Arylthiopyrrole (AThP) derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors: Synthesis, structure-activity relationships, and docking studies (Part 1)

ChemMedChem

Volumn 1, Issue 12, 2006, Pages 1367-1378

  Di Santo, Roberto Di ^a   Costi, Roberta ^a   Artico, Marino ^a   Miele, Gaetano ^a   Lavecchia, Antonio ^b   Novellino, Ettore ^b   Bergamini, Alberto ^c   Cancio, Reynel ^d   Maga, Giovanni ^d  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c UNIVERSITY OF ROME TOR VERGATA   (Italy)

^d CNR   (Italy)

Author keywords

AIDS; Antiviral agents; Arylthiopyrroles; HIV; NNRTI

Indexed keywords

LIGAND; PYRROLE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ARTICLE; BINDING SITE; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; DRUG ANTAGONISM; DRUG DESIGN; HUMAN; MICROBIOLOGICAL EXAMINATION; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BINDING SITES; CELL LINE; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HIV-1 REVERSE TRANSCRIPTASE; HUMANS; LIGANDS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRROLES; REVERSE TRANSCRIPTASE INHIBITORS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33846262498     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200600119     Document Type: Article

References (33)

1. F. J. Palella, K. M. Delaney, A. C. Moorman, M. O. Loveless, J. Fuhrer, G. A. Satten, D. J. Aschman, S. D. Holmberg, N. Engl. J. Med. 1998, 338, 853-860.
2. S. Vella, L. Palmisano, Antiviral Res. 2000, 45, 1-7.
3. G. Hajos, Z. Riedl, J. Molnar, D. Szabo, Drugs Future 2000, 25, 47-62.
4. W. Schäfer, W.-G. Friebe, H. Leinert, A. Mertens, T. Poll, W. von der Saal, H. Zilch, B. Nuber, M. L. Ziegler, J. Med. Chem. 1993, 36, 726-732.
5. L. A. Kohlstaedt, J. Wang, J. M. Friedman, P. A. Rice, T. A. Steitz, Science 1992, 256, 1783-1790.
6. "Reservoirs for HIV-1": R. F. Siliciano, Curr. Infect. Dis. Rep. 1999, 1, 298-304.
7. M. R. Furtado, D. S. Callaway, J. P. Phair, K. J. Kunstman, J. L. Stanton, C. A. Macken, A. S. Perelson, S. M. Wolinsky, N. Engl. J. Med. 1999, 340, 1614-1622.
8. R. A. Koup, V. J. Merluzzi, K. D. Hargrave, J. Adams, K. Grozinger, R. J. Eckner, J. L. Sullivan, J. Infect. Dis. 1991, 163, 966-970.
9. W. W. Freimuth, Adv. Exp. Med. Biol. 1996, 394, 279-289.
10. 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, S. S. Carroll, D. J. Pettibone, J. A. O'Brien, R. G. Ball, S. K. Balani, J. H. Lin, I.-W. Chen, W. A. Schleif, V. V. Sardana, W. J. Long, V. W. Byrnes, E. A. Emini, Antimicrob. Agents Chemother. 1995, 39, 2602-2605.
11. E. De Clercq, Chem. Biodiversity 2004, 1, 44-64.
12. D. C. Meadows, J. Gervay-Hague, ChemMedChem 2006, 1, 16-29.
13. a) T. Fujiwara, A. Sato, M. El-Farrash, S. Miki, K. Abe, Y. Isaka, M. Kodama, Y. Wu, L. B. Chen, H. Harada, H.; Sugimoto, M. Hatanaka, Y. Hinuma, Antimicrob. Agents Chemother. 1998, 42, 1340-1345;
14. b) T. Fujiwara, A. Sato, A. K. Patick, K. E. Potts, Int. Antiviral News 1999, 7, 18-20.
15. J. Ren, C. Nichols, L. E. Bird, T. Fujiwara, H. Sugimoto, D. I. Stuart, D. K. Stammers, J. Biol. Chem. 2000, 275, 14316-14320.
16. M. Hajima, Y. Hozumi, M. Kabaki, WO 199829395, 1998 [Chem. Abstr. 1998, 129, 95494].
17. R. Di Santo, R. Costi, M. Artico, R. Ragno, S. Massa, M. La Colla, R. Loddo, P. La Colla, A. Pani, Med. Chem. Res. 2002, 12, 153-167.
18. V. J. Merluzzi, K. D. Hargrave, M. Labadia, K. Grozinger, M. Skoog, J. C. Wu, C.-K. Shih, K. Eckner, S. Hattox, J. Adams, A. S. Rosenthal, R. Faanes, R. J. Eckner, R. A. Koup, J. L. Sullivan, Science 1990, 250, 1411-1413.
19. GOLD 2.2, CCDC Software Limited, Cambridge, UK, 2004.
20. G. Jones, P. Willett, R. C. Glen, A. R. Leach, R. J. Taylor, J. Mol. Biol. 1997, 267, 727-748.
21. G. Jones, P. Willett, R. C. Glen, J. Mol. Biol. 1995, 245, 43-53.
22. C. Bissantz, G. Folkers, D. Rognan, J. Med. Chem. 2000, 43, 4759-4767.
23. G. Schneider, H. Bohm, Drug Discovery Today 2002, 7, 64-70.
24. R. F. Schinazi, B. A. Larder, J. W. Mellors, Int. Antiviral News 1997, 5, 129-135.
25. R. Esnouf, J. Ren, C. Ross, Y. Jones, D. Stammers, D. Stuart, Nat. Struct. Biol. 1995, 2, 303-308.
26. Y. Hsiou, J. Ding, K. Das, A. D. Clark, Jr., P. L. Boyer, P. Lewi, P. A. J. Janssen, J. P. Kleim, M. Rösner, S. H. Hughes, E. Arnold, J. Mol. Biol. 2001, 309, 437-445.
27. F. Rodriguez-Barrios, J. Balzarini, F. Gago, J. Am. Chem. Soc. 2005, 127, 7570-7578.
28. A. Lavecchia, R. Costi, M. Artico, G. Miele, E. Novellino, A. Bergamini, E. Crespan, G. Maga, R. Di Santo, ChemMedChem 2006, 1, 1379-1390.
29. R. Pauwels, J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter, E. De Clercq, J. Virol. Methods 1988, 20, 309-321.
30. M. Botta, M. Artico, S. Massa, A. Gambacorta, M. E. Marongiu, A. Pani, P. La Colla, Eur. J. Med. Chem. 1992, 27, 251-257.
31. J. G. Vinter, A. Davis, M. R. Saunders, J. Comput.-Aided Mol. Des. 1987, 1, 31-51.
32. A. T. Hagler, S. Lifson, P. Dauber, J. Am. Chem. Soc. 1979, 101, 5122-5130.
33. "The PyMOL Molecular Graphics System": W. L. DeLano, 2002 http://pymol.sourceforge.net/.