1-[2-(2-Benzoyl- and 2-benzylphenoxy)ethyluracils as potent anti-HIV-1 agents

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 19, 2011, Pages 5794-5802

  Novikov, Mikhail S ^a   Ivanova, Olga N ^b   Ivanov, Alexander V ^b   Ozerov, Alexander A ^a   Valuev Elliston, Vladimir T ^b   Temburnikar, Kartik ^d   Gurskaya, Galina V ^b   Kochetkov, Sergey N ^b   Pannecouque, Christophe ^c   Balzarini, Jan ^c   Seley Radtke, Katherine L ^d  

^a VOLGOGRAD STATE MEDICAL UNIVERSITY   (Russian Federation)

^b ENGELHARDT INSTITUTE OF MOLECULAR BIOLOGY   (Russian Federation)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^d UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

Benzophenone; HIV 1; Non nucleoside reverse transcriptase inhibitors; Reverse transcriptase; Uracil

Indexed keywords

1 [2 (2 BENZOYL 4 BROMOPHENOXY)ETHYL]URACIL; 1 [2 (2 BENZOYL 4 CHLOROPHENOXY)ETHYL]URACIL; 1 [2 (2 BENZOYL 4 FLUOROPHENOXY)ETHYL]URACIL; 1 [2 (2 BENZOYL 4 METHYLPHENOXY)ETHYL]URACIL; 1 [2 (2 BENZOYL)ETHYL]URACIL DERIVATIVE; 1 [2 (2 BENZOYLPHENOXY)ETHYL]URACIL DERIVATIVE; 1 [2 (2 BENZYL 4 METHYLPHENOXY)ETHYL]URACIL; 1 [2 [2 (3 METHYLBENZYL) 4 METHYLPHENOXY]ETHYL]URACIL; 1 [2 [2 (3,5 DIMETHYLBENZOYL) 4 METHYLPHENOXY]ETHYL]URACIL; 1 [2 [2 (3,5 DIMETHYLBENZYL) 4 METHYLPHENOXY]ETHYL]URACIL; 1 [2 [4 BROMO 2 (3,5 DICHLOROBENZOYL)PHENOXY]ETHYL]URACIL; 1 [2 [4 BROMO 2 (3,5 DIMETHYLBENZOYL)PHENOXY]ETHYL]URACIL; 1 [2 [4 BROMO 2 (3,5 DIMETHYLBENZYL)PHENOXY]ETHYL]URACIL; 1 [2 [4 CHLORO 2 (3 METHYLBENZOYL)PHENOXY]ETHYL]URACIL; 1 [2 [4 CHLORO 2 (3,5 DIBROMOBENZOYL)PHENOXY]ETHYL] 6 METHYLURACIL; 1 [2 [4 CHLORO 2 (3,5 DIBROMOBENZOYL)PHENOXY]ETHYL]URACIL; 1 [2 [4 CHLORO 2 (3,5 DICHLOROBENZOYL)PHENOXY]ETHYL]URACIL; 1 [2 [4 CHLORO 2 (3,5 DIFLUOROBENZOYL)PHENOXY]ETHYL]URACIL; 1 [2 [4 CHLORO 2 (3,5 DIMETHYLBENZOYL)PHENOXY]ETHYL]URACIL; 1 [2 [4 CHLORO 2 (3,5 DIMETHYLBENZYL)PHENOXY]ETHYL]URACIL; 1 [3 [4 CHLORO 2 (3,5 DIMETHYLBENZOYL)PHENOXY]ETHYL]THYMINE; ANTIRETROVIRUS AGENT; DELAVIRDINE; EFAVIRENZ; ETRAVIRINE; NEVIRAPINE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; RILPIVIRINE; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG RESISTANCE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; REVERSE TRANSCRIPTION; STRUCTURE ACTIVITY RELATION; VIRUS MUTANT; VIRUS STRAIN; WILD TYPE;

AMINO ACID SUBSTITUTION; BENZOPHENONES; CELL LINE; DRUG RESISTANCE, VIRAL; HIV REVERSE TRANSCRIPTASE; HIV-1; HUMANS; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; URACIL;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 80052950104     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.08.025     Document Type: Article

References (39)

