Synthesis and in vitro evaluation of substituted pyrimido[5,4-d]pyrimidines as a novel class of Antimycobacterium tuberculosis agents

European Journal of Medicinal Chemistry

Volumn 45, Issue 7, 2010, Pages 3234-3239

  Bacelar, Ana H ^a   Carvalho, M Alice ^a   Proença, M Fernanda ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

Antimicrobial; Antimycobacterial activity; Pyrimido 5,4 d pyrimidine; Tuberculosis

Indexed keywords

ACETAMIDE DERIVATIVE; BENZAMIDE DERIVATIVE; BIS( 4 METHOXYPHENYL)TELLURIUM; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; ISONIAZID; N ( 4 IMINO 8 ( 4 METHOXYOPHENYLAMINO)PYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H)BENZAMIDE; N ( 4 IMINO 8 ( 4 METHOXYPHENYLAMINO)PYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL)FURAN 2 CARBOXAMIDE; N ( 4 IMINO 8 ( 4 METHOXYPHENYLAMINO)PYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL)ISONICOTINAMIDE; N ( 4 IMINO 8 (PHENYLAMINO)PYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL)ISONICOTINAMIDE; N ( 4 IMINO 8 (PHENYLAMINO)PYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H)BENZAMIDE; N ( 8 ( 4 CYANOPHENYLAMINO) 4 IMINOPYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL)BENZAMIDE; N ( 8 ( 4 CYANOPHENYLAMINO) 4 IMINOPYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL)ISONICOTINAMIDE; N ( 8 ( 4 FLUOROPHENYLAMINO) 4 IMINOPYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL)BENZAMIDE; N ( 8 ( 4 FLUOROPHENYLAMINO) 4 IMINOPYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL)ISONICOTINAMIDE; N ( 8 ANILINO 4 IMINOPYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL)ACETAMIDE; N [ 4 IMINO 8 (PHENYLAMINO)PYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL]FURAN 2 CARBOXAMIDE; N [ 4 IMINO 8 [( METHOXYPHENYL)AMINO]PYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL]ACETAMIDE; N [ 8 [( 4 CYANOPHENYL)AMINO] 4 IMINOPYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL]ACETAMIDE; N [ 8 [( 4 FLUOROPHENYL)AMINO] 4 IMINOPYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL]ACETAMIDE; N [ 8 [( 4 FLUOROPHENYL)AMINO] 4 IMINOPYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL]FURAN 2 CARBOXAMIDE; N [ 8 [( 4 FLUOROPHENYL)AMINO] 4 IMINOPYRIMIDO[ 5,4 D]PYRIMIDIN 3 (4H) YL]ISONICOTINAMIDE; NICOTINAMIDE DERIVATIVE; PYRAZINAMIDE; PYRIDINE DERIVATIVE; PYRIMIDO[5,4 D]PYRIMIDINE DERIVATIVE; RIFAMPICIN; STREPTOMYCIN; TELLURIUM DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; SUBSTITUTION REACTION;

EID: 77954349411     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.03.047     Document Type: Article

References (31)

