Synthesis of non-purine analogs of 6-aryl-9-benzylpurines, and their antimycobacterial activities. Compounds modified in the imidazole ring

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 20, 2010, Pages 7274-7282

  Khoje, Abhijit Datta ^a   Kulendrn, Aisvareya ^a   Charnock, Colin ^b   Wan, Baojie ^c   Franzblau, Scott ^c   Gundersen, Lise Lotte ^a  

^a UNIVERSITY OF OSLO   (Norway)

^b OSLO METROPOLITAN UNIVERSITY   (Norway)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

Heterocycles; Resistant strains; Tuberculosis

Indexed keywords

2 CHLORO 4 (2 FURYL) 7 (4 METHOXYBENZYL) 7H PYRROLO[2,3 D]PYRIMIDINE; 2 CHLORO 7 (4 METHOXYBENZYL) 4 (2 THIENYL) 7H PYRROLO[2,3 D]PYRIMIDINE; 4 (2 FURYL) 1 (4 METHOXYBENZYL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 4 (2 FURYL) 2 METHOXY 7 (4 METHOXYBENZYL) 7H PYRROLO[2,3 D]PYRIMIDINE; 4 (2 FURYL) 7 (4 METHOXYBENZYL) 5 METHYL 5H PYRROLO[3,2 D]PYRIMIDINE; 4 (2 FURYL) 7 (4 METHOXYBENZYL) 7H PYRROLO[2,3 D]PYRIMIDINE; 6,7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO[2,1 B][1,3]OXAZINE; 7 (2 FURYL)[3 (4 METHOXYBENZYLAMINO)] 3H [1,2,3]TRIAZOLO[4,5 D]PYRIMIDINE; 7 (4 METHOXYBENZYL) 4 (2 THIENYL) 7H PYRROLO[2,3 D]PYRIMIDINE; [4 (2 FURYL) 5 [(TRIISOPROPYLSILYLOXY)METHYL] 5H PYRROLO[3,2 D]PYRIMIDIN 7 YL](4 METHOXYPHENYL)METHANONE; [4 (2 FURYL) 5 METHYL 5H PYRROLO[3,2 D]PYRIMIDIN 7 YL](4 METHOXYPHENYL)METHANONE; [4 (2 FURYL) 5H PYRROLO[3,2 D]PYRIMIDIN 7 YL](4 METHOXYPHENYL)METHANONE; ANTIMYCOBACTERIAL AGENT; CLOFAZIMINE; IMIDAZOLE; ISONIAZID; KANAMYCIN; MONOFLOXACIN; PURINE DERIVATIVE; RIFAMPICIN; STREPTOMYCIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; STAPHYLOCOCCUS AUREUS;

ANIMALS; ANTI-BACTERIAL AGENTS; CERCOPITHECUS AETHIOPS; DRUG RESISTANCE, BACTERIAL; IMIDAZOLES; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; PURINES; VERO CELLS;

ESCHERICHIA COLI; MAMMALIA; MYCOBACTERIUM TUBERCULOSIS; MYCOBACTERIUM TUBERCULOSIS H37RV; STAPHYLOCOCCUS AUREUS;

EID: 77957574197     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.08.016     Document Type: Article

References (42)

