Oxoquinoline acyclonucleoside phosphonate analogues as a new class of specific inhibitors of human immunodeficiency virus type 1

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 15, 2012, Pages 5055-5058

  Faro, Letícia V ^a   De Almeida, Jéssica M ^a   Cirne Santos, Cláudio C ^a,b   Giongo, Viveca A ^a   Castello Branco, Luís R ^b   Oliveira, Ingrid De B ^a   Barbosa, Juliana E F ^a   Cunha, Anna C ^a   Ferreira, Vítor F ^a   De Souza, Marcos C ^a   Paixão, Izabel C N P ^a   De Souza, Maria Cecília B V ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b INSTITUTO OSWALDO CRUZ   (Brazil)

Author keywords

Acyclonucleoside phosphonate; Anti HIV 1; Antiviral; Oxoquinoline

Indexed keywords

ACYCLIC NUCLEOSIDE; ANTIRETROVIRUS AGENT; ETHYL 1 [(DIISOPROPOXYPHOSPHORYL)METHYL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; NONHUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; VIRUS INHIBITION;

ANTI-HIV AGENTS; HIV-1; HUMANS; NUCLEOSIDES; PHOSPHOROUS ACIDS; QUINOLONES; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 84863987507     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.06.020     Document Type: Article

References (54)