1. C. Dye, Nat. Rev. Microbiol. 7 (2009) 81-87.
2. A.M. Ginsberg, Semin. Respir. Crit. Care Med 29 (2008) 552-559.
3. H.D. Showalter, W. Denny, Tuberculosis 88 (1) (2008) S3-S17.
4. H. Tomioka, Y. Tatano, K. Yasumoto, T. Shimizu, Expert Rev. Respir. Med. 2 (2008) 455-471.
5. R. Goldman, K.V. Plumley, B.E. Laughon, Infect. Disord. Drug Targets 7 (2007) 73-91.
6. L. Nguyen, C.J. Thompson, Trends Microbiol. 14 (2006) 304-312.
7. R. Shi, N. Itagaki, I. Sugawara, Mini-Reviews Med. Chem. 7 (2007) 1177-1185.
8. L. Ballell, R.A. Field, K. Duncan, R.J. Young, Antimicrob. Agents Chemother. (2005) 2153-2163.
9. A. Nayyar, R. Jain, Curr. Med. Chem. 12 (2005) 1873-1886.
10. R.P. Tangallapally, R. Yendapally, A.J. Daniels, R.E.B. Lee, Curr. Top. Med. Chem. 7 (2007) 509-526.
11. B.E. Laughon, Curr. Top. Med. Chem. 7 (2007) 463-473.
12. P.C. Srivastava, G.R. Revankar, R.K. Robins, R.J. Rousseau, J. Med. Chem. 24 (1981) 393-398.
13. P.D. Cook, D.A. Berry, US Patent 4,801,698; EP 257,488A2; Chem. Abstr.. 109:110861h.
14. Y.S. Sanghvi, S.B. Larson, S.S. Matsumoto, D.F. Nord, L.D. Smee, R.C. Willis, T. L. Avery, R.K. Robins, G.R. Revankar, J. Med. Chem. 32 (1989) 629-637.
15. T.E. Mabry, C.D. Jones, T.S. Chou, J.M. Colacino, G.B. Grindey, J.F. Worzalla, H. L. Pearce, Nucleosides Nucleotides 13 (1994) 1125-1133.
16. N.J. Curtin, H.C. Barlow, K.J. Bowman, A.H. Calvert, R. Davison, B.T. Golding, B. Huang, P.J. Loughlin, D.R. Newell, P.G. Smith, R.J. Griffin, J. Med. Chem. 47 (2004) 4905-4922.
17. J.S. Northen, F.T. Boyle, W. Clegg, N.J. Curtin, A.J. Edwards, R.J. Griffin, B. T. Golding, J. Chem. Soc. Perkin Trans. 1 (2002) 108-115.
18. G.W. Rewcastle, A.J. Bridges, D.W. Fry, J.R. Rubin, W.A. Denny, J. Med. Chem. 40 (1997) 1820-1826.
19. M. El-Araby, R.S. Pottorf, M.R. Player, Comb. Chem. High T. Scr. 7 (2004) 413-421.
20. G.W. Rewcastle, W.A. Denny, D.H. Showalter, Curr. Org. Chem. 4 (2000) 679-706.
21. A. Al-Azmi, J. Chem. Res. 8 (S) (2005) 530-534.
22. H.M. Berman, R.J. Rousseau, R.W. Mancuso, G.P. Kreishman, R.K. Robins, Tetrahedron Lett. 33 (1973) 3099-3101.
23. J.D. Westover, G.R. Revankar, R.K. Robins, R.D. Madsen, J.R. Orgden, J.A. North, R.W. Mancuso, R.J. Rousseau, E.L. Stephen, J. Med. Chem. 24 (1981) 941-946.
24. T.S. Rao, G.R. Revankar, Nucleosides Nucleotides 14 (1995) 1601-1612.
25. M.A. Carvalho, S. Esperança, T. Esteves, M.F. Proença, Eur. J. Org. Chem. (2007) 1324-1331.
26. A. Al-Azmi, B.L. Booth, R.A. Carpenter, M.A. Carvalho, E. Marrelec, R. G. Pritchard, M.F. Proença, J. Chem. Soc. Perkin Trans. 1 (2001) 2532-2537.
27. M.J. Alves, B.L. Booth, M.A. Carvalho, R.G. Pritchard, M.F. Proença, J. Heterocycl. Chem. 34 (1997) 739-743.
28. A. Ribeiro, M.A. Carvalho, M.F. Proença, Eur. J. Org. Chem. (2009) 4867-4872.
29. (a)L.A. Collins, S.G. Franzblau, Antimicrob. Agents Chemother. 41 (1997) 1004-1009
30. I. Orme, J. Secrist, S. Anathan, C. Kwong, J. Maddry, R. Reynolds, A. Poffenberger, M. Michael, L. Miller, J. Krahenbuh, L. Adams, A. Biswas, S. Franzblau, D. Rouse, D. Winfield, J. Brooks, Antimicrob. Agents Chemother. 45 (2001) 1943-1946
31. http:www.taacf.org (accessed 02.02.10).