Imidazo[1,2-a]pyridin-3-amines as potential HIV-1 non-nucleoside reverse transcriptase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 14, 2011, Pages 4227-4237

  Bode, Moira L ^a   Gravestock, David ^a   Moleele, Simon S ^a   Van Der Westhuyzen, Christiaan W ^a   Pelly, Stephen C ^a,b   Steenkamp, Paul A ^a   Hoppe, Heinrich C ^a   Khan, Tasmiyah ^a   Nkabinde, Lindiwe A ^a  

^a CSIR Biosciences   (South Africa)

^b STELLENBOSCH UNIVERSITY   (South Africa)

Author keywords

Antiretroviral; Groebke reaction; HIV; Imidazo 1,2 a pyridine; NNRTI; Reverse transcriptase

Indexed keywords

2 (2 BROMOPHENYL) N CYCLOHEXYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; 2 (2 CHLOROPHENYL) 3 (CYCLOHEXYLAMINO)IMIDAZO[1,2 A]PYRIDINE 5 CARBONITRILE; 2 (2 CHLOROPHENYL) N CYCLOHEXYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; 2 (3 BROMOPHENYL) N CYCLOHEXYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; 2 (3 CHLOROPHENYL) N CYCLOHEXYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; 2 (4 BROMOPHENYL) N CYCLOHEXYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; 2 (4 CHLOROPHENYL) N CYCLOHEXYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; 2 AMINOPYRIDINE DERIVATIVE; 2 CHLOROBENZALDEHYDE; 2 SEC BUTYL N CYCLOHEXYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; CYCLOHEXYL ISOCYANIDE; ETRAVIRINE; IMIDAZO[1,2 A]PYRIDINE AMINE DERIVATIVE; ISOPROPYL N (PENTAN 2 YL)IMIDAZO[1,2 A]PYRIDIN 3 AMINE; ISOPROPYL N PENTYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; N BUTYL 2 ISOPROPYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; N CYCLOHEXYL 2 (2 FLUOROPHENYL)IMIDAZO[1,2 A]PYRIDIN 3 AMINE; N CYCLOHEXYL 2 (4 FLUOROPHENYL)IMIDAZO[1,2 A]PYRIDIN 3 AMINE; N CYCLOHEXYL 2 [2 (TRIFLUOROPHENYL)PHENYL]IMIDAZO[1,2 A]PYRIDIN 3 AMINE; N CYCLOHEXYL 2 [4 (TRIFLUOROPHENYL)PHENYL]IMIDAZO[1,2 A]PYRIDIN 3 AMINE; N CYCLOHEXYL 2 CYCLOPROPYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; N CYCLOHEXYL 2 ISOPROPYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; N CYCLOHEXYL 2 OCTYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; N CYCLOHEXYL 2 PHENYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; N CYCLOPENTYL 2 ISOPROPYLIMIDAZO[1,2 A]PYRIDIN 3 AMINE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; REAGENT; RILPIVIRINE; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; IC 50; MOLECULAR MODEL; SOLVENT EFFECT;

CELL LINE; CELL SURVIVAL; HIV REVERSE TRANSCRIPTASE; HIV-1; HUMANS; IMIDAZOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIDINES; REVERSE TRANSCRIPTASE INHIBITORS; SMALL MOLECULE LIBRARIES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 79960004985     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.05.062     Document Type: Article

References (30)

