Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 9, 2005, Pages 3249-3261

  Chiyanzu, Idan ^a   Clarkson, Cailean ^b   Smith, Peter J ^b   Lehman, Julie ^c   Gut, Jiri ^c   Rosenthal, Philip J ^c   Chibale, Kelly ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Aminoquinolines; Anti plasmodial activity; Falcipain 2; Isatins; Malaria; Mannich bases; Plasmodium falciparum; Thiosemicarbazones

Indexed keywords

5 CHLORO N 1 [2 (7 CHLOROQUINOLIN 4' YLAMINO)ETHYL] 1H INDOLE 2,3 DIONE; CYSTEINE PROTEINASE; FALCIPAIN 2; ISATIN DERIVATIVE; N 1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 1H INDOLE 2,3 DIONE 3 THIOSEMICARBAZONE; N 1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 5 CHLORO 1H INDOLE 2,3 DIONE 3 THIOSEMICARBAZONE; N 1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 5 METHYL 1H INDOLE 2,3 DIONE; N 1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 5 METHYL 1H INDOLE 2,3 DIONE 3 THIOSEMICARBAZONE; N 1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 5,7 DIMETHYL 1H INDOLE 2,3 DIONE; N 1 [2 (7 CHLOROQUINOLIN 4' YLAMINO)ETHYL] 1H INDOLE 2,3 DIONE; N 1 [4 (7 CHLOROQUINOLIN 4 YL)PIPERAZIN 1 YLMETHYL] 1H INDOLE 2,3 DIONE; N 1 [4 (7 CHLOROQUINOLIN 4 YL)PIPERAZIN 1 YLMETHYL] 5 BROMO 1H INDOLE 2,3 DIONE 3 THIOSEMICARBAZONE; N 1 [4 (7 CHLOROQUINOLIN 4 YL)PIPERAZIN 1 YLMETHYL] 5 CHLORO 1H INDOLE 2,3 DIONE; N 1 [4 (7 CHLOROQUINOLIN 4 YL)PIPERAZIN 1 YLMETHYL] 5 CHLORO 1H INDOLE 2,3 DIONE 3 THIOSEMICARBAZONE; N 1 [4 (7 CHLOROQUINOLIN 4 YL)PIPERAZIN 1 YLMETHYL] 5 FLUORO 1H INDOLE 2,3 DIONE; N 1 [4 (7 CHLOROQUINOLIN 4 YL)PIPERAZIN 1 YLMETHYL] 5 IODO 1H INDOLE 2,3 DIONE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; IC 50; IN VITRO STUDY; NONHUMAN; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION;

EID: 16244370734     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.02.037     Document Type: Article

References (33)

