerland)

^e TEMPLE UNIVERSITY   (United States)

Author keywords

antiviral agents; benzofurazans; H1N1; influenza A; RNA polymerase

Indexed keywords

1 [1 [4 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLOXY)PHENYL] 1H 1,2,3 TRIAZOL 4 YL] 2,3,4 TRI HYDROXY BETA DEXTRO RIBOFURANOSE; 2 (7 NITROBENZO [C] [1,2,5] OXADIAZOL 4 YLTHIO)ETHYL CINNAMATE; 2 (7 NITROBENZO [C] [1,2,5] OXADIAZOL 4 YLTHIO)ETHYL THIOPHENE 2 CARBOXYLATE; 2 (7 NITROBENZO[C ] [1,2,5] OXADIAZOL 4 YLTHIO)ETHYL 4 BROMOBENZOATE; 3 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLTHIO) N (3 PHENOXYBENZYL)BENZENAMINE; 4 (ALLYLTHIO) 7 NITROBENZO[C] [1,2,5] OXADIAZOLE; 4 [3 (1H IMIDAZOL 1 YL)PHENYLTHIO] 7 NITROBENZO[C] [1,2,5] OXADIAZOLE; 4 [3 [4 (4 METHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL]PHENOXY] 7 NITROBENZO[C] [1,2,5] OXADIAZOLE; 4 [4 (2,5 DIHYDROFURAN 2 YL)PHENOXY] 7 NITROBENZO[C] [1,2,5] OXADIAZOLE; 4 [4 (4 CYCLOHEXENYL 1H 1,2,3 TRIAZOL 1 YL)PHENOXY] 7 NITROBENZO[ C ] [1,2,5] OXA; 4 [4 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLOXY)PHENYL]PIPERAZINE; 4 [4 [4 (4 METHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL]PHENOXY] 7 NITROBENZO[C] [1,2,5] OXADIAZOLE; 4 METHYL N [3 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLTHIO)PHENYLCARBAMOYL]BENZENESULFONAMIDE; 4 NITRO 7 (3 (4 PHENYL 1H 1,2,3 TRIAZOL 1 YL)PHENOXY)BENZO[C] [1,2,5] OXADIAZOLE; 4 NITRO 7 [4 (4 PHENYL 1H 1,2,3 TRIAZOL 1 YL)PHENOXY]BENZO[C] [1,2,5] OXADIAZOLE; 4,6 DICHLORO N [3 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLTHIO)PHENYL] 1,3,5 TRIAZIN 2 AMINE; 4,6 DICHLORO N [3 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLTHIO)PHENYL] 1,3,5 TRIAZIN 2 AMINIUM CHLORIDE; 7 (2 AMINOETHYLTHIO) 4 NITROBENZOFURAZAN; [1 [4 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLOXY)PHENYL] 1H 1,2,3 TRIAZOL 4 YL]METHANOL; ANTIVIRUS AGENT; BENZOFURAZAN DERIVATIVE; METHYL 2 (TERT BUTOXYCARBONYLAMINO) 3 [[1 [4 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLOXY)PHENYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PROPANOATE; N (BIPHENYL 4 YLMETHYL) 3 (7 NITROBENZO[C] [1,2,5] OXA DIAZOL 4 YLTHIO)BENZENAMINE; N (NAPHTHALEN 2 YLMETHYL) 3 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLTHIO)BENZENAMINE; N [2 (7 NITROBENZO[ C] [1,2,5] OXADIAZOL 4 YLTHIO)ETHYL]THIOPHENE 2 CARBOXAMIDE; N [2 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLTHIO)ETHYL]BENZAMIDE; N [2 (7 NITROBENZO[C] [1,2,5] OXADIAZOL 4 YLTHIO)ETHYL]NICOTINAMIDE; N BENZYL 3 (7 NITROBENZO[C ] [1,2,5] OXADIAZOL 4 YLTHIO)BENZENAMINE; RNA DIRECTED RNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BINDING SITE; CYTOTOXICITY; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; INFLUENZA VIRUS A H1N1; MOLECULAR DOCKING; MOLECULAR MODEL; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANTIVIRAL AGENTS; BENZOFURAZANS; H1N1; INFLUENZA A; RNA POLYMERASE;

