Synthesis and evaluation of α-thymidine analogues as novel antimalarials

Journal of Medicinal Chemistry

Volumn 55, Issue 24, 2012, Pages 10948-10957

  Cui, Huaqing ^a,b   Carrero Lérida, Juana ^b   Silva, Ana P G ^c   Whittingham, Jean L ^c   Brannigan, James A ^c   Ruiz Pérez, Luis M ^b   Read, Kevin D ^a   Wilson, Keith S ^c   González Pacanowska, Dolores ^b   Gilbert, Ian H ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

^b INSTITUTO DE PARASITOLOGÍA Y BIOMEDICINA LÓPEZ NEYRA   (Spain)

^c UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 TRIFLUOROMETHYL 4 CHLORO PHENYL UREA ALPHA THYMIDINE; ANTIMALARIAL AGENT; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CRYSTAL STRUCTURE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN;

ANTIMALARIALS; BLOOD PROTEINS; CELL LINE; CRYSTALLOGRAPHY, X-RAY; HUMANS; LIGANDS; MICROSOMES, LIVER; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NUCLEOSIDE-PHOSPHATE KINASE; PLASMODIUM FALCIPARUM; PROTEIN BINDING; PROTOZOAN PROTEINS; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; THIOUREA; THYMIDINE; UREA;

EID: 84871654541     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301328h     Document Type: Article

References (29)

