Novel piperidinylpyrimidine derivatives as inhibitors of HIV-1 LTR activation

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 22, 2008, Pages 9804-9816

  Fujiwara, Norio ^a   Nakajima, Takashi ^a   Ueda, Yutaka ^a   Fujita, Hitoshi ^a   Kawakami, Hajime ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

Anti HIV; HIV 1 LTR; Piperidinylpyrimidine; TNF

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; PIPERIDINYLPYRIMIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; TRANSACTIVATOR PROTEIN; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CYTOKINE PRODUCTION; DRUG SYNTHESIS; FEMALE; GENE ACTIVATION; HUMAN IMMUNODEFICIENCY VIRUS 1; LONG TERMINAL REPEAT; MACROPHAGE ACTIVATION; MOUSE; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-HIV AGENTS; CELLS, CULTURED; HIV LONG TERMINAL REPEAT; HIV-1; HUMANS; INHIBITORY CONCENTRATION 50; JURKAT CELLS; MICE; PYRIMIDINES; TRANSCRIPTIONAL ACTIVATION; TUMOR NECROSIS FACTOR-ALPHA;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 54849415446     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.09.059     Document Type: Article

References (61)

1. Bushman F., Landau N.R., and Emini E.A. Proc Natl. Acad. Sci. U S A. 95 (1998) 11041
2. Cohen O.J., and Fauci A.S. Adv. Intern. Med. 48 (2002) 150
3. Powderly W.G. J. Neurovirol. 6 Suppl. 1 (2000) S8
4. Graham N.M. J. Acquir. Immune Defic. Syndr. 25 Suppl. 1 (2000) S4
5. Moyle G. Clin. Ther. 22 (2000) 911
6. Montessori V., Press N., Harris M., Akagi L., and Montaner J.S.G. CMAJ 170 (2004) 229
7. Clercq E.D. Int. J. Biochem. Cell Biol. 36 (2004) 1800
8. Clercq E.D. J. Med. Chem. 48 (2005) 1297
9. Haseltine W.A. FASEB J. 5 (1991) 2349
10. Cullen B.R. FASEB J. 5 (1991) 2361
11. Jones K.A., and Peterlin B.M. Annu. Rev. Biochem. 63 (1994) 717
12. Pereira L.A., Bentley K., Peeters A., Churchill M.J., and Deacon N.J. Nucleic Acids Res. 28 (2000) 663
13. Li C.J., Dezube B.J., Biswas D.K., Ahlers C.M., and Pardee A.B. Trends Microbiol. 2 (1994) 164
14. Daelemans D., Vandamme A.-M., and De Clerq E. Antiviral Chem. Chemother. 10 (1999) 1
15. Calzad M.A., Macho A., Lucena C., and Muñoz E. Clin. Exp. Immunol. 120 (2000) 317
16. Mitsuhashi S., Kishimoto T., Uraki Y., Okamoto T., and Ubukata M. Bioorg. Med. Chem. 16 (2008) 2645
17. Bedoya L.M., Beltrán M., Sancho R., Olmedo D.A., Sánchez-Palomino S., del Olmo E., López-Pérez J.L., Muñoz E., Feliciano A.S., and Alcamí J. Bioorg. Med. Chem. Lett. 15 (2005) 4447
18. Wang M., Xu Z., Tu P., Yu X., Xiao S., and Yang M. Bioorg. Med. Chem. Lett. 14 (2004) 2585
19. He M., Yuan D., Lin W., Pang R., Yu X., and Yang M. Bioorg. Med. Chem. Lett. 15 (2005) 3978
20. Fujiwara N., Fujita H., Iwai K., Kurimoto A., Shinobu M., and Kawakami H. Bioorg. Med. Chem. Lett. 10 (2000) 1317
21. Denis M., and Ghadirian E. Clin. Exp. Immunol. 97 (1994) 76
22. Maury C.P.J., and Lãhdevirta J. J. Intern. Med. 227 (1990) 253
23. Poli G., Kinter A., Justement J.S., Kehrl J.H., Bressler P., Stanley S., and Fauci A.S. Proc. Natl. Acad. Sci. U.S.A. 87 (1990) 782
24. Fauci A.S. Science 262 (1993) 1011
25. Fauci A.S. Nature 384 (1996) 529
26. Bélec L., Meillet D., Hernvann A., Grésenguet G., and Gherardi R. Clin. Diag. Lab. Immunol. 1 (1994) 117
27. Zangerle R., Reibnegger G., Wachter H., and Fuchs D. AIDS 7 (1993) 175
28. Saha R.N., and Pahan K. J. Neurochem 86 (2003) 1057