ANTIVIRAL AGENTS; BENZOXAZOLES; BINDING SITES; DNA-DIRECTED RNA POLYMERASES; ENZYME INHIBITORS; HEK293 CELLS; HUMANS; INFLUENZA A VIRUS, H1N1 SUBTYPE; MOLECULAR DYNAMICS SIMULATION; PROTEIN BINDING; PROTEIN INTERACTION MAPS; PROTEIN STRUCTURE, TERTIARY; PROTEIN SUBUNITS; VIRAL PROTEINS; VIRUS REPLICATION;

EID: 84891744967     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201300378     Document Type: Article

References (42)

1. M. R. Hilleman, Vaccine 2002, 20, 3068-3087.
2. Y. Suzuki, Biol. Pharm. Bull. 2005, 28, 399-408.
3. K. Y. Yuen, S. S. Wong, Hong Kong Med. J. 2005, 11, 189-199.
4. P. Buchy, S. Mardy, S. Vong, T. Toyoda, J. T. Aubin, M. Miller, S. Touch, L. Sovann, J. B. Dufourcq, B. Richner, P. V. Tu, N. T. Tien, W. Lim, J. S. Peiris, S. Van der Werf, J. Clin. Virol. 2007, 39, 164-168.
5. M. Michaelis, H. W. Doerr, J. Cinatl, Jr., Curr. Mol. Med. 2009, 9, 131-151.
6. C. Fraser, C. A. Donnelly, S. Cauchemez, W. P. Hanage, M. D. Van Kerkhove, T. D. Hollingsworth, J. Griffin, R. F. Baggaley, H. E. Jenkins, E. J. Lyons, T. Jombart, W. R. Hinsley, N. C. Grassly, F. Balloux, A. C. Ghani, N. M. Ferguson, A. Rambaut, O. G. Pybus, H. Lopez-Gatell, C. M. Apluche-Aranda, I. B. Chapela, E. P. Zavala, D. M. E. Guevara, F. Checchi, E. Garcia, S. Hugonnet, C. Roth, Science 2009, 324, 1557-1561.
7. F. Carrat, A. Flahault, Vaccine 2007, 25, 6852-6862.
8. J. N. Treanor, N. Engl. J. Med. 2004, 350, 218-220.
9. R. J. Webby, R. G. Webster, Science 2003, 302, 1519-1522.
10. M. Von Itzstein, Nat. Rev. Drug Discovery 2007, 6, 967-974.
11. P. M. Colman, J. Antimicrob. Chemother. 1999, 44, 17-22.
12. P. Ward, I. Small, J. Smith, P. Suter, R. Dutkowski, J. Antimicrob. Chemother. 2005, 55, i 5 -i 21.
13. M. Von Itzstein, W. Y. Wu, G. B. Kok, M. S. Pegg, J. C. Dyason, B. Jin, T. Van Phan, M. L. Smythe, H. F. White, S. W. Oliver, P. M. Colman, J. N. Varghese, D. M. Ryan, J. M. Woods, R. C. Bethell, V. J. Hotham, J. M. Cameron, C. R. Penn, Nature 1993, 363, 418-423.
14. A. J. Hay, A. J. Wolstenholme, J. J. Skehel, M. H. Smith, EMBO J. 1985, 4, 3021-3024.
15. R. G. Douglas, Jr., N. Engl. J. Med. 1990, 322, 443-450.
16. S. M. Wintermeyer, M. C. Nahata, Ann. Pharmacother. 1995, 29, 299-310.
17. P. J. Collins, L. F. Haire, Y. P. Lin, J. Liu, R. J. Russell, P. A. Walker, J. J. Skehel, S. R. Martin, A. J. Hay, S. J. Gamblin, Nature 2008, 453, 1258-1261.
18. M. D. de Jong, T. T. Tran, H. K. Truong, M. H. Vo, G. J. Smith, V. C. Nguyen, V. C. Bach, T. Q. Phan, Q. H. Do, Y. Guan, J. S. Peiris, T. H. Tran, J. Farrar, N. Engl. J. Med. 2005, 353, 2667-2672.
19. A. Moscona, N. Engl. J. Med. 2009, 360, 953-956.
20. R. Salomon, J. Franks, E. A. Govorkova, N. A. Ilyushina, H. L. Yen, D. J. Hulse-Post, J. Humberd, M. Trichet, J. E. Rehg, R. J. Webby, R. G. Webster, E. H. Mann, J. Exp. Med. 2006, 203, 689-697.
