Discovery of piperidine-linked pyridine analogues as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

ChemMedChem

Volumn 8, Issue 7, 2013, Pages 1117-1126

  Chen, Xuwang ^a   Li, Yuanyuan ^a   Ding, Shufang ^a   Balzarini, Jan ^b   Pannecouque, Christophe ^b   DeClercq, Erik ^b   Liu, Huiqing ^a   Liu, Xinyong ^a  

^a SHANDONG UNIVERSITY   (China)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antiviral agents; Biological activity; HIV 1; Molecular simulations; Reverse transcriptase

Indexed keywords

4 ((4 (6 (MESITYLAMINO) 3 NITROPYRIDIN 2 YLAMINO)PIPERIDIN 1 YL) METHYL)BENZENESULFONAMIDE; BENZENESULFONAMIDE DERIVATIVE; DELAVIRDINE; EFAVIRENZ; ETRAVIRINE; HUMAN IMMUNODEFICIENCY VIRUS ANTIBODY; NEVIRAPINE; PIPERIDINE; PYRIDINE; RILPIVIRINE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ARTICLE; CYTOTOXICITY; DRUG POTENTIATION; FOOD AND DRUG ADMINISTRATION; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; WILD TYPE;

ANTI-HIV AGENTS; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; HIV REVERSE TRANSCRIPTASE; HIV-1; HUMANS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; MOLECULAR STRUCTURE; PIPERIDINES; PYRIDINES; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84879782469     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201300130     Document Type: Article

References (25)

1. UNAIDS Report on the Global AIDS Epidemic, 2012; http://www.unaids.org/en/resources/publications/2012/name, 76121, en.asp.
2. Y. Mehellou, E. DeClercq, J. Med. Chem. 2010, 53, 521-538.
3. T. Hawkins, Antiviral Res. 2010, 85, 201-209;
4. R. Paredes, B. Clotet, Antiviral Res. 2010, 85, 245-265.
5. X. W. Chen, P. Zhan, D. Y. Li, E. DeClercq, X. Y. Liu, Curr. Med. Chem. 2011, 18, 359-376.
6. D. J. Kertesz, C. Brotherton-Pleiss, M. M. Yang, Z. G. Wang, X. F. Lin, Z. X. Qiu, D. R. Hirschfeld, S. Gleason, T. Mirzadegan, P. W. Dunten, S. F. Harris, A. G. Villasenor, J. Q. Hang, G. M. Heilek, K. Klumpp, Bioorg. Med. Chem. Lett. 2010, 20, 4215-4218.
7. X. Chen, P. Zhan, X. Liu, Z. Cheng, C. Meng, S. Shao, C. Pannecouque, E. DeClercq, X. Liu, Bioorg. Med. Chem. 2012, 20, 3856-3864;
8. X. Chen, P. Zhan, C. Pannecouque, J. Balzarini, E. DeClercq, X. Liu, Eur. J. Med. Chem. 2012, 51, 60-66.
9. X. Tian, B. Qin, H. Lu, W. Lai, S. Jiang, K. H. Lee, C. H. Chen, L. Xie, Bioorg. Med. Chem. Lett. 2009, 19, 5482-5485;
10. X. Tian, B. Qin, Z. Wu, X. Wang, H. Lu, S. L. Morris-Natschke, C. H. Chen, S. Jiang, K. H. Lee, L. Xie, J. Med. Chem. 2010, 53, 8287-8297.
11. S. M. Bowen, J. T. Lundquist IV, J. F. Mehlmann, J. C. Pelletier, M. D. Vera, (Wyeth LLC), Patent WO2009029609, 2009 [ Chem. Abstr. 2009, 150, 306649].
12. A. Palani, S. Shapiro, M. D. McBriar, J. W. Clader, W. J. Greenlee, B. Spar, T. J. Kowalski, C. Farley, J. Cook, M. vanHeek, B. Weig, K. O'Neill, M. Graziano, B. Hawes, J. Med. Chem. 2005, 48, 4746-4749.
13. C. Pannecouque, D. Daelemans, E. DeClercq, Nat. Protoc. 2008, 3, 427-434.
14. S. X. Gu, S. Q. Yang, Q. Q. He, X. D. Ma, F. E. Chen, H. F. Dai, E. D. Clercq, J. Balzarini, C. Pannecouque, Bioorg. Med. Chem. 2011, 19, 7093-7099.
15. R. T. D′Aquila, J. M. Schapiro, F. Brun-Vezinet, B. Clotet, B. Conway, L. M. Demeter, R. M. Grant, V. A. Johnson, D. R. Kuritzkes, C. Loveday, R. W. Shafer, D. D. Richman, Top HIV Med. 2003, 11, 92-96.
16. P. A. Janssen, P. J. Lewi, E. Arnold, F. Daeyaert, M. deJonge, J. Heeres, L. Koymans, M. Vinkers, J. Guillemont, E. Pasquier, M. Kukla, D. Ludovici, K. Andries, M. P. deBethune, R. Pauwels, K. Das, A. D. Clark, Jr., Y. V. Frenkel, S. H. Hughes, B. Medaer, F. DeKnaep, H. Bohets, F. DeClerck, A. Lampo, P. Williams, P. Stoffels, J. Med. Chem. 2005, 48, 1901-1909;
17. E. B. Lansdon, K. M. Brendza, M. Hung, R. Wang, S. Mukund, D. Jin, G. Birkus, N. Kutty, X. Liu, J. Med. Chem. 2010, 53, 4295-4299;
18. K. Das, J. D. Bauman, A. D. Clark, Jr., Y. V. Frenkel, P. J. Lewi, A. J. Shatkin, S. H. Hughes, E. Arnold, Proc. Natl. Acad. Sci. USA 2008, 105, 1466-1471.
19. The PyMOL Molecular Graphics System, version 0.99, DeLano Scientific, San Carlos, CA (USA), 2002.
20. M. Popovic, M. G. Sarngadharan, E. Read, R. Gallo, Science 1984, 224, 497-500.
21. F. Clavel, D. Guetard, F. Brun-Vezinet, S. Chamaret, M. A. Rey, M. O. Santos-Ferreira, A. G. Laurent, C. Dauguet, C. Katlama, C. Rouzioux, D. Klatzmann, J. L. Champalimaud, L. Montagnier, Science 1986, 233, 343-346.