Syntheses of new substituted triazino tetrahydroisoquinolines and β-carbolines as novel antileishmanial agents

European Journal of Medicinal Chemistry

Volumn 41, Issue 1, 2006, Pages 106-113

  Kumar, Arun ^a   Katiyar, Sanjay Babu ^a   Gupta, Suman ^a   Chauhan, Prem M S ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Carboline; Antileishmanial activity; Tetrahydroisoquinoline

Indexed keywords

1 (4 CHLOROPHENYL) 2 (4,6 DI MORPHOLIN 4YL [1,3,5] TRIAZIN 2YL) 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 (4,6 DI MOPHOLIN 4 YL [1,3,5] TRIAZIN 2 YL) 1 P TOLYL 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 (4,6 DI MORPHOLIN 4 YL [1,3,5] TRIAZIN 2YL) 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 (4,6 DI MORPHOLIN 4YL [1,3,5] TRIAZIN 2 YL) 1 P TOLYL 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 [4,6 BIS (4 METHYLPIPERAZIN 1 YL) [1,3,5] TRIAZIN 2 YL] 1 (4 CHLOROPHENYL 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 [4,6 BIS (4 METHYLPIPERAZIN 1 YL) [1,3,5] TRIAZIN 2 YL] 1 (4 CHLOROPHENYL) 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 [4,6 BIS (4 METHYLPIPERAZIN 1 YL) [1,3,5] TRIAZIN 2 YL] 1 P TOLYL 2,3,4,9 TETRAHYDRO 1 H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 [4,6 BIS (4 PHENYLPIPERAZIN 1 YL) [1,3,5] TRIAZIN 2 YL] 1 P TOLYL 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 [4,6 BIS (4 PHENYLPIPERAZIN 1 YL) [1,3,5]TRIAZIN 2 YL] 1 (4 CHLOROPHENYL) 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 [4,6 BIS (4 PHENYLPIPERAZIN LYL) [1,3,5] TRIAZIN 2YL ] 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 [4,6 BIS (4 PYRIDIN 2 YL PIPERAZIN 1 YL ) [1,3,5] TRIAZIN 2 YL] 1 (4 CHLOROPHENYL) 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 [4,6 BIS (4 PYRIDIN 2 YL PIPERAZIN 1 YL) [1,3,5] TRIAZIN 2 YL] 1 P TOLYL 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 [4,6 BIS (4 PYRIDIN 2 YL PIPERAZIN 1 YL) [1,3,5] TRIAZIN 2 YL] 1 P TOYL 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2 [4,6 BIS(4 PHENYLPIPERAZIN 1 YL) [1,3,5] TRIAZIN 2 YL] 1 P TOYL 2,3,4,9 TETRAHYDRO 1H BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; ANTILEISHMANIAL AGENT; BETA CARBOLINE DERIVATIVE; N,N DICYCLOHEXYL 6 (3,4 DIHYDRO 1H ISOQUINOLIN 2 YL [1,3,5] TRIAZINE 2,4 DIAMINE; QUINOLINE DERIVATIVE; TRIAZINO TETRAHYDROISOQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG INHIBITION; DRUG SYNTHESIS; IN VIVO STUDY; LEISHMANIA DONOVANI;

ANIMALS; ANTIPROTOZOAL AGENTS; CARBOLINES; CRICETINAE; INHIBITORY CONCENTRATION 50; LEISHMANIA DONOVANI; MESOCRICETUS; MOLECULAR STRUCTURE; PARASITIC SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROISOQUINOLINES; TRIAZINES;

EID: 33244494634     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejmech.2005.09.007     Document Type: Article

References (23)

1. World Health Organization Tropical Disease Research Progress 1975-1994. Highlights 1993-1994, UNDP/World Bank/ 1995 WHO Geneva
2. World Health Organization Fact sheet No. 116; World Health Organization 2000 Switzerland Geneva
3. E. Rosenthal, and P. Marty J. Postgrad. Med. 49 2003 61 68
4. S.L. Croft Trends Pharacol. Sci. 9 1988 376 381
5. J.D. Berman Rev. Infect. Dis. 10 1988 560 586
6. A.C. Smith, V. Yardlay, J. Rhodes, and S.L. Croft Antimicrob. Agents Chemother. 44 2000 1494 1498
7. C.P. Thakur, J.P. Debet, S. Narayan, and F. Pratlong Trans. R. Soc. Trop. Med. Hyg. 95 2001 187 189
8. G. Chakrabarti, A. Basu, P.P. Manna, S.B. Mahato, N.B. Mandal, and S. Bandyopadhyay J. Antimicrob. Chemother. 43 1999 359 366
9. 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
10. 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
11. J.L. Avila, M.A. Polegre, A. Avila, and R.K. Robins Comp. Biochem. Physiol. Part C: Comp. Pharmacology. 83 1986 285 289
12. 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
13. A.M. Aronov, and M.H. Gelb Bioorg. Med. Chem. Lett. 8 1998 3505 3510
14. 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
15. 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
16. 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
17. P.M.S. Chauhan, and S. Srivastava Curr. Med. Chem. 8 2001 1535 1542
18. P.M.S. Chauhan Drugs of the future 25 2000 481 488
19. S. Soerens, J. Sandrin, F. Ungemach, P. Mokry, G.S. Wu, E. Yamanaka, E. Hutchins, M. DiPierro, and J.M. Cook J. Org. Chem. 44 1979 535 545
20. J. Sandrin, D. Sorens, and J.M. Cook Heterocycl. 4 1976 1249 1255
21. S. Beveridge R.J. Schnitzer F.I. Hanoking Experimental Chemotherapy, 1 1963 257 280
22. S. Bhatnagar, P.Y. Guru, J.C. Katiyar, R. Srivastava, A. Mukherjee, M.S. Akhtar, M. Seth, and A.P. Bhaduri Indian J. Med. Res. 89 1989 439 444
23. S. Gupta, S. Tiwari, A.P. Bhaduri, and G.K. Jain Acta Trop. 84 2002 165 173