Substituent effects on P2-cyclopentyltetrahydrofuranyl urethanes: Design, synthesis, and X-ray studies of potent HIV-1 protease inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 6, 2012, Pages 2308-2311

  Ghosh, Arun K ^a   Chapsal, Bruno D ^a   Steffey, Melinda ^a   Agniswamy, Johnson ^b   Wang, Yuan Fang ^b   Amano, Masayuki ^c   Weber, Irene T ^b   Mitsuya, Hiroaki ^c,d  

^a PURDUE UNIVERSITY   (United States)

^b GEORGIA STATE UNIVERSITY   (United States)

^c KUMAMOTO UNIVERSITY   (Japan)

^d NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Design and synthesis; Drug resistance; HIV 1 protease inhibitors; P2 ligand; X ray crystal structure

Indexed keywords

CYCLOPENTYLTETRAHYDROFURANYL URETHANE DERIVATIVE; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; URETHAN DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CRYSTAL STRUCTURE; DRUG BINDING SITE; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

BINDING SITES; CRYSTALLOGRAPHY, X-RAY; CYCLOPENTANES; DRUG DESIGN; DRUG RESISTANCE, VIRAL; FURANS; HIV PROTEASE; HIV PROTEASE INHIBITORS; HIV-1; HUMANS; LEUKOCYTES, MONONUCLEAR; MODELS, MOLECULAR; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; URETHANE;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 84862793558     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.01.061     Document Type: Article

References (20)

1. B. Conway Future Virol. 4 2009 39
2. S. Hue, R.J. Gifford, D. Dunn, E. Fernhill, and D. Pillay J. Virol. 83 2009 2645
3. S.J. Little, S. Holte, J.P. Routy, E.S. Daar, M. Markowitz, A.C. Collier, R.A. Koup, J.W. Mellors, E. Connick, B. Conway, M. Kilby, L. Wang, J.M. Whitcomb, N.S. Hellmann, and D.D.N. Richman Engl. J. Med. 347 2002 385
4. A.K. Ghosh J. Med. Chem. 52 2009 2163
5. A.K. Ghosh, P.R. Sridhar, S. Leshchenko, A.K. Hussain, J. Li, A.Y. Kovalevsky, D.E. Walters, J.E. Wedekind, V. Grum-Tokars, D. Das, Y. Koh, K. Maeda, H. Gatanaga, I.T. Weber, and H. Mitsuya J. Med. Chem. 49 2006 5252
6. A.K. Ghosh, Z.L. Dawson, and H. Mitsuya Bioorg. Med. Chem. Lett. 15 2007 7576
7. A.K. Ghosh, S. Leshchenko-Yashchuk, D.D. Anderson, A. Baldridge, M. Noetzel, H.B. Miller, Y.F. Tie, Y.F. Wang, Y. Koh, I.T. Weber, and H. Mitsuya J. Med. Chem. 52 2009 3902
8. A.K. Ghosh, B.D. Chapsal, I.T. Weber, and H. Mitsuya Acc. Chem. Res. 41 2008 78
9. A.K. Ghosh, B.D. Chapsal, G.L. Parham, M. Steffey, J. Agniswamy, Y.-F. Wang, M. Amano, I.T. Weber, and H. Mitsuya J. Med. Chem. 54 2011 5890
10. A.K. Ghosh, B.D. Chapsal, A. Baldridge, K. Ide, Y. Koh, and H. Mitsuya Org. Lett. 10 2008 5135
11. J.J. Li, J.C. Sutton, A. Nirschl, Y. Zou, H. Wang, C. Sun, Z. Pi, R. Johnson, S.R. Krystek, R. Seethala, R. Golla, P.G. Sleph, B.C. Beehler, G.J. Grover, A. Fura, V.P. Vyas, C.Y. Li, J.Z. Gougoutas, M.A. Galella, R. Zahler, J. Ostrowski, and L.G. Hamann J. Med. Chem. 50 2007 3015
12. M.V. Toth, and G.R. Marshall Int. J. Pept. Protein Res. 36 1990 544
13. Y. Koh, H. Nakata, K. Maeda, H. Ogata, G. Bilcer, T. Devasamudram, J.F. Kincaid, P. Boross, Y.-F. Wang, Y. Tie, P. Volarath, L. Gaddis, R.W. Harrison, I.T. Weber, A.K. Ghosh, and H. Mitsuya Antimicrob. Agents Chemother. 47 2003 3123
14. A.K. Ghosh, and B. Chapsal Mitsuya, H A. Ghosh, Aspartic Acid Proteases as Therapeutic Targets 2010 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim 245 262
15. B. Mahalingam, J.M. Louis, J. Hung, R.W. Harrison, and I.T. Weber Proteins 43 2001 455
16. C.-H. Shen, Y.-F. Wang, A.Y. Kovalevsky, R.W. Harrison, and I.T. Weber FEBS J. 277 2010 3699
17. E. Potterton, P. Briggs, M. Turkenburg, and E.A. Dodson Acta Crystallogr. Sect. D: Bio. Crystallogr. 59 2003 1131
18. P. Emsley, and K. Cowtan Sect. D: Bio. Crystallogr. 60 2004 2126
19. A.W. Schuttelkopf, and D.M.F. van Aalten Acta Crystallogr. Sect. D: Bio. Crystallogr. 60 2004 1355
20. A.Y. Kovalevsky, F. Liu, S. Leshchenko, A.K. Ghosh, J.M. Louis, R.W. Harrison, and I.T. Weber J. Mol. Biol. 363 2006 161