1. J. Balzarini Curr. Top. Med. Chem. 4 2004 921
2. L.R. Boone Curr. Opin. Invest. Drugs 7 2006 128
3. M.-P. De Béthune Antiviral Res. 85 2010 75
4. J.W. Corbett Curr. Med. Chem.: Anti-Infect. Agents 1 2002 119
5. R. Pauwels Curr. Opin. Pharmacol. 4 2004 437
6. C.E. Mowbray, C. Burt, R. Corbau, M. Perros, I. Tran, P.A. Stupple, R. Webster, and A. Wood Bioorg. Med. Chem. Lett. 19 2009 5599
7. P. Zhan, X. Liu, Z. Li, Z. Fang, Z. Li, D. Wang, C. Pannecouque, and E. De Clercq Bioorg. Med. Chem. 17 2009 5920
8. D. Jochmans Virus Res. 134 2008 171
9. P. Zhan, X. Liu, Z. Fang, Z. Li, C. Pannecouque, and E. De Clercq Eur. J. Med. Chem. 44 2009 4648
10. M.L. Mitchell, J.C. Son, I.Y. Lee, C.-K. Lee, H.S. Kim, H. Guo, J. Wanga, J. Hayes, M. Wanga, A. Paul, E.B. Lansdon, J.M. Chen, G. Eisenberg, R. Geleziunas, L. Xu, and C.U. Kim Bioorg. Med. Chem. Lett. 20 2010 1585
11. C.S. Leung, J.G. Zeevaart, R.A. Domaoal, M. Bollini, V.V. Thakur, K.A. Spasov, K.S. Anderson, and W.L. Jorgensen Bioorg. Med. Chem. Lett. 20 2010 2485
12. M. Weitman, K. Lerman, A. Nudelman, D.T. Major, A. Hizi, and A. Herschhorn Eur. J. Med. Chem. 46 2011 447
13. J.E. Starrett Jr., T.A. Montzka, A.R. Croswell, and R.L. Cavanagh J. Med. Chem. 32 1989 2204
14. A.M. Palmer, S. Chrismann, G. Münch, C. Brehm, P.J. Zimmermann, W. Buhr, J. Senn-Bilfinger, M.P. Feth, and W.A. Simon Bioorg. Med. Chem. 17 2009 368
15. Michiaki, T.; Yung-Hsiung, Y.; Kazuyuki, N.; Hidenori, O. Patent EP52016, 1981.
16. Maul, C.; Sundermann, B.; Hennies, H.-H.; Schneider, J.; Gerlach, M. Patent WO01027109, 2001.
17. A. Gueiffier, S. Mavel, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.-C. Teulade, M. Witvrouw, J. Balzarini, E. De Clercq, and J.-P. Chapat J. Med. Chem. 41 1998 5108
18. Defosse, G.; Le Ber, P.; Saarmets, A.; Wick. A. Patent FR2699919, 1994.
19. Elleder, D.; Young, J. A. T.; Baiga, T. J.; Noel, J. P. Patent WO2009061856, 2009.
20. J.-B. Véron, H. Allouchi, C. Enguehard-Gueiffier, R. Snoeck, G. Andrei, E. De Clercq, and A. Gueiffier Bioorg. Med. Chem. 16 2008 9536
21. K.S. Gudmundsson, and B.A. Johns Bioorg. Med. Chem. Lett. 17 2007 2735
22. C. Enguehard-Gueiffier, and A. Gueiffier Mini.-Rev. Med. Chem. 7 2007 888
23. Bode, M. L.; Rousseau, A. L.; Gravestock, D.; Moleele, S. S.; Van der Westhuyzen, C.W. WO 2010032195, 2010.
24. K. Groebke, L. Weber, and F. Mehlin Synlett 1998 661
25. C. Blackburn, B. Guan, P. Fleming, K. Shiosaki, and S. Tsai Tetrahedron Lett. 39 1998 3635
26. A.L. Rousseau, P. Matlaba, and C.J. Parkinson Tetrahedron Lett. 48 2007 4079
27. E.B. Lansdon, K.M. Brendza, M. Hung, R. Wang, S. Mukund, D. Jin, G. Birkus, N. Kutty, and X. Liu J. Med. Chem. 53 2010 4295
28. D.G. Prajapati, R. Ramajayam, M.R. Yadav, and R. Giridhar Bioorg. Med. Chem. 17 2009 5744
29. A.K. Ghose, and G.M. Crippen J. Comput. Chem. 7 1986 565
30. R. Bossio, S. Marcaccini, R. Pepino, and T. Torroba Synthesis 8 1993 783