1. F. Barré-Sinoussi, J.C. Chermann, F. Rey, M.T. Nugeyre, S. Chamaret, J. Gruest, C. Dauguet, C. Axler-Blin, F. Vezinet-Brun, C. Rouzioux, W. Rozenbaum, and L. Montagnier Science 220 1983 868
2. D. Zagury, J. Bernard, J. Leibowitch, B. Safai, J.E. Groopman, M. Feldman, M.G. Sarngadharan, and R.C. Gallo Science 226 1984 449
3. A. Carr Nat. Rev. Drug Discovery 2 2003 624
4. J. Martinez-Picado, M.P. De Pasquale, N. Kartsonis, G.J. Hanna, G. Wong, D. Finzi, E. Rosemberg, H.F. Gunthard, L. Sutton, A. Sarava, C.J. Petropoulos, N. Hellmann, B.D. Walker, D.D. Richman, R. Siliciano, and R.T. DÁquila Proc. Natl. Acad. Sci. U.S.A. 97 2000 10848
5. L.R. Boone, and G.W. Koszalka Curr. Opin. Invest. Drugs 11 2010 863
6. A. Ahmeda, and M. Daneshtalaba J. Pharm. Sci. 15 2012 52
7. A. Saleh, J. Friesen, S. Baumeister, U. Gross, and W. Bohne Antimicrob. Agents Chemother. 51 2007 1217
8. C.H. Park, J. Lee, H.Y. Jung, M.J. Kim, S.H. Lim, H.T. Yeo, E.C. Choi, E.J. Yoon, K.W. Kim, J.H. Cha, S.H. Kim, D.J. Chang, D.Y. Kwona, F. Li, and Y.G. Suh Bioorg. Med. Chem. 15 2007 6517
9. M. Hadjeri, E.V. Peiller, C. Beney, N. Deka, M.A. Lawson, C. Dumontet, and A. Boumendjel J. Med. Chem. 47 2004 4964
10. M. Baba, M. Okamoto, M. Makino, Y. Kimura, T. Ikeuchi, T. Sakaguchi, and T. Okamoto Antimicrob. Agents Chemother. 41 1997 1250
11. M. Baba, M. Okamoto, M. Kawamura, M. Makino, T. Higashida, T. Takashi, Y. Kimura, T. Ikeuchi, T. Tetsuka, and T. Okamoto Mol. Pharmacol. 53 1998 1097
12. V. Cecchetti, C. Parolin, S. Moro, T. Pecere, E. Filipponi, A. Calistri, O. Tabarrini, B. Gatto, M. Palumbo, A. Fravolini, and G. Palu' J. Med. Chem. 43 2000 3799
13. K. Yusa, and S. Harada Curr. Pharm. Des. 10 2004 4055
14. O. Tabarrini, M. Stevens, V. Cecchetti, S. Sabatini, M. Dell'Uomo, G. Manfroni, M. Palumbo, C. Pannecouque, E. De Clercq, and A. Fravolini J. Med. Chem. 47 2004 5567
15. S. Richter, C. Parolin, B. Gatto, C. Del Vecchio, E. Brocca-Cofano, A. Fravolini, G. Palù, and M. Palumbo Antimicrob. Agents Chemother. 2004 1895 48
16. S.N. Richter, B. Gatto, O. Tabarrini, A. Fravolini, and M. Palumbo Bioorg. Med. Chem. Lett. 15 2005 4247
17. M. Stevens, J. Balzarini, O. Tabarrini, G. Andrei, R. Snoeck, V. Cecchetti, A. Fravolini, E. De Clercq, and C.J. Pannecouque Antimicrob. Chem. 56 2005 847
18. M. Sato, T. Motomura, H. Aramaki, T. Matsuda, M. Yamashita, Y. Ito, H. Kawakami, Y. Matsuzaki, W. Watanabe, K. Yamataka, S. Ikeda, E. Kodama, M. Matsuoka, and H. Shinkai J. Med. Chem. 49 2006 1506
19. M. Stevens, M. Pollicita, C. Pannecouque, E. Verbeken, O. Tabarrini, V. Cecchetti, S. Aquaro, C.F. Perno, A. Fravolini, E. De Clercq, D. Schols, and J. Balzarini Antimicrob. Agents Chemother. 51 2007 1407
20. R. Dayam, L.Q. Al-Mawsawi, Z. Zawahir, M. Witvrouw, Z. Debyser, and N. Neamati J. Med. Chem. 51 2008 1136
21. S. Massari, D. Daelemans, G. Manfroni, S. Sabatini, O. Tabarrini, C. Pannecouque, and V. Cecchetti Bioorg. Med. Chem. 17 2009 667
22. Z.G. Luo, J.J. Tan, Y. Zeng, C.X. Wang, and L.M. Hu Mini-Reviews Med. Chem. 10 2010 1046
23. Barney, R. J. Ph.D. Thesis, University of Iowa, 2010.
24. E. De Clercq Collect. Czech. Chem. Commun. 76 2011 829
25. E. De Clercq, and A. Holý Nature 4 2005 928
26. E. De Clercq Antiviral Res. 75 2007 1
27. C. Callebaut, K. Stray, L. Tsai, M. Williams, Z. Yang, C. Cannizzaro, S.A. Leavitt, X. Liu, K. Wang, B.P. Murray, A. Mulato, M. Hatada, T. Priskich, N. Parkin, S. Swaminathan, W. Lee, and G. He Antimicrob. Agents Chemother. 55 2011 1366
