A study of the effects of substituents on the selectivity of the binding of N-arylaminomethylene malonate inhibitors to DHODH

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 3, 2010, Pages 1284-1287

  Cowen, Deborah ^a   Bedingfield, Paul ^a   McConkey, Glenn A ^a   Fishwick, Colin W G ^a   Johnson, A Peter ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

DHODH; Molecular modelling; Plasmodium falciparum

Indexed keywords

ANTIMALARIAL AGENT; DIHYDROOROTATE DEHYDROGENASE; DIHYDROOROTATE DEHYDROGENASE INHIBITOR; HYDROGEN; N ARYLAMINOMETHYLENE MALONATE INHIBITOR; OXYGEN; UBIQUINONE; UNCLASSIFIED DRUG; ANILINE DERIVATIVE; HYDROXYBUTYRIC ACID; MALONIC ACID; MALONIC ACID DERIVATIVE; OXIDOREDUCTASE; PROTEIN BINDING; TERIFLUNOMIDE;

ANTIMALARIAL ACTIVITY; ARTICLE; CHEMICAL BINDING; DRUG BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; NONHUMAN; PLASMODIUM; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECTS; HUMAN; METABOLISM; PHYSIOLOGY; PLASMODIUM FALCIPARUM; RAT;

PLASMODIUM FALCIPARUM;

ANILINE COMPOUNDS; ANIMALS; HUMANS; HYDROXYBUTYRATES; MALONATES; OXIDOREDUCTASES ACTING ON CH-CH GROUP DONORS; PLASMODIUM FALCIPARUM; PROTEIN BINDING; RATS;

EID: 74049165055     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.11.079     Document Type: Article

References (30)

1. World Health Organisation, Guidelines for the Treatment of Malaria.
2. World Health Organisation Malaria Factsheet.
3. Tuteja R. FEBS J. 274 (2007) 4670
4. Newton P., and White N. Annu. Rev. Med. 50 (1999) 179
5. Reyes R., Rathod P., Sanchez D., Mrema J., Rieckmann K., and Heidrich H. Mol. Biochem. Parasitol. 5 (1982) 275
6. Gutteridge W., and Trigg P. J. Protozool. 17 (1970) 89
7. Heikkila T., Thirumalairajan S., Davies M., Parsons M.R., McConkey A.G., Fishwick C.W.G., and Johnson A.P. Bioorg. Med. Chem. Lett. 16 (2006) 88
8. Boa A.N., Canavan S.P., Hirst P.R., Ramsey C., Stead A.M.W., and McConkey A.G. Bioorg. Med. Chem. 13 (2005) 1945
9. Yeates C.L., Batchelor J.F., Capon E.C., Cheesman N.J., Fry M., Hudson A.T., Pudney M., Trimming H., Woolven J., Bueno J.M., Chicarro J., Fernandez E., Fiandor J.M., Gargolla-Viola D., Gomez de las Heras F., Herreros E., and Leon M.L. J. Med. Chem. 51 (2008) 2845
10. Gujjar R., Marwaha A., El Mazouni F., White J., White K.L., Creason S., Shackleford D.M., Baldwin J., Charman W.N., Buckner F.S., Charman S., Rathod P.K., and Phillips M.A. J. Med. Chem. 52 (2009) 1864
11. Davies M., Heikkila T., McConkey G.A., Fishwick C.W.G., Parsons M.A., and Johnson A.P. J. Med. Chem. 52 (2009) 2683
12. Heikkila T., Ramsey C., Davies M., Galtier C., Stead A.M.W., Johnson A.P., Fishwick C.W.G., Boa A.N., and McConkey G.A. J. Med. Chem. 50 (2007) 186
13. Malmquist N.A., Baldwin J., and Phillips M.A. J. Biol. Chem. 282 (2007) 12678
14. Neidhardt E.A., Punreddy S.R., McLean J.E., Hedstrom L., and Grossman T.H. J. Mol. Microbiol. Biotechnol. 1 (1999) 183
15. Marcinkeviciene J., Jiang W., Locke G., Kopcho L.M., Rogers M.J., and Copeland R.A. Arch. Biochem. Biophys. 377 (2000) 178
16. Hines V., and Johnston M. Biochemistry 28 (1989) 1222
17. Bjornberg O., Jordan D.B., Palfey A.B., and Jensen K.F. Arch. Biochem. Biophys. 391 (2001) 286
18. Hurt D.E., Widom J., and Clardy J. Acta Crystallogr., Sect. D 62 (2006) 312
19. Copeland R.A., Marcinkeviciene J., Haque T.S., Kopcho L.M., Jiang W., Wang K., Ecret L.D., Sizemore C., Amsler K.A., Foster L., Tadesse S., Combs A.P., Stern A.M., Trainor G.L., Slee A., Rogers A.M., and Hobbs F. J. Biol. Chem. 275 (2000) 33373
20. Marcinkeviciene J., Rogers M.J., Kopcho L., Jiang W., Wang K., Murphy D.J., Lippy J., Link S., Chung T.D., Hobbs F., Haque T., Trainor G.L., Slee A., Stern A.M., and Copeland R.A. Biochem. Pharmacol. 60 (2000) 339
21. Patel V., Booker M., Kramer M., Ross L., Celatka C.A., Kennedy L.M., Dvorin J.D., Duraisingh M.T., Sliz P., Wirth D.F., and Clardy J. J. Biol. Chem. 283 (2008) 35078
22. Leban J., Kralik M., Mies J., Baumgartner R., Gassen M., and Tasler S. Bioorg. Med. Chem. Lett. 16 (2006) 267
23. Phillips M.A., Ramesh G., Malmquist N.A., White J., Mazouni F.E., Baldwin J., and Rathod P.K. J. Med. Chem. 51 (2008) 3649
24. Kobayashi K., Nakashima A., Nagata H., Nakajima H., Yamaguchi K., Sato S., and Miki I. Inflamm. Res. 50 (2001) 24
25. Kerwin M.S. J. Am. Chem. Soc. 127 (2005) 8899
26. Zsoldos Z., Reid D., Simon A., Sadjad S.B., and Johnson A.P. J. Mol. Graphics. Modell. 26 (2007) 198
27. Morris G.M., Goodsell D.S., Huey R., and Olson A.J. J. Comput. Mol. Des. 10 (1996) 293
28. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639
29. Huey R., Morris G.M., Olson A.J., and Goodsell D.S. J. Comput. Chem. 28 (2007) 1145
30. Baumgartner R., Walloschek M., Kralik M., Gotschlich A., Tasler S., Mies J., and Leban J. J. Med. Chem. 49 (2006) 1239