Design, synthesis, and biological evaluation of 1,3-diarylpropenones as dual inhibitors of HIV-1 reverse transcriptase

ChemMedChem

Volumn 9, Issue 8, 2014, Pages 1869-1879

  Meleddu, Rita ^a   Cannas, Valeria ^a   Distinto, Simona ^a   Sarais, Giorgia ^a   Del Vecchio, Claudia ^b   Esposito, Francesca ^a   Bianco, Giulia ^a   Corona, Angela ^a   Cottiglia, Filippo ^a   Alcaro, Stefano ^c   Parolin, Cristina ^b   Artese, Anna ^c   Scalise, Daniela ^c   Fresta, Massimo ^c   Arridu, Antonella ^a   Ortuso, Francesco ^c   Maccioni, Elias ^a   Tramontano, Enzo ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

^c UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

Author keywords

antiviral agents; dual inhibitors; enzymes; HIV 1; molecular modeling; RNase H

Indexed keywords

1 (3 NITROPHENYL) 3 (1 METHOXYNAPHTHALEN 2 YL)PROP 2 EN 1 ONE; 1 (4 BIPHENYL) 3 (1 METHOXYNAPHTHALEN 2 YL)PROP 2 EN 1 ONE; 1 (4 CHLOROPHENYL) 3 (1 METHOXYNAPHTHALEN 2 YL)PROP 2 EN -ONE; 1 (4 FLUOROPHENYL) 3 (1 METHOXYNAPHTHALEN 2 YL)PROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 (1 METHOXYNAPHTHALEN 2 YLPROP 2 EN 1 ONE; DNA POLYMERASE; EFAVIRENZ; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; RIBONUCLEASE H; UNCLASSIFIED DRUG; ALKENE; PROPYLENE; REVERSE TRANSCRIPTASE, HUMAN IMMUNODEFICIENCY VIRUS 1; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ANTIVIRAL ACTIVITY; ARTICLE; BLOOD BRAIN BARRIER; CHEMICAL ANALYSIS; COMPUTER MODEL; CONTROLLED STUDY; CYTOTOXICITY; DRUG ADSORPTION; DRUG BINDING; DRUG DESIGN; DRUG EFFICACY; DRUG PENETRATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INHIBITION; IN VITRO STUDY; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MUTATION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMISTRY; DRUG EFFECTS; HEK293 CELL LINE; HUMAN; KINETICS; METABOLISM; PROTEIN TERTIARY STRUCTURE; SYNTHESIS;

ALKENES; BINDING SITES; DRUG DESIGN; HEK293 CELLS; HIV REVERSE TRANSCRIPTASE; HUMANS; KINETICS; MOLECULAR DOCKING SIMULATION; PROTEIN STRUCTURE, TERTIARY; REVERSE TRANSCRIPTASE INHIBITORS; RIBONUCLEASE H;

EID: 84905216702     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201402015     Document Type: Article

References (63)

