Design, synthesis, and biological evaluations of novel quinolones as HIV-1 non-nucleoside reverse transcriptase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 16, 2006, Pages 4246-4251

  Ellis, David ^a   Kuhen, Kelli L ^a   Anaclerio, Beth ^a   Wu, Baogen ^a   Wolff, Karen ^a   Yin, Hong ^a   Bursulaya, Badry ^a   Caldwell, Jeremy ^a   Karanewsky, Donald ^a   He, Yun ^a  

^a GENOMICS INSTITUTE OF THE NOVARTIS RESEARCH FOUNDATION   (United States)

Author keywords

HIV replication; HIV 1 non nucleoside reverse transcriptase inhibitor (NNRTI); Molecule modeling; Quinolones; SAR

Indexed keywords

EFAVIRENZ; NEVIRAPINE; QUINOLONE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ARTICLE; BIOASSAY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; VIRUS REPLICATION;

BINDING SITES; DRUG RESISTANCE, VIRAL; HIV-1; HIV-1 REVERSE TRANSCRIPTASE; MODELS, CHEMICAL; MODELS, MOLECULAR; MUTATION; QUINOLONES; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 33745699185     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.05.073     Document Type: Article

References (17)

1. Locatelli G.A., Cancio R., Spadari S., and Maga G. Curr. Drug Metab. 5 (2004) 283
2. De Clercq E. Chem. Biodiversity 1 (2004) 44
3. Gotte M. Expert Rev. Anti-Infect. Ther. 2 (2004) 707
4. Barbaro G., Scozzafava A., Mastrolorenzo A., and Supuran C.T. Curr. Pharm. Des. 11 (2005) 1805
5. Maggiolo F., Ripamonti D., and Suter F. J. Antimicrob. Chemother. 5 (2005) 821
6. Marks K., and Gulick R.M. HIV Chemother. (2005) 1
7. Wainberg M.A., Sawyer J.P.C., Montaner J.S.G., Murphy R.L., Kuritzkes D.R., and Raffi F. Antiviral Ther. 10 (2005) 13
8. Jiang T., Kuhen K.L., Wolff K., Yin H., Bieza K., Caldwell J., Bursulaya' B., Wu T.Y.-H., and He Y. Bioorg. Med. Chem. Lett. 16 (2006) 2105
9. Jiang T., Kuhen K.L., Wolff K., Yin H., Bieza K., Caldwell J., Bursulaya' B., Tuntland T., Zhang K., Karanewsky D., and He Y. Bioorg. Med. Chem. Lett. 16 (2006) 2109
10. Wu B., Kuhen K., Nguyen T.N., Ellis D., Anaclerio B., He X., Yang K., Karanewsky D., Yin H., Wolff K., Bieza K., Caldwell J., and He Y. Bioorg. Med. Chem. Lett. 16 (2006) 3430
11. Wang Z., Wu B., Kuhen K.L., Nguyen T.N., Nguyen D.G., Bursulaya B., and He Y. Bioorg. Med. Chem. Lett. 16 (2006) 0000
12. Kleim J.-P., Bender R., Kirsch R., Meichsner C., Paessens A., Roesner M., Ruebsamen-Waigmann H., Kaiser R., and Wichers M. Antimicrob. Agents Chemother. 39 (1995) 2253
13. All compounds reported are racemic, and only one enantiomer is shown. Data are based on the measurement of the racemic mixture.
14. Meyers A.I., Romine J.L., and Fleming S.A. J. Am. Chem. Soc. 110 (1988) 7245
15. Molecular modeling and assays were carried out as described in Refs. 8 and 9.
16. The free energy of binding was obtained by subtracting the ligand and receptor energies from that of the complex. For the free energy calculations the OPLS-AA force field (Macromodel, Schrodinger Inc) was employed. The solvation was accounted for via Generalized Born method.
17. Irie H., Matsumoto R., Nishimura M., and Zhang Y. Chem. Pharm. Bull. 38 (1990) 1852