1. H.I. Hall, R. Song, P. Rhodes, J. Prejean, Q. An, L.M. Lee, J. Karon, R. Brookmeyer, E.H. Kaplan, M.T. McKenna, and R.S. Janssen JAMA 300 2008 520
2. E. De Clercq Int. J. Antimicrob. Agents 33 2009 307
3. M.P. de Bethune Antiviral Res. 85 2010 75
4. R. Esnouf, J. Ren, C. Ross, Y. Jones, D. Stammers, and D. Stuart Nat. Struct. Biol. 2 1995 303
5. A. Ivetac, and J.A. McCammon J. Mol. Biol. 388 2009 644
6. Z. Zhou, X. Lin, and J.D. Madura Infect. Disord.: Drug Targets 6 2006 391
7. J. Balzarini Curr. Top. Med. Chem. 4 2004 921
8. E. De Clercq Antiviral Res. 38 1998 153
9. D. Jochmans Virus Res. 134 2008 171
10. H. Tanaka, H. Takashima, M. Ubasawa, K. Sekiya, I. Nitta, M. Baba, S. Shigeta, R.T. Walker, E. De Clercq, and T. Miyasaka J. Med. Chem. 35 1992 337
11. H. Tanaka, H. Takashima, M. Ubasawa, K. Sekiya, I. Nitta, M. Baba, S. Shigeta, R.T. Walker, E. De Clercq, and T. Miyasaka J. Med. Chem. 35 1992 4713
12. N.M. Goudgaon, and R.F. Schinazi J. Med. Chem. 34 1991 3305
13. B.-C. Pan, Z.-H. Chen, G. Piras, G.E. Dutschman, E.C. Rowe, Y.-C. Chen, and S.-H. Chu J. Heterocycl. Chem. 31 1994 177
14. D.-K. Kim, Y.-W. Kim, J. Gam, G. Kim, J. Lim, N. Lee, H.-T. Kim, and K.H. Kim J. Heterocycl. Chem. 33 1996 1275
15. R.W. Buckheit Jr., T.L. Hartman, K.M. Watson, S.G. Chung, and E.H. Cho Antimicrob. Agents Chemother. 52 2008 225
16. R.W. Buckheit Jr., T.L. Hartman, K.M. Watson, H.S. Kwon, S.H. Lee, J.W. Lee, D.W. Kang, S.G. Chung, and E.H. Cho Antiviral Chem. Chemother. 18 2007 259
17. N.R. El-Brollosy, P.T. Jorgensen, B. Dahan, A.M. Boel, E.B. Pedersen, and C. Nielsen J. Med. Chem. 45 2002 5721
18. H. Tanaka, H. Takashima, M. Ubasawa, K. Sekiya, N. Inouye, M. Baba, S. Shigeta, R.T. Walker, E. De Clercq, and T. Miyasaka J. Med. Chem. 38 1995 2860
19. M. Baba, S. Shigeta, S. Yuasa, H. Takashima, K. Sekiya, M. Ubasawa, H. Tanaka, T. Miyasaka, R.T. Walker, and E. De Clercq Antimicrob. Agents Chemother. 38 1994 688
20. M.L. Mitchell, J.C. Son, I.Y. Lee, C.K. Lee, H.S. Kim, H. Guo, J. Wang, J. Hayes, M. Wang, A. Paul, E.B. Lansdon, J.M. Chen, G. Eisenberg, R. Geleziunas, L. Xu, and C.U. Kim Bioorg. Med. Chem. Lett. 20 2010 1585
21. J. Ren, P.P. Chamberlain, A. Stamp, S.A. Short, K.L. Weaver, K.R. Romines, R. Hazen, A. Freeman, R.G. Ferris, C.W. Andrews, L. Boone, J.H. Chan, and D.K. Stammers J. Med. Chem. 51 2008 5000
22. J.H. Chan, G.A. Freeman, J.H. Tidwell, K.R. Romines, L.T. Schaller, J.R. Cowan, S.S. Gonzales, G.S. Lowell, C.W. Andrews 3rd, D.J. Reynolds, M. St Clair, R.J. Hazen, R.G. Ferris, K.L. Creech, G.B. Roberts, S.A. Short, K. Weaver, G.W. Koszalka, and L.R. Boone J. Med. Chem. 47 2004 1175
23. K.R. Romines, G.A. Freeman, L.T. Schaller, J.R. Cowan, S.S. Gonzales, J.H. Tidwell, C.W. Andrews 3rd, D.K. Stammers, R.J. Hazen, R.G. Ferris, S.A. Short, J.H. Chan, and L.R. Boone J. Med. Chem. 49 2006 727
24. C.S. Marvel Org. Synth. 1 1941 435
25. M.J. Robins, and P.W. Hatfield Can. J. Chem. 60 1982 547
26. K.K. Ogilvie, R.J. Hamilton, M.F. Gillen, and B.K. Radatus Can. J. Chem. 62 1984 16
27. V. Malik, P. Singh, and S. Kumar Tetrahedron 62 2006 5944
28. V. Malik, P. Singh, and S. Kumar Tetrahedron 61 2005 4009
29. F.-S. Tjoeng, E. Kraas, E. Breitmaier, and G. Jung Chem. Ber. 109 1976 2615
30. J.S. Nowick, J.S. Chen, and G. Noronha J. Am. Chem. Soc. 115 1993 7636
31. M.S. Novikov, and A.A. Ozerov Chem. Heterocycl. Comp. 41 2005 905
32. F. Wu, M.G. Buhendwa, and D.F. Weaver J. Org. Chem. 69 2004 9307
33. I.S. Salikhov, V.S. Reznik, Y.S. Shvetsov, and V.V. Petrova Russ. Chem. Bull. 35 1986 1064
34. B. Gu, V.K. Johnston, L.L. Gutshall, T.T. Nguyen, R.R. Gontarek, M.G. Darcy, R. Tedesco, D. Dhanak, K.J. Duffy, C.C. Kao, and R.T. Sarisky J. Biol. Chem. 278 2003 16602
35. M. Dixon Biochem. J. 55 1953 170
36. D.K. Pokholok, S.O. Gudima, D.S. Yesipov, V.N. Dobrynin, V.O. Rechinsky, and S.N. Kochetkov FEBS Lett. 325 1993 237
37. A.V. Ivanov, A.N. Korovina, V.L. Tunitskaya, D.A. Kostyuk, V.O. Rechinsky, M.K. Kukhanova, and S.N. Kochetkov Protein Expr. Purif. 48 2006 14
38. K. Rengan J. Chem. Ed. 60 1983 682
39. Y.-H. Liang, Q.-Q. He, Z.-S. Zeng, Z.-Q. Liu, X.-Q. Feng, F.-R. Chen, J. Balzarini, C. Pannecouque, and E. De Clercq Bioorg. Med. Chem. 18 2010 4601