1. P. Zhan, X. Liu, Z. Li, C. Pannecouque, E. De Clercq, Curr. Med. Chem. 2009, 16, 3903-3917
2. R. Morphy, Z. Rankovic, J. Med. Chem. 2005, 48, 6523-6543.
3. B. L. Roth, D. J. Sheffler, W. K. Kroeze, Nat. Rev. Drug Discovery 2004, 3, 353-359.
4. Y. Mehellou, E. De Clercq, J. Med. Chem. 2010, 53, 521-538.
5. G. N. Nikolenko, S. Palmer, F. Maldarelli, J. W. Mellors, J. M. Coffin, V. K. Pathak, Proc. Natl. Acad. Sci. USA 2005, 102, 2093-2098.
6. F. Esposito, A. Corona, E. Tramontano, Mol. Biol. Int. 2012, 586401.
7. O. Schatz, F. V. Cromme, F. Grüninger-Leitch, S. F. J. Le Grice, FEBS Lett. 1989, 257, 311-314.
8. K. Klumpp, T. Mirzadegan, Curr. Pharm. Des. 2006, 12, 1909-1922
9. E. Tramontano, Mini-Rev. Med. Chem. 2006, 6, 727-737
10. E. Tramontano, R. Di Santo, Curr. Med. Chem. 2010, 17, 2837-2853
11. S. Distinto, E. Maccioni, R. Meleddu, A. Corona, S. Alcaro, E. Tramontano, Curr. Pharm. Des. 2013, 19, 1850-1859.
12. J. Q. Hang, S. Rajendran, Y. Yang, Y. Li, P. W. K. In, H. Overton, K. E. B. Parkes, N. Cammack, J. A. Martin, K. Klumpp, Biochem. Biophys. Res. Commun. 2004, 317, 321-329
13. E. Tramontano, F. Esposito, R. Badas, R. Di Santo, R. Costi, P. La Colla, Antiviral Res. 2005, 65, 117-124
14. D. M. Himmel, K. A. Maegley, T. A. Pauly, J. D. Bauman, K. Das, C. Dharia, A. D. Clark, Jr., K. Ryan, M. J. Hickey, R. A. Love, S. H. Hughes, S. Bergqvist, E. Arnold, Structure 2009, 17, 1625-1635
15. T. A. Kirschberg, M. Balakrishnan, N. H. Squires, T. Barnes, K. M. Brendza, X. Chen, E. J. Eisenberg, W. Jin, N. Kutty, S. Leavitt, A. Liclican, Q. Liu, X. Liu, J. Mak, J. K. Perry, M. Wang, W. J. Watkins, E. B. Lansdon, J. Med. Chem. 2009, 52, 5781-5784
16. H.-P. Su, Y. Yan, G. S. Prasad, R. F. Smith, C. L. Daniels, P. D. Abeywickrema, J. C. Reid, H. M. Loughran, M. Kornienko, S. Sharma, J. A. Grobler, B. Xu, V. Sardana, T. J. Allison, P. D. Williams, P. L. Darke, D. J. Hazuda, S. Munshi, J. Virol. 2010, 84, 7625-7633
17. S. Chung, D. M. Himmel, J.-K. Jiang, K. Wojtak, J. D. Bauman, J. W. Rausch, J. A. Wilson, J. A. Beutler, C. J. Thomas, E. Arnold, S. F. J. Le Grice, J. Med. Chem. 2011, 54, 4462-4473
18. E. B. Lansdon, Q. Liu, S. A. Leavitt, M. Balakrishnan, J. K. Perry, C. Lancaster-Moyer, N. Kutty, X. Liu, N. H. Squires, W. J. Watkins, T. A. Kirschberg, Antimicrob. Agents Chemother. 2011, 55, 2905-2915
19. V. Suchaud, F. Bailly, C. Lion, E. Tramontano, F. Esposito, A. Corona, F. Christ, Z. Debyser, P. Cotelle, Bioorg. Med. Chem. Lett. 2012, 22, 3988-3992.
20. D. M. Himmel, S. G. Sarafianos, S. Dharmasena, M. M. Hossain, K. McCoy-Simandle, T. Ilina, A. D. Clark, J. L. Knight, J. G. Julias, P. K. Clark, K. Krogh-Jespersen, R. M. Levy, S. H. Hughes, M. A. Parniak, E. Arnold, ACS Chem. Biol. 2006, 1, 702-712.
21. T. Kharlamova, F. Esposito, L. Zinzula, G. Floris, Y.-C. Cheng, G. Dutschman, E. Tramontano, Med. Chem. 2009, 5, 398-410
22. E. Tramontano, T. Kharlamova, L. Zinzula, F. Esposito, J. Chemother. 2011, 23, 273-276
23. F. Esposito, T. Kharlamova, S. Distinto, L. Zinzula, Y.-C. Cheng, G. Dutschman, G. Floris, P. Markt, A. Corona, E. Tramontano, FEBS J. 2011, 278, 1444-1457.
24. F. Esposito, A. Corona, L. Zinzula, T. Kharlamova, E. Tramontano, Chemotherapy 2012, 58, 299-307.
25. S. Distinto, F. Esposito, J. Kirchmair, M. C. Cardia, M. Gaspari, E. Maccioni, S. Alcaro, P. Markt, G. Wolber, L. Zinzula, E. Tramontano, Eur. J. Med. Chem. 2012, 50, 216-229.
26. L. M. A. Lima, E. J. Barreiro, Curr. Med. Chem. 2005, 12, 23-49.
27. H. Pelemans, R. Esnouf, E. De Clercq, J. Balzarini, Mol. Pharmacol. 2000, 57, 954-960.
28. T. Rosen, A. A. Nagel, J. P. Rizzi, J. L. Ives, J. B. Daffeh, A. H. Ganong, K. Guarino, J. Heym, S. McLean, J. Med. Chem. 1990, 33, 2715-2720.
29. T. Yonetani, Methods Enzymol. 1982, 87, 500-509.