29. Brabers N.A.C.H., and Nottet H.S.L.M. Eur. J. Clin. Invest. 36 (2006) 447
30. Pallarés-Trujillo J., López-Soriano F.J., and Argiléas J.M. Med. Res. Rev. 15 (1995) 533
31. Theodore S., Cass W.A., Nath A., Steiner J., Young K., and Maragos W.F. Neurobiol. Dis. 23 (2006) 663
32. Ting P.T., and Koo J.Y. Int. J. Dermatol. 45 (2006) 689
33. Biswas D.K., Dezube B.J., Ahlers C.M., and Pardee A.B. J. Acquir. Immune Defic. Syndr. 6 (1993) 778
34. Smith J.A., Nunnari G., Preuss M., Pomerantz R.J., and Daniel R. Intervirology 50 (2007) 377
35. Makonkawkeyoon S., Limson-Pobre R.N.R., Moreira A.L., Schauf V., and Kaplan G. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 5974
36. Kumar S., Orsini M.J., Lee J.C., McDonnell P.C., Debouck C., and Young P.R. J. Biol. Chem. 271 (1996) 30864
37. Haraguchi S., Day N.K., Kamchaisatian W., Beigier-Pompadre M., Stenger S., Tangsinmankong N., Sleasman J.W., Pizzo S.V., and Cianciolo G.J. AIDS Res. Ther. 3 (2006) 8
38. Baba M., Okamoto M., Kawamura M., Makino M., Higashida T., Takashi T., Kimura Y., Ikeuchi T., Tetsuka T., and Okamoto T. Mol. Pharmacol. 53 (1998) 1097
39. Biswas D.K., Tius M.A., Zhuo J., and Pardee A.B. J. Acquir. Immune Defic. Syndr. Hum. Retrovirol. 12 (1996) 120
40. DeGraw J.I., Kennedy J.G., and Skinner W.A. J. Het. Chem. 3 (1966) 67
41. Rowley M., Collins I., Broughton H.B., Davey W.B., Baker R., Emms F., Marwood R., Patel S., Patel S., Ragan C.I., Freedman S.B., Ball R., and Leeson P.D. J. Med. Chem. 40 (1997) 2374
42. Brooks D.W., Lu L.D.-L., and Masamune S. Angew. Chem., Int. Ed. 18 (1979) 72
43. Krapcho A.P. Synthesis 1982 (1982) 805
44. Robins M.J., and Uzńaski B. Can. J. Chem. 59 (1981) 2608
45. Sugasawa T., Toyoda T., Adachi M., and Sasakura K. J. Am. Chem. Soc. 100 (1978) 4842
46. Carabateas P.M., Surrey A.R., and Harris L.S. J. Med. Chem. 7 (1964) 293
47. Sen R., and Baltimore D. Cell 47 (1986) 921
48. Nabel G., and Baltimore D. Nature 326 (1987) 711
49. Lowenthal J.W., Ballard D.W., Böhnlein E., and Greene W.C. Proc. Natl. Acad. Sci. U.S.A. 86 (1989) 2331
50. Li C.J., Wang C., Friedman D.J., and Pardee A.B. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 5461
51. Fridovich-Keil J.L., Gudas J.M., Dou Q.-P., Bouvard I., and Pardee A.B. Cell Growth Differ. 2 (1991) 67
52. Anzali S., Mederski W.W.K.R., Osswald M., and Dorsch D. Bioorg. Med. Chem. Lett. 8 (1998) 11
53. Mederski W.W.K.R., Osswald M., Dorsch D., Anzali S., Christadler M., Schmitges C.-J., and Wilm C. Bioorg. Med. Chem. Lett. 8 (1998) 17
54. Elguero, J.; Marzin, C.; Katritzky, A. R.; Linda, P. In Adv. Heterocycl. Chem., Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1976, pp 71-210.
55. Brown D.J. In: Weissberger A. (Ed). The Chemistry of Heterocyclic Compounds Vol. 16 (1962), Wiley, New York 227-263
56. Richter S.N., and Palù G. Curr. Med. Chem. 13 (2006) 1305
57. Rusnati M., and Presta M. Drugs Future 27 (2002) 481
58. Hsu M.C., Schutt A.D., Holly M., Slice L.W., Sherman M.I., Richman D.D., Potash M.J., and Volsky D.J. Science 254 (1991) 1799
59. Furia B., Deng L., Wu K., Baylor S., Kehn K., Li H., Donnelly R., Coleman T., and Kashanchi F. J. Biol. Chem. 277 (2002) 4973
60. Biswas D.K., Ahlers C.M., Dezube B.J., and Pardee A.B. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 11044
61. Kunkel S.L., Spengler M., May M.A., Spengler R., Larrick J., and Remick D. J. Biol. Chem. 263 (1988) 5380