1. World Health Organisation Fact Sheet No. 94. Revised Oct. WHO information. http://www.int/inf~fs/en/fact094.html 1998
2. Lima, P. D. C.; Barreiro, E. J. Avery, M. A. Abstracts of Papers, 223rd ACS National Meeting, Orlando, FL, USA, April 7-11, 2002; American Chemical Society: Washington, DC, 2002; MEDI-176
3. M. Flipo, I. Florent, P. Grellier, C. Sergheraert, and R. Deprez-Poulain Bioorg. Med. Chem. Lett. 13 2003 2659
4. S. Romeo, M. Dell'Agli, S. Parapini, L. Rizzi, G. Galli, M. Mondani, A. Sparatore, D. Taramelli, and E. Bosisio Bioorg. Med. Chem. Lett. 14 2004 2931
5. C. Biot, J. Dessolin, and E. Davioud-Charvet Redox Rep. 8 2003 280
6. E. Davioud-Charvet, S. Delarue, C. Biot, B. Schwobel, C.C. Boehme, A. Mussigbrodt, L. Maes, C. Sergheraert, P. Grellier, R.H. Schirmer, and K. Becker J. Med. Chem. 44 2001 4268
7. C.C. Musonda, D. Taylor, J. Lehman, J. Gut, P.J. Rosenthal, and K. Chibale Bioorg. Med. Chem. Lett. 14 2004 3901
8. F. Lecaille, J. Kaleta, and D. Bromme Chem. Rev. 102 2002 4459
9. M. Sajid, and J.H. McKerrow Mol. Biochem. Parasitol. 120 2002 1
10. R.W. Marquis Ann. Rep. Med. Chem. 35 2000 309
11. I. Chiyanzu, E. Hansell, J. Gut, P.J. Rosenthal, J.H. McKerrow, and K. Chibale Bioorg. Med. Chem. Lett. 13 2003 3527
12. P.J. Rosenthal, P.S. Sijwali, A. Singh, and B.R. Shenai Curr. Pharm. Des. 8 2002 1659
13. T.J. Egan Drug Des. Rev.-Online 1 2004 93
14. C. Biot Curr. Med. Chem.-Anti-Infect. Agents 3 2004 135
15. K. Chibale, J.R. Moss, M. Blackie, D. van Schalkwyk, and P.J. Smith Tetrahedron Lett. 41 2000 6231
16. R.G. Ridley, W. Hofheinz, H. Matile, C. Jaquet, A. Dorn, R. Masciadri, S. Jolidon, W.F. Richter, A. Guenzi, M.-A. Girometta, H. Urwyler, W. Huber, S. Thaithong, and W. Peters Antimicrob. Agents Chemother. 40 1996 1846
17. D. De, F.M. Krogstad, L.D. Byers, and D.J. Krogstad J. Med. Chem. 42 1998 4918
18. X. Du, C. Guo, E. Hansell, P.S. Doyle, C.R. Caffrey, T.P. Holler, J.H. McKerrow, and F.E. Cohen J. Med. Chem. 45 2002 2695
19. T.J. Egan, R. Hunter, C.H. Kaschula, H.M. Marques, A. Misplon, and J. Walden J. Med. Chem. 43 2000 283
20. B. Pradines, J.M. Rolain, F. Ramiandrasoa, T. Fusai, J. Mosnier, C. Rogier, W. Daries, E. Baret, G. Kunesch, J. Le Bras, and D. Parzy J. Antimicrob. Chemother. 50 2002 177
21. L. Lundt, and R. Madsen Synthesis 1992 1129
22. A. Semenov, J.E. Olson, and P.J. Rosenthal Antimicrob. Agents Chemother. 42 1998 2254
23. W. Trager, and J. Jensen Science 193 1976 673
24. M.T. Makler, R.C. Piper, and W.K. Milhous Parasitol. Today 14 1998 376
25. P.S. Sijwali, K. Kato, K.B. Seydel, J. Gut, J. Lehman, M. Klemba, D.E. Goldberg, L.H. Miller, and P.J. Rosenthal Proc. Natl. Acad. Sci. U.S.A. 101 2004 8721
26. D.C. Greenbaum, A. Baruch, M. Grainger, Z. Bozdech, K.F. Medzihradszky, J. Engel, J. Derisi, A.A. Holder, and M. Bogyo Science 298 2002 2002
27. S. Eksi, B. Czesny, D.C. Greenbaum, M. Bogyo, and K.C. Williamson Mol. Microbiol. 53 2004 243
28. D.C. Greenbaum, Z. Mackey, E. Hansell, P. Doyle, J. Gut, C.R. Caffrey, J. Lehman, P.J. Rosenthal, J.H. McKerrow, and K. Chibale J. Med. Chem. 47 2004 3212
29. D. Sweeney, M.L. Raymer, and T.D. Lockwood Biochem. Pharmacol. 66 2003 663
30. K.K. Eggleson, K.L. Duffin, and D.E. Goldberg J. Biol. Chem. 274 1999 411
31. A.M. Moormann, P.A. Hossler, and S.R. Meshnick Mol. Biochem. Parasitol. 98 1999 283
32. G. Fritsch, G. Sawatzki, J. Treumer, A. Jung, and D.T. Spira Exp. Parasitol. 63 1997 1
33. S.V. Rajendra, and L.W. Wobles J. Med. Chem. 10 1967 972