30. A. K. Felts, K. LaBarge, J. D. Bauman, D. V. Patel, D. M. Himmel, E. Arnold, M. A. Parniak, R. M. Levy, J. Chem. Inf. Model. 2011, 51, 1986-1998.
31. S.-Y. Huang, X. Zou, Proteins: Struct. Funct. Bioinf. 2007, 66, 399-421.
32. K. A. Paris, O. Haq, A. K. Felts, K. Das, E. Arnold, R. M. Levy, J. Med. Chem. 2009, 52, 6413-6420.
33. H. M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T. N. Bhat, H. Weissig, I. N. Shindyalov, P. E. Bourne, Nucleic Acids Res. 2000, 28, 235-242.
34. Schrödinger LLC, "QM Polarized Protocol" in Schrödinger Suite, New York, NY, USA.
35. J. Y. Chung, J.-M. Hah, A. E. Cho, J. Chem. Inf. Model. 2009, 49, 2382-2387.
36. P. A. Kollman, I. Massova, C. Reyes, B. Kuhn, S. Huo, L. Chong, M. Lee, T. Lee, Y. Duan, W. Wang, O. Donini, P. Cieplak, J. Srinivasan, D. A. Case, T. E. Cheatham, Acc. Chem. Res. 2000, 33, 889-897.
37. J. D. Pata, W. G. Stirtan, S. W. Goldstein, T. A. Steitz, Proc. Natl. Acad. Sci. USA 2004, 101, 10548-10553.
38. J. S. Ren, R. Esnouf, E. Garman, D. Somers, C. Ross, I. Kirby, J. Keeling, G. Darby, Y. Jones, D. Stuart, D. Stammers, Nat. Struct. Biol. 1995, 2, 293-302.
39. K. Das, J. D. Bauman, A. D. Clark, Y. V. Frenkel, P. J. Lewi, A. J. Shatkin, S. H. Hughes, E. Arnold, Proc. Natl. Acad. Sci. USA 2008, 105, 1466-1471.
40. J. S. Ren, C. Nichols, L. E. Bird, T. Fujiwara, H. Sugimoto, D. I. Stuart, D. K. Stammers, J. Biol. Chem. 2000, 275, 14316-14320.
41. K. Das, J. D. Bauman, A. S. Rim, C. Dharia, A. D. Clark, M.-J. Camarasa, J. Balzarini, E. Arnold, J. Med. Chem. 2011, 54, 2727-2737.
42. K. J. Bowers, E. Chow, H. Xu, R. O. Dror, M. P. Eastwood, B. A. Gregersen, J. L. Klepeis, I. Kolossvary, M. A. Moraes, F. D. Sacerdoti, J. K. Salmon, Y. Shan, D. E. Shaw in Proceedings SC06 ACM/IEEE Conference, Tampa, FL (USA), 2006, p. 84.
43. Q. Gong, L. Menon, T. Ilina, L. G. Miller, J. Ahn, M. A. Parniak, R. Ishima, Chem. Biol. Drug Des. 2011, 77, 39-47.
44. J. M. Seckler, M. D. Barkley, P. L. Wintrode, Biophys. J. 2011, 100, 144-153
45. T. Ilina, K. LaBarge, S. G. Sarafianos, R. Ishima, M. A. Parniak, Biology 2012, 1, 521-541.
46. C. Celia, D. Cosco, D. Paolino, M. Fresta, Med. Res. Rev. 2011, 31, 716-756.
47. E. Tramontano, Y. c. Cheng, Biochem. Pharmacol. 1992, 43, 1371-1376
48. J. W. Mellors, G. J. Im, E. Tramontano, S. R. Winkler, D. J. Medina, G. E. Dutschman, H. Z. Bazmi, G. Piras, C. J. Gonzalez, Y. C. Cheng, Mol. Pharmacol. 1993, 43, 11-16.
49. C. Parolin, B. Gatto, C. Del Vecchio, T. Pecere, E. Tramontano, V. Cecchetti, A. Fravolini, S. Masiero, M. Palumbo, G. Palù, Antimicrob. Agents Chemother. 2003, 47, 889-896.
50. Schrödinger LLC, Maestro GUI, New York, NY, USA, 2012.
51. T. Halgren, J. Comput. Chem. 1996, 17, 520-552.
52. W. Hasel, T. F. Hendrickson, W. C. Still, Tetrahedron Comput. Methodol. 1988, 1, 103-116.
53. G. A. Kaminski, R. A. Friesner, J. Tirado-Rives, W. L. Jorgensen, J. Phys. Chem. B 2001, 105, 6474-6487.
54. K. J. Bowers, R. O. Dror, D. E. Shaw, J. Chem. Phys. 2006, 124, 184109-184111.
55. W. L. Jorgensen, J. Chandrasekhar, J. D. Madura, R. W. Impey, M. L. Klein, J. Chem. Phys. 1983, 79, 926-935.
56. G. J. Martyna, D. J. Tobias, M. L. Klein, J. Chem. Phys. 1994, 101, 4177-4189.
57. D. A. Gibson, E. A. Carter, J. Phys. Chem. 1993, 97, 13429-13434.
58. J.-P. Ryckaert, G. Ciccotti, H. Berendsen, J. Comp. Physiol. 1977, 23, 327-341.
59. T. Darden, D. York, L. Pedersen, J. Chem. Phys. 1993, 98, 10089-10092.
60. InteLigand Software GmbH, LigandScout 3.0, Maria Enzersdorf, Austria, 2009
61. G. Wolber, T. Langer, J. Chem. Inf. Model. 2005, 45, 160-169.
62. W. Humphrey, A. Dalke, K. Schulten, J. Mol. Graphics 1996, 14, 33-38.
63. G. Cavallaro, M. Fresta, G. Giammona, G. Puglisi, A. Villari, Int. J. Pharm. 1994, 111, 31-41.