Dihydropyrido[2,3-d]pyrimidines as a new class of antileishmanial agents

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 24, 2005, Pages 6678-6684

  Agarwal, Anu ^a   Ramesh, ^a   Ashutosh, ^a   Goyal, Neena ^a   Chauhan, Prem M S ^a   Gupta, Suman ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Dihydrofolate reductase; Dihydropyrido 2,3 d pyrimidine; Lieshmania; Uracil

Indexed keywords

4 (6 ACETYL 1,3,7 TRIMETHYL 2,4 DIOXO 1,2,3,4 TETRAHYDROPYRIDO[2,3 D]PYRIMIDIN 5 YL)BENZONITRILE; 4 (6 ACETYL 1,3,7 TRIMETHYL 2,4 DIOXO 1,2,3,4,5,8 HEXAHYDROPYRIDO[2,3 D]PYRIMIDIN 5 YL)BENZOIC ACID; 6 ACETYL 1,3,5,7 TETRAMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 1,3,7 TRIMETHYL 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 1,3,7 TRIMETHYL 2,4 DIOXO 1,2,3,4,5,8 HEXAHYDROPYRIDO[2,3 D]PYRIMIDINE 5 YLBENZONITRILE; 6 ACETYL 1,3,7 TRIMETHYL 5 (3 NITROPHENYL) 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 1,3,7 TRIMETHYL 5 (3,4,5 TRIMETHOXYPHENYL) 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 1,3,7 TRIMETHYL 5 (4 NITROPHENYL) 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 1,3,7 TRIMETHYL 5 (4 TOLYL) 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (3 METHOXYPHENYL) 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (3,4 DICHLOROPHENYL) 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (3,4 DIMETHOXYPHENYL) 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (3,4 DIMETHYLPHENYL) 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (4 CHLOROPHENYL) 1,3,7 TRIMETHYL 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (4 CHLOROPHENYL) 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (4 FLUOROPHENYL) 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (4 HYDROXYPHENYL) 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (4 ISOPROPYLPHENYL) 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (4 METHOXYPHENYL) 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 (4 METHOXYPHENYL)1,3,7 TRIMETHYL 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 FURAN 2 YL 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; 6 ACETYL 5 PHENYL 1,3,7 TRIMETHYL 5,8 DIHYDRO 1H PYRIDO[2,3 D]PYRIMIDINE 2,4 DIONE; ANTILEISHMANIAL AGENT; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INHIBITION KINETICS; NONHUMAN; PROMASTIGOTE;

ANIMALS; ANTIPROTOZOAL AGENTS; HYDROGEN; LEISHMANIA; MOLECULAR STRUCTURE; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 27644452545     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.07.043     Document Type: Article

References (52)

1. Tropical Disease Research: Progress 1999-2000; World Health Organization: Geneva, 2001
2. K.A. Werbovetz Curr. Med. Chem. 7 2000 835 860
3. D.R. Goldsmith, and C.M. Perry Drugs 64 2004 1905 1911
4. P.L. Olliaro, and A.D.M. Bryceson Parasitol. Today 9 1993 323 328
5. World Health Organization, Division of Control of Tropical Diseases, http://www.who.int/emc/diseases/leish/index.html.
6. R. Reithinger Emerg. Infect. Dis. 9 2003 727 729
7. A. Mcgregor Lancet 351 1998 575
8. J. Soto, B.A. Arana, J. Toledo, N. Rizzo, J.C. Vega, A. Diaz, M. Luz, M. Gutierre-Arboleda, J.D. Berman, K. Junge, J. Engel, and H. Sindermann Clin. Infect. Dis. 38 2004 1266 1272
9. R. Prasad, R. Kumar, B.P. Jaiswal, and U.K. Singh Indian J. Pediatr. 71 2004 143 144
10. H. Sangraula, K.K. Sharma, S. Rijal, S. Dwivedi, and S. Koirala J. Assoc. Physicians India 51 2003 686 690
11. P.B. Carvalho, M.A.G. Arribas, and E.I. Ferreira Braz. J. Pharm. Sci. 36 2000 69 96
12. G. Chakrabarti, A. Basu, P.P. Manna, S.B. Mahato, N.B. Mandal, and S.J. Bandyopadhyay Antimicrob. Chemother. 43 1999 359 366
13. S.A. Gamage, D.P. Figgit, S.J. Wojcik, R.K. Ralph, A. Ransijn, J. Maul, V. Yardley, D. Snowdon, S.L. Croft, and W.A. Denny J. Med. Chem. 40 1997 2634 2642
14. M.O. Khan, S.E. Austin, C. Chan, H. Yin, D. Marks, S.N. Vaghjiani, H. Kendrick, V. Yardley, S.L. Croft, and K.T. Douglas J. Med. Chem. 43 2000 3148 3156
15. H.B. Cottam, C.R. Petrie, P.A. McKranan, R.J. Goebel, N.K. Dalley, R.B. Davidson, and G.R. Revanker J. Med. Chem. 27 1984 1119 1127
16. A.M. Aronov, and M.H. Gelb Bioorg. Med. Chem. Lett. 8 1998 3505 3510
17. A. Mayence, J.J.V. Eynde, L. LeCour Jr, L.A. Walker, B.L. Tekwani, and T.L. Huang Eur. J. Med. Chem. 39 2004 47 553
18. H.D. Mello, A. Echevarria, A.M. Bernardino, M.C. Cavalheiro, and L.L. Leon J. Med. Chem. 47 2004 5427 5432
19. F. Delmas, A. Avellaneda, C.D. Giorgio, M. Robin, E.D. Clercq, P.T. David, and J.P. Galy Eur. J. Med. Chem. 39 2004 685 690
20. J.H. Robert, C. Sabourin, N. Alvare, S. Robert-Piessard, G. Le Baut, and P. Le Pape Eur. J. Med. Chem. 38 2003 711 718
21. A. Mäntyla, T. Garnier, J. Rautio, T. Nevalainen, J. Vepsälainen, A. Koskinen, S.L. Croft, and T. Järvinen J. Med. Chem. 47 2004 188 195
22. A. Mäntylä, J. Rautio, T. Nevalainen, J. Vepsälainen, R. Juvonen, H. Kendrick, T. Garnier, S.L. Croft, and T. Järvinen Bioorg. Med. Chem. 12 2004 3497 3502
23. Ashutosh, S. Gupta, Ramesh, S. Sundar, and N. Goyal Antimicrob. Agents and Chemother. 49 2005 3776
24. A. Mayence, J.J.V. Eynde, L. LeCour Jr, L.A. Walker, B.L. Tekwani, and T.L. Huang Eur. J. Med. Chem. 39 2004 547 553
25. M. Liu, P. Wilairat, S.L. Croft, A.L.C. Tand, and M.L. Goa Bioorg. Med. Chem. 11 2003 2729 2738
26. O. Kayser, A.F. Kiderlen, H. Laastsch, and S.L. Croft Acta Trop. 76 2000 131 138
27. M. Rabinovitch, and V. Zilberfarb Parasitology 96 1988 289
28. E. Del Olmo, M. Alves, J.L. Lopez, A. Inchaustti, G. Yalu, R.A. Arias de, and S.A. Feliano Bioorg. Med. Chem. Lett. 12 2002 659 662
29. S.L. Croft, D. Snowdon, and V.J. Yardley J. Antimicrob. Chemother. 38 1996 1041 1047
30. N. Avlonitis, E. Lekka, A. Detsi, M. Koufaki, T. Calogeropoulou, E. Scoulica, E. Siapi, I. Kyrikou, T. Mavromoustakos, A. Tsotinis, S.G. Grdadolnik, and A. Makriyannis J. Med. Chem. 46 2003 755 767
31. G. Bhattacharya, J. Herman, D. Delfý'n, M.M. Salem, T. Barszcz, M. Mollet, G. Riccio, R. Brun, and K.A. Werbovetz J. Med. Chem. 47 2004 1823 1832
32. M.A. Avery, K.M. Muraleedharan, P.V. Desai, A.K. Bandyopadhyaya, M.M. Furtado, and B.L. Tekwani J. Med. Chem. 46 2003 4244 4258
33. G. Lowe, A.S. Droz, T. Vilaivan, G.W. Weaver, L. Tweedale, J.M. Pratt, P. Rock, V. Yardley, and S.L. Croft J. Med. Chem. 42 1999 999 1006
34. Lunt, E.; Newton, C. G. Pyridodiazines and their benzo derivatives. In Comprehensive Heterocyclic Chemistry, Katritzky, A. R., Rees, C. W., Boulton, A. J., Mckillop, A., Eds.; Permgamon Press: Oxford, 1984; Vol. 3, pp 199, 232, 260-261
35. T.K. Bradshaw, and D.W. Hutchinson Chem. Soc. Rev. 6 1977 43
36. J. Quiroga, S. Cruz, B. Insuasty, and R. Abonia J. Het. Chem. 38 2001 53
37. A.J. Thakur, P. Saikia, D. Prajapati, and J.S. Sandhu Synlett 2001 1299 1301
38. M.-J. Perez-Perez, E.-M. Pretago, M.-L. Jimeno, and M.-J. Camarasa Synlett 2002 155 157
39. P. Bhuyan, R.C. Boruah, and J.S. Sandhu J. Org. Chem. 55 1990 568 571
40. C.E. Muller, U. Geis, J. Hipp, U. Schobert, W. Frobenius, M. Pawlowski, F. Suzuki, and J. Sandoval-Ramirez J. Med. Chem. 40 1997 4396 4405
41. R. Neal, and S. Croft J. Antimicrob. Chemother. 14 1984 463 475
42. B. Nare, J. Luba, L. Hardy, and S. Beverly Parasitology 114 1997 S101 S110
43. L. Hardy, W. Matthews, B. Nare, and S. Beverley Exp. Parasitol. 87 1997 157 169
44. A. Gangjee, A. Vasudevan, S.F. Queener, and R.L. Kisliuk J. Med. Chem. 39 1996 1438 1446
45. A. Gangjee, A. Vasudevan, S.F. Queener, and R.L. Kisluik J. Med. Chem. 38 1995 1778 1785
46. S.K. Srivastava, P.M.S. Chauhan, A.P. Bhaduri, N. Fatima, and R.K. Chatterjee J. Med. Chem. 43 2000 2275 2279
47. S.K. Srivastava, A. Agarwal, P.M.S. Chauhan, S.K. Agarwal, A.P. Bhaduri, S.N. Singh, N. Fatima, and R.K. Chatterjee J. Med. Chem. 42 1999 1667 1672
48. A. Agarwal, K. Srivastava, S.K. Puri, and P.M.S. Chauhan Bioorg. Med. Chem. Lett. 5 2005 531 533
49. A. Kumar, S. Sinha, and P.M.S. Chauhan Bioorg. Med. Chem. Lett. 12 2002 667 669
50. A. Agarwal, K. Srivastava, S.K. Puri, and P.M.S. Chauhan Bioorg. Med. Chem. Lett. 15 2005 1881 1883
51. S. Tiwari, P.M.S. Chauhan, A.P. Bhaduri, N. Fatima, and R.K. Chatterjee Bioorg. Med. Chem. Lett. 10 2000 1409 1412
52. A. Agarwal, and P.M.S. Chauhan Synth. Commun. 34 2004 4447 4461