Design and synthesis of potent HIV-1 protease inhibitors incorporating hydroxyprolinamides as novel P2 ligands

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 12, 2011, Pages 3730-3733

  Gao, Bing Lei ^a   Zhang, Cheng Mei ^a   Yin, Yi Zhen ^a   Tang, Long Qian ^a   Liu, Zhao Peng ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Design; Drug resistant; HIV 1 protease inhibitors; Hydroxyprolinamide; P2 ligand; Synthesis

Indexed keywords

DARUNAVIR; HYDROXYPROLINAMIDE DERIVATIVE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; LIGAND BINDING; MOLECULAR DOCKING; SUBSTITUTION REACTION; VIRUS INHIBITION;

AMIDES; BINDING SITES; DRUG DESIGN; HIV PROTEASE INHIBITORS; HIV-1; HUMANS; HYDROXYPROLINE; INHIBITORY CONCENTRATION 50; LIGANDS; MOLECULAR STRUCTURE; SULFONAMIDES;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 79957866241     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.04.070     Document Type: Article

References (20)

1. Brik, A.; Wong, C.-H. Org. Biomol. Chem. 2003, 1, 5.
2. Randolph, J. T.; DeGoey, D. A. Curr. Top. Med. Chem. 2004, 4, 1079.
3. De Clercq, E. J. Med. Chem. 2005, 48, 1297.
4. Sepkowitz, K. A. N. Engl. J. Med. 2001, 344, 1764.
5. De Clercq, E. Int. J. Antimicrob. Agents 2009, 33, 307.
6. Rodriguez-Barrios, F.; Gago, F. Curr. Top. Med. Chem. 2004, 4, 991.
7. Lucas, G. M. J. Antimicrob. Chemother. 2005, 55, 413.
8. Armbruster, C. Anti-Infect. Agents Med. Chem. 2008, 7, 201.
9. Anderson, J.; Schiffer, C.; Lee, S.-K.; Swanstrom, R. V. Handb. Exp. Pharmacol. 2009, 189, 85.
10. Mastrolorenzo, A.; Rusconi, S.; Scozzafava, A.; Barbaro, G.; Supuran, C. T. Curr. Med. Chem. 2007, 14, 2734.
11. Clavel, F.; Hance, A. J. N. Engl. J. Med. 2004, 350, 1023.
12. Grant, R. M.; Hecht, F. M.; Warmerdam, M.; Liu, L.; Liegler, T.; Petropoulos, C. J.; Hellmann, N. S.; Chesney, M.; Busch, M. P.; Kahn, J. O. J. Am. Med. Assoc. 2002, 288, 181.
13. Hue, S.; Gifford, R. J.; Dunn, D.; Fernhill, E.; Pillay, D. J. Virol. 2009, 83, 2645.
14. Tie, Y.; Boross, P. I.; Wang, Y.-F.; Gaddis, L.; Hussain, A. K.; Leshchenko, S.; Ghosh, A. K.; Louis, J. M.; Harrison, R. W.; Weber, I. T. H. J. Mol. Biol. 2004, 338, 341.
15. King, N. M.; Prabu-Jeyabalan, M.; Nalivaika, E. A.; Wigerinck, P.; de Bethune, M.-P.; Schiffer, C. A. J. Virol. 2004, 78, 12012.
16. Kovalevsky, A. Y.; Liu, F.; Leshchenko, S.; Ghosh, A. K.; Louis, J. M.; Harrison, R. W.; Weber, I. T. J. Mol. Biol. 2006, 363, 161.
17. Ghosh, A. K.; Chapsal, B. D.; Weber, I. T.; Mitsuya, H. Acc. Chem. Res. 2008, 41, 78.
18. Tamaki, M.; Han, G. X.; Hruby, J. V. J. Org. Chem. 2001, 66, 3593.
19. Ghosh, A. K.; Leshchenko, S.; Noetzel, M. J. Org. Chem. 2004, 69, 7822.
20. Ali, A.; Reddy, G. S. K. K.; Cao, H.; Anjum, S. G.; Nalam, M. N. L.; Schiffer, C. A.; Rana, T. M. J. Med. Chem. 2006, 49, 7342.