21. J. V. Tuttle, M. Tisdale, T. A. Krenitsky, J. Med. Chem. 1993, 36, 119-125.
22. M. Tisdale, M. Ellis, K. Klumpp, S. Court, M. Ford, Antimicrob. Agents Chemother. 1995, 39, 2454-2458.
23. Y. Furuta, K. Takahashi, Y. Fukuda, M. Kuno, T. Kamiyama, K. Kozaki, N. Nomura, H. Egawa, S. Minami, Y. Watanabe, H. Narita, K. Shiraki, Antimicrob. Agents Chemother. 2002, 46, 977-981.
24. K. Takahashi, Y. Furuta, Y. Fukuda, M. Kuno, T. Kamiyama, K. Kozaki, N. Nomura, H. Egawa, S. Minami, K. Shiraki, Antiviral Chem. Chemother. 2003, 14, 235-241.
25. Y. Furuta, K. Takahashi, M. Kuno-Maekawa, H. Sangawa, S. Uehara, K. Kozaki, N. Nomura, H. Egawa, K. Shiraki, Antimicrob. Agents Chemother. 2005, 49, 981-986.
26. J. E. Tomassini, M. E. Davies, J. C. Hastings, R. Lingham, M. Mojena, S. L. Raghoobar, S. B. Singh, J. S. Tkacz, M. A. Goetz, Antimicrob. Agents Chemother. 1996, 40, 1189-1193.
27. U. Kessler, D. Castagnolo, M. Pagano, D. Deodato, M. Bernardini, B. Pilger, C. Ranadheera, M. Botta, Bioorg. Med. Chem. Lett. 2013, 23, 5575-5577.
28. S. Pleschka, R. Jaskunas, O. G. Engelhardt, T. Zurcher, P. Palese, A. Garcia-Sastre, J. Virol. 1996, 70, 4188-4192.
29. D. Castagnolo, M. Pagano, M. Bernardini, M. Botta, Tetrahedron Lett. 2012, 53, 5008-5011.
30. D. Castagnolo, M. Radi, F. Dessì, F. Manetti, M. Saddi, R. Meleddu, A. De Logu, M. Botta, Bioorg. Med. Chem. Lett. 2009, 19, 2203-2205.
31. G. Muratore, L. Goracci, B. Mercorelli, Á. Foeglein, P. Digard, G. Cruciani, G. Palù, A. Loregian, Proc. Natl. Acad. Sci. USA 2012, 109, 6247-6252.
32. G. Muratore, B. Mercorelli, L. Goracci, G. Cruciani, P. Digard, G. Palù, A. Loregian, Antimicrob. Agents Chemother. 2012, 56, 6009-6013.
33. A. L. Hopkins, C. R. Groom, A. Alex, Drug Discovery Today 2004, 9, 430-431.
34. J. A. Wells, C. L. McClendon, Nature 2007, 450, 1001-1009.
35. M. Schmidtke, U. Schnittler, B. Jahn, H. Dahse, A. Stelzner, J. Virol. Methods 2001, 95, 133-143.
36. A. Ghanem, D. Mayer, G. Chase, W. Tegge, R. Frank, G. Kochs, A. García-Sastre, M. Schwemmle, J. Virol. 2007, 81, 7801-7804.
37. K. Wunderlich, D. Mayer, C. Ranadheera, A. S. Holler, B. Mänz, A. Martin, G. Chase, W. Tegge, R. Frank, U. Kessler, M. Schwemmle, PLoS One 2009, 4, e 7517.
38. Maestro version 9.2, Schrödinger LLC, New York, NY (USA), 2011.
39. X. He, J. Zhou, M. Bartlam, R. Zhang, J. Ma, Z. Lou, X. Li, J. Li, A. Joachimiak, Z. Zeng, R. Ge, Z. Rao, Y. Liu, Nature 2008, 454, 1123-1126.
40. E. Obayashi, H. Yoshida, F. Kawai, N. Shibayama, A. Kawaguchi, K. Nagata, J. R. Tame, S. Y. Park, Nature 2008, 454, 1127-1131.
41. Glide version 5.5, Schrödinger Inc., New York, NY, 2009.
42. M. L. Verdonk, J. C. Cole, M. J. Hartshorn, C. W. Murray, R. D. Taylor, Proteins 2003, 52, 609-623.