28. H.B. Maruyama, M. Aisawa, and T. Sawada Antimicrob. Agents Chemother. 16 1979 444
29. F.E. Hahn Naturwissenschaften 68 1981 90
30. T.A. Guise Cancer Treat Rev. 34 2008 S19
31. M.B. Martin, J.S. Grimley, J.C. Lewis, H.T. Heath, B.N. Bailey, H. Kendrick, V. Yardley, A. Caldera, R. Lira, J.A. Urbina, S.N. Moreno, R. Docampo, S.L. Croft, and E. Oldfield J. Med. Chem. 44 2001 909
32. V. Yardley, A.A. Khan, M.B. Martin, T.R. Slifer, F.G. Aruajo, S.N. Moreno, R. Docampo, S.L. Croft, and E. Oldfield Antimicrob. Agents Chemother. 46 2002 929
33. C.M. Shipman, M.J. Rogers, J.F. Apperley, R. Graham, G. Russell, and P.I. Croucher Br. J. Haematol. 98 1997 665
34. V. Kunzmann, E. Bauer, J. Feurle, F. Weissinger, H.P. Tony, and M. Wilhelm Blood 96 2000 384
35. J.M. Sanders, S. Ghosh, J.M. Chan, G. Meints, H. Wang, A.M. Raker, Y. Song, A. Colantino, A. Burzynska, P. Kafarski, C.T. Morita, and E. Oldfield J. Med. Chem. 47 2004 375
36. C.V.B.S. Canuto, C.R.B. Gomes, I.P. Marques, L.V. Faro, F.C. Santos, I.C.P.P. Frugulhetti, T.M.L. Souza, A.C. Cunha, G.A. Romeiro, V.F. Ferreira, and M.C.B.V. Souza Lett. Drug Des. Discovery 4 2007 404
37. B.D. Lucero, C.R.B. Gomes, I.C.P.P. Frugulhetti, L.V. Faro, L. Alvarenga, M.C.B.V. Souza, T.M.L. Souza, and V.F. Ferreira Bioorg. Med. Chem. Lett. 16 2006 1010
38. T.S. Torres, W.P. de Macedo, L.F. Pedrosa, M.C.B.V. de Souza, V.F. Ferreira, A.C. Cunha, T. Fogel, F.C. Santos, I.P. Marques, I.C.P. Paixão, and M.C. de Souza Lett. Drug Des. Discovery 5 2008 644
39. P.A. Abreu, V.A. da Silva, F.C. Santos, H.C. Castro, C.S. Riscado, M.T. de Souza, C.P. Ribeiro, J.E. Barbosa, C.C. dos Santos, C.R. Rodrigues, V. Lione, B.A. Correa, A.C. Cunha, V.F. Ferreira, M.C. de Souza, and I.C.P. Paixão Curr. Microbiol. 62 2011 1349
40. T.M. Souza, C.C. Cirne-Santos, D.Q. Rodrigues, C.M. Abreu, A. Tanuri, V.F. Ferreira, I.P. Marques, M.C. de Souza, C.F. Fontes, I.C. Frugulhetti, and D.C. Bou-Habib Curr. HIV Res. 6 2008 209
41. F.C. Santos, P. Abreu, H.C. Castro, I.C.P.P. Paixão, C.C. Cirne-Santos, V. Giongo, J.E. Barbosa, B.R. Simonetti, V. Garrido, D.C. Bou-Habib, D.O. Silva, P.N. Batalha, J.R. Temerozo, T.M. Souza, C.M. Nogueira, A.C. Cunha, C.R. Rodrigues, V.F. Ferreira, and M.C.B.V. Souza Bioorg. Med. Chem. 17 2009 5476
42. G.F. Deffin, and J.D. Kendall J. Am. Chem. Soc. 70 1948 893
43. H.R. Snyder, H.E. Freier, P. Kovacic, and E.M.V. Heyningen J. Am. Chem. Soc. 69 1947 371
44. W.M. Lauer, R.T. Arnold, B. Tiffany, and H. Tinker J. Am. Chem. Soc. 68 1946 1268
45. V.G. Ramsey, and L.H. Cretcher J. Am. Chem. Soc. 69 1947 1659
46. C.C. Price, H.R. Snyder, O.H. Bullitt Jr., and P. Kovacic J. Am. Chem. Soc. 69 1947 374
47. B. Riegel, G.R. Lappin, B.H. Adelson, R.I. Jackson, C.J. Albisetti Jr., R.M. Dodson, and R.H. Baker J. Am. Chem. Soc. 68 1946 1264
48. R.B. Roberts J. Am. Chem. Soc. 70 1948 277
49. J.M. Ruxer, C. Lachoux, J.B. Ousset, J.L. Torregrosa, and G.J. Mattioda Heterocycl. Chem. 31 1994 409
50. Lesher, G.Y.; Schodack, N. K. U.S. Patent 3, 313, 818, 1967.
51. L.M. Schultze, H.H. Chapman, N.J.P. Dubree, R.J. Jones, K.M. Kent, T.T. Lee, M.S. Louie, M.J. Postich, E.J. Prisbe, J.C. Rohloff, and R.H. Yu Tetrahedron Lett. 1998 1853 39
52. C.C. Cirne-Santos, V.L. Teixeira, L.R. Castello-Branco, I.C. Frugulhetti, and D.C. Bou-Habib Planta Med. 72 2006 295
53. R. Filler, and R. Saha Future Med. Chem. 1 2009 777
54. L. Hunter, and J. Beilstein Org. Chem. 6 2010 1