1. A.K. Bakkestuen, L.-L. Gundersen, G. Langli, F. Liu, and J.M.J. Nolsøe Bioorg. Med. Chem. Lett. 10 2000 1207
2. L.-L. Gundersen, J. Nissen-Meyer, and B. Spilsberg J. Med. Chem. 45 2002 1383
3. G. Andresen, L.-L. Gundersen, J. Nissen-Meyer, F. Rise, and B. Spilsberg Bioorg. Med. Chem. Lett. 12 2002 567
4. A.K. Bakkestuen, L.-L. Gundersen, and B.T. Utenova J. Med. Chem. 48 2005 2710
5. M. Brændvang, and L.-L. Gundersen Bioorg. Med. Chem. 13 2005 6360
6. M. Brændvang, and L.-L. Gundersen Bioorg. Med. Chem. 15 2007 7144
7. M. Brændvang, V. Bakken, and L.-L. Gundersen Bioorg. Med. Chem. 17 2009 6512
8. See for instance: Global Alliance for TB Drug Development, The Need for New TB Drugs, 2005, www.tballiance.org.
9. V. Bhowruth, L.G. Dover, and G.S. Besra Prog. Med. Chem. 45 2007 169
10. M. Brændvang, and L.-L. Gundersen Tetrahedron Lett. 48 2007 3057
11. M. Brændvang, C. Charnock, and L.-L. Gundersen Bioorg. Med. Chem. Lett. 19 2009 3297
12. P.O. Miranda, and L.-L. Gundersen Arch. Pharm. Chem. Life Sci. 343 2010 40
13. M.L. Read, M. Brændvang, P.O. Miranda, and L.-L. Gundersen Bioorg. Med. Chem. 18 2010 3885
14. J.L. Kelley, R.G. Davis, E.W. McLean, R.C. Glen, F.E. Soroko, and B.R. Cooper J. Med. Chem. 38 1995 3884
15. S.B. Sobolov, J. Sun, and B.A. Cooper Tetrahedron Lett. 39 1998 5685
16. S. Niwas, P. Chand, V.P. Pathak, and J.A. Montgomery J. Med. Chem. 37 1994 2477
17. T.L. Smalley Jr., A.J. Peat, J.A. Boucheron, S. Dickerson, D. Garrido, F. Preugschat, S.L. Schweiker, S.A. Thomson, and T.Y. Wang Bioorg. Med. Chem. Lett. 16 2006 2091
18. G.B. Evans, R.H. Furneaux, A. Lewandowicz, V.L. Schramm, and P.C. Tyler J. Med. Chem. 46 2003 3412
19. T. Semeraro, C. Mugnaini, and F. Corelli Tetrahedron Lett. 49 2008 5965
20. J.D. Rose, J.A. Secrist III, and J.A. Montgomery Nucleosides, Nucleotides 18 1999 2443
21. G.B. Evans, R.H. Furneaux, T.L. Hutchison, H.S. Kezar, P.E. Morris, V.L. Schramm, and P.C. Tyler J. Org. Chem. 66 2001 5723
22. M. Otmar, M. Masojidkova, I. Votruba, and A. Holy Bioorg. Med. Chem. 12 2004 3189
23. H. Shih, H.B. Cottam, and D.A. Carson Chem. Pharm. Bull. 50 2002 364
24. G.B. Evans, R.H. Furneaux, H. Hausler, J.S. Larsen, and P.C. Tyler J. Org. Chem. 69 2004 2217
25. H.S. Kezar III, J.M. Kilpatrick, D. Phillips, D. Kellogg, J. Zhang, and P.E. Morris Jr. Nucleosides, Nucleotides, Nucleic Acids 24 2005 1817
26. K. Clinch, G.B. Evans, G.W.J. Fleet, R.H. Furneaux, S.W. Johnson, D.H. Lenz, S.P.H. Mee, P.R. Rands, V.L. Schramm, E.A. Taylor Ringia, and P.C. Tyler Org. Biomol. Chem. 4 2006 1131
27. R.J. Kloetzing, A. Krasovskiy, and P. Knochel Chem. Eur. J. 13 2007 215
28. T. Benneche, L.-L. Gundersen, and K. Undheim Acta Chem. Scand. B 42 1988 384
29. G. Andresen, A.B. Eriksen, B. Dalhus, L.-L. Gundersen, and F. Rise J. Chem. Soc., Perkin Trans. 1 2001 1662
30. G. Andresen, L.-L. Gundersen, and F. Rise ARCIVOC 2001 35
31. M.A. Zajac, and E. Vedejs Org. Lett. 6 2004 237
32. L.-L. Gundersen, T. Benneche, and K. Undheim Acta Chem. Scand. 43 1989 706
33. M. Shindo, T. Sugioka, Y. Umaba, and K. Shishido Tetrahedron Lett. 45 2004 8863
34. S. Pitsch, P.A. Weiss, X. Wu, D. Ackermann, and T. Honegger Helv. Chim. Acta 82 1999 1753
35. S. Pitsch, P.A. Weiss, L. Jenny, A. Stutz, and X. Wu Helv. Chim. Acta 84 2001 3773
36. L.A. Collins, and S.G. Franzblau Antimicrob. Agents Chemother. 41 1997 1004
37. K. Falzari, Z. Zhu, D. Pan, H. Liu, P. Hongmanee, and S.G. Franzblau Antimicrob. Agents Chemother. 49 2005 1447
38. C.K. Stover, P. Warrener, D.R. VanDevandter, D.R. Sherman, T.M. Arain, M.H. Langhorne, S.W. Anderson, J.A. Towell, Y. Yuan, D.N. McMurray, B.N. Kreiswirth, C.E. Barry, and W.R. Baker Nature 405 2000 962
39. S.H. Cho, S. Warit, B. Wan, C.H. Hwang, G.F. Pauli, and S.G. Franzblau Antimicrob. Agents Chemother. 51 2007 1380
40. A. Vik, E. Hedner, C. Charnock, Ø. Samuelsen, R. Larsson, L.-L. Gundersen, and L. Bohlin J. Nat. Prod. 69 2006 381
41. Kuzmich, D.; Disalvo, D.; Razavi, H. PCT Int. Appl. WO 2008070507, 2008, 273pp.
42. Vaisburg, A.; William, S.; Raeppel, F.; Saavedra, O. M.; Berstein, N.; Granger, M.-C.; Zhan, L. PCT Int. Appl. WO 2006010264, 2006, 283pp.