1. Kilama, W.; Ntoumi, F. Malaria: a research agenda for the eradication era Lancet 2009, 374, 1480-1482
2. Gelb, M. H.; Hol, W. G. J. Parasitology-Drugs to combat tropical protozoan parasites Science 2002, 297, 343-344 (Pubitemid 34790750)
3. Geels, M. J.; Imoukhuede, E. B.; Imbault, N.; van Schooten, H.; McWade, T.; Troye-Blomberg, M.; Dobbelaer, R.; Craig, A. G.; Leroy, O. European Vaccine Initiative: lessons from developing malaria vaccines Expert Rev. Vaccines 2011, 10, 1697-1708
4. Cui, H. Q.; Ruda, G. F.; Carrero-Lerida, J.; Ruiz-Perez, L. M.; Gilbert, I. H.; Gonzalez-Pacanowska, D. Exploring new inhibitors of Plasmodium falciparum purine nucleoside phosphorylase Eur. J. Med. Chem. 2010, 45, 5140-5149
5. Cui, H. Q.; Ruiz-Perez, L. M.; Gonzalez-Pacanowska, D.; Gilbert, I. H. Potential application of thymidylate kinase in nucleoside analogue activation in Plasmodium falciparum Bioorg. Med. Chem. 2010, 18, 7302-7309
6. Gardner, M. J.; Hall, N.; Fung, E.; White, O.; Berriman, M.; Hyman, R. W.; Carlton, J. M.; Pain, A.; Nelson, K. E.; Bowman, S.; Paulsen, I. T.; James, K.; Eisen, J. A.; Rutherford, K.; Salzberg, S. L.; Craig, A.; Kyes, S.; Chan, M. S.; Nene, V.; Shallom, S. J.; Suh, B.; Peterson, J.; Angiuoli, S.; Pertea, M.; Allen, J.; Selengut, J.; Haft, D.; Mather, M. W.; Vaidya, A. B.; Martin, D. M. A.; Fairlamb, A. H.; Fraunholz, M. J.; Roos, D. S.; Ralph, S. A.; McFadden, G. I.; Cummings, L. M.; Subramanian, G. M.; Mungall, C.; Venter, J. C.; Carucci, D. J.; Hoffman, S. L.; Newbold, C.; Davis, R. W.; Fraser, C. M.; Barrell, B. Genome sequence of the human malaria parasite Plasmodium falciparum Nature 2002, 419, 498-511
7. Reyes, P.; Rathod, P. K.; Sanchez, D. J.; Mrema, J. E. K.; Rieckmann, K. H.; Heidrich, H. G. Enzymes of purine and pyrimidine metabolism from the human malaria, Plasmodium-falciparum Mol. Biochem. Parasitol. 1982, 5, 275-290
8. Sherman, I. W. Malaria: Parasite Biology, Pathogenesis and Protection; ASM Press: Washington, DC, 1998.
9. Anderson, A. C. Targeting DHFR in parasitic protozoa Drug Discovery Today 2005, 10, 121-128 (Pubitemid 40247810)
10. Booker, M. L.; Bastos, C. M.; Kramer, M. L.; Barker, R. H.; Skerlj, R.; Sidhu, A. B.; Deng, X. Y.; Celatka, C.; Cortese, J. F.; Bravo, J. E. G.; Llado, K. N. C.; Serrano, A. E.; Angulo-Barturen, I.; Jimenez-Diaz, M. B.; Viera, S.; Garuti, H.; Wittlin, S.; Papastogiannidis, P.; Lin, J. W.; Janse, C. J.; Khan, S. M.; Duraisingh, M.; Coleman, B.; Goldsmith, E. J.; Phillips, M. A.; Munoz, B.; Wirth, D. F.; Klinger, J. D.; Wiegand, R.; Sybertz, E. Novel inhibitors of Plasmodium falciparum dihydroorotate dDehydrogenase with Aanti-malarial activity in the mouse model J. Biol. Chem. 2010, 285, 33054-33064
11. Kandeel, M.; Ando, T.; Kitamura, Y.; Abdel-Aziz, M.; Kitade, Y. Mutational, inhibitory and microcalorimetric analyses of Plasmodium falciparum TMP kinase. Implications for drug discovery Parasitology 2009, 136, 11-25
12. Whittingham, J. L.; Carrero-Lerida, J.; Brannigan, J. A.; Ruiz-Perez, L. M.; Silva, A. P. G.; Fogg, M. J.; Wilkinson, A. J.; Gilbert, I. H.; Wilson, K. S.; Gonzalez-Pacanowska, D. Structural basis for the efficient phosphorylation of AZT-MP (3′-azido-3′-deoxythymidine monophosphate) and dGMP by Plasmodium falciparum type I thymidylate kinase Biochem. J. 2010, 428, 499-509
13. Lavie, A.; Ostermann, N.; Brundiers, R.; Goody, R. S.; Reinstein, J.; Konrad, M.; Schlichting, I. Structural basis for efficient phosphorylation of 3 ′-azidothymidine monophosphate by Escherichia col i thymidylate kinase Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 14045-14050
14. Ostermann, N.; Schlichting, I.; Brundiers, R.; Konrad, M.; Reinstein, J.; Veit, T.; Goody, R. S.; Lavie, A. Insights into the phosphoryltransfer mechanism of human thymidylate kinase gained from crystal structures of enzyme complexes along the reaction coordinate Structure 2000, 8, 629-642 (Pubitemid 30409315)
15. Lavie, A.; Konrad, M.; Brundiers, R.; Goody, R. S.; Schlichting, I.; Reinstein, J. Crystal structure of yeast thymidylate kinase complexed with the bisubstrate inhibitor P-1-(5′-adenosyl) P-5-(5′-thymidyl) pentaphosphate (TP(5)A) at 2.0 Å resolution: Implications for catalysis and AZT activation Biochemistry 1998, 37, 3677-3686 (Pubitemid 28162922)
16. Van Daele, I.; Munier-Lehmann, H.; Froeyen, M.; Balzarini, J.; Van Calenbergh, S. Rational design of 5′-thiourea-substituted alpha-thymidine analogues as thymidine monophosphate kinase inhibitors capable of inhibiting mycobacterial growth J. Med. Chem. 2007, 50, 5281-5292 (Pubitemid 350057840)
17. Topalis, D.; Collinet, B.; Gasse, C.; Dugue, L.; Balzarini, J.; Pochet, S.; Deville-Bonne, D. Substrate specificity of vaccinia virus thymidylate kinase FEBS J. 2005, 272, 6254-6265 (Pubitemid 41815614)
18. McNicholas, S.; Potterton, E.; Wilson, K. S.; Noble, M. E. M. Presenting your structures: the CCP4mg molecular-graphics software Acta Crystallogr. D 2011, 67, 386-394
19. Van Daele, I.; Munier-Lehmann, H.; Hendrickx, P. M. S.; Marchal, G.; Chavarot, P.; Froeyen, M.; Qing, L.; Martins, J. C.; Van Calenbergh, S. Synthesis and biological evaluation of bicyclic nucleosides as inhibitors of M-tuberculosis thymidylate kinase ChemMedChem 2006, 1, 1081-1090 (Pubitemid 44622249)
20. Familiar, O.; Munier-Lehmann, H.; Negri, A.; Gago, F.; Douguet, D.; Rigouts, L.; Hernandez, A. I.; Camarasa, M. J.; Perez-Perez, M. J. Exploring acyclic nucleoside analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase ChemMedChem 2008, 3, 1083-1093
21. Pochet, S.; Dugue