Synthesis, structure-activity relationships, and docking studies of N-phenylarylformamide derivatives (PAFAs) as non-nucleoside HIV reverse transcriptase inhibitors

European Journal of Medicinal Chemistry

Volumn 58, Issue , 2012, Pages 504-512

  Ma, Xiao Dong ^a   He, Qiu Qin ^a   Zhang, Xuan ^b,c   Yang, Shi Qiong ^a   Yang, Liu Meng ^b   Gu, Shuang Xi ^a   Zheng, Yong Tang ^b   Chen, Fen Er ^a   Dai, Hui Fang ^a  

^a FUDAN UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Anti HIV activity; Benzophenone derivatives; N Phenylarylformamide; NNRTIs; Structure activity relationship

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; FORMAMIDE DERIVATIVE; GW 678248; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (1 NAPHTHOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (2 NAPHTHOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (2 NITROBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (2,4 DIMETHYLBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (2,5 DICHLOROBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (2,6 DICHLOROPHENYLACETYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3 CHLORO 5 BROMOBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3 CHLOROBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3 FLUOROBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3 METHYLBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3 NITROBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3 TRIFLUOROMETHYLBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3,4 DICHLOROBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3,4 DIMETHYLBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3,5 BROMOBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3,5 DICHLOROBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (3,5 DIMETHYLBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (4 METHOXYBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (4 METHYLBENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (BENOZYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [4 CHLORO 2 (BENZOYL)AMINOPHENOXY]ACETAMIDE; N[4 (AMINOSULFONYL) 2 METHYLPHENYL] 2 [[4 CHLORO 2 (CINNAMOYL)AMINOPHENOXY]ACETAMIDE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION; VIRUS STRAIN;

ANTI-HIV AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; FORMAMIDES; HIV REVERSE TRANSCRIPTASE; HIV-1; HIV-2; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; MOLECULAR STRUCTURE; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84869130548     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.03.032     Document Type: Article

References (45)

1. F. Barré-Sinoussi, J.C. Chermann, F. Rey, M.T. Nugeyre, S. Chamaret, J. Gruest, C. Dauguet, C. Axler-Blin, F. Vézinet-Brun, and C. Rouzioux Science 220 1983 868 871
2. R.C. Gallo, S.Z. Salahuddin, M. Popovic, G. Shearer, M. Kaplan, B. Haynes, T. Palker, R. Redfield, J. Oleske, and B. Safai Science 224 1984 500 503
3. F.J. Palella, K.M. Delaney, A.C. Moorman, M.O. Loveless, J. Fuhrer, G.A. Satten, D.J. Aschman, and S.D. Holmberg New Engl. J. Med. 338 1998 853 860
4. E. De Clercq Curr. Med. Chem. 8 2001 1543 1572
5. M.-P. de Béthune Antivir. Res. 58 2010 75 90
6. R.A. Koup, V.J. Merluzzi, K.D. Hargrave, J. Adams, K. Grozinger, R.J. Eclmer, and J.L. Sullivan J. Infect. Dis. 163 1991 966 970
7. W.W. Freimuth Adv. Exp. Med. Biol. 394 1996 279 289
8. S.D. Young, S.F. Britcher, L.O. Tran, L.S. Payne, W.C. Lumma, T.A. Lyle, J.R. Huff, P.S. Anderson, D.B. Olsen, and S.S. Carroll Antimicrob. Agents Chemother. 39 1995 2602 2605
9. J.J. Minuto, and R. Haubrich Future HIV Ther. 2 2008 525 537
10. L.B. Johnson, and L.D. Saravolatz Clin. Infect. Dis. 48 2009 1123 1128
11. D. Ripamonti, and F. Maggiolo Curr. Opin. Invest. Drugs 9 2008 899 912
12. P. Pecora Fulco, and I.R. McNicholl Pharmacotherapy 29 2009 281 294
13. K. Andries, H. Azijn, T. Thielemans, D. Ludovici, M. Kukla, J. Heeres, P. Janssen, B. De Corte, J. Vingerhoets, R. Pauwels, and M.-P. de Béthune Antimicrob. Agents Chemother. 48 2004 4680 4686
14. P.A. Janssen, P.J. Lewi, E. Arnold, F. Daeyaert, M. de Jonge, J. Heeres, L. Koymans, M. Vinkers, J. Guillemont, E. Pasquier, M. Kukla, D. Ludovici, K. Andries, M.-P. de Béthune, R. Pauwels, K. Das, A.D. Clark Jr., Y.V. Frenkel, S.H. Hughes, B. Medaer, F. De Knaep, H. Bohets, F. De Clerck, A. Lampo, P. Williams, and P. Stoffels J. Med. Chem. 48 2005 1901 1909
15. H. Azijn, I. Tirry, J. Vingerhoets, M.-P. de Béthune, G. Kraus, K. Boven, D. Jochmans, E. Van Craenenbroeck, G. Picchio, and L.T. Rimsky Antimicrob. Agents Chemother. 54 2010 718 727
16. S. Moreno, J. López Aldeguer, J.R. Arribas, P. Domingo, J.A. Iribarren, E. Ribera, A. Rivero, and F. Pulido J. Antimicrob. Agents Chemother. 65 2010 827 835
17. R.M. Grant, F.M. Hecht, M. Warmerdam, L. Liu, T. Liegler, C.J. Petropoulos, N.S. Hellmann, M. Chesney, M.P. Busch, and J.O. Kahn JAMA 288 2002 181 188
18. Z. Zhang, R. Hamatake, and Z. Hong Antivir. Chem. Chemother. 15 2004 121 134
19. 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. Andrews III, and D.J. Reynolds J. Med. Chem. 47 2004 1175 1182
20. R.J. Hazen, R.J. Harvey, M.H. St Clair, R.G. Ferris, G.A. Freeman, J.H. Tidwell, L.T. Schaller, J.R. Cowan, S.A. Short, and K.R. Romines Antimicrob. Agents Chemother. 49 2005 4465 4473
21. R.G. Ferris, R.J. Hazen, G.B. Roberts, M.H. St Clair, J.H. Chan, K.R. Romines, G.A. Freeman, J.H. Tidwell, L.T. Schaller, and J.R. Cowan Antimicrob. Agents Chemother. 49 2005 4046 4051
22. K.R. Romines, G.A. Freeman, L.T. Schaller, J.R. Cowan, S.S. Gonzales, J.H. Tidwell, C.W. Andrews III, D.K. Stammers, R.J. Hazen, and R.G. Ferris J. Med. Chem. 49 2006 727 739
23. T.J. Tucker, S. Saggar, J.T. Sisko, R.M. Tynebor, T.M. Williams, P.J. Felock, J.A. Flynn, M.T. Lai, Y. Liang, and G. McGaughey Bioorg. Med. Chem. Lett. 18 2008 2959 2966
24. A.A. San Juan Bioorg. Med. Chem. Lett. 18 2008 1181 1194
25. J. Ren, P.P. Chamberlain, A. Stamp, S.A. Short, K.L. Weaver, K.R. Romines, R. Hazen, A. Freeman, R.G. Ferris, and C.W. Andrews J. Med. Chem. 51 2008 5000 5008
26. P.G. Wyatt, R.C. Bethell, N. Cammack, D. Charon, N. Dodic, B. Dumaitre, D.N. Evans, D.V.S. Green, and P.L. Hopewell J. Med. Chem. 38 1995 1657 1665
27. F.A. Macías, J.M. De Siqueira, N. Chinchilla, D. Marín, R.M. Varela, and J.M.G. Molinillo J. Agr. Food Chem. 54 2006 9843 9851
28. J.P. Brown, and E.B. McCall J. Chem. Soc. 4 1955 3681 3687
29. Y.T. Zheng, K.L. Ben, and S.W. Jin Acta Pharmacol. Sin. 21 2000 179 182
30. R.R. Wang, L.M. Yang, Y.H. Wang, W. Pang, S.C. Tam, P. Tien, and Y.T. Zheng Biochem. Biophys. Res. Commun. 382 2009 540 544
31. X.Q. Feng, Y.H. Liang, Z.S. Zeng, F.E. Chen, J. Balzarini, C. Pannecouque, and E. De Clercq ChemMedChem 4 2009 219 224
32. Y.P. He, F.E. Chen, G.F. Sun, Y.P. Wang, E. De Clercq, J. Balzarini, and C. Pannecouque Bioorg. Med. Chem. Lett. 14 2004 3173 3176
33. L. Ji, F.E. Chen, E. De Clercq, J. Balzarini, and C. Pannecouque J. Med. Chem. 50 2007 1778 1786
34. Y.H. Liang, X.Q. Feng, Z.S. Zeng, F.E. Chen, J. Balzarini, C. Pannecouque, and E. De Clercq ChemMedChem 4 2009 1537 1545
35. Y.P. Wang, F.E. Chen, E. De Clercq, J. Balzarini, and C. Pannecouque Bioorg. Med. Chem. 16 2008 3887 3894
36. M.Y. Yu, Z.Y. Li, S. Liu, E.K. Fan, C. Pannecouque, E. De Clercq, and X.Y. Liu ChemMedChem 6 2011 826 833
37. J. Park, and N.-D. Sung Bull. Korean Chem. Soc. 31 2011 1241 1248
38. Q. Liu, B. Masek, K. Smith, and J. Smith J. Med. Chem. 50 2007 5392 5402
39. A.N. Jain J. Comput. Aided Mol. Des. 10 1996 427 440
40. A.N. Jain J. Comput. Aided Mol. Des. 21 2007 281 306
41. A.N. Jain J. Med. Chem. 46 2003 499 511
42. J.Z. Chen, J. Wang, and X.Q. Xie J. Chem. Inform. Model. 47 2007 1626 1637
43. S. Raduner, A. Majewska, J.Z. Chen, X.Q. Xie, J. Hamon, B. Faller, K.H. Altmann, and J. Gertsch J. Biol. Chem. 281 2006 14192 14206
44. J. Ruppert, W. Welch, and A.N. Jain Protein Sci. 6 1997 524 533
45. W. Welch, J. Ruppert, and A.N. Jain Chem. Biol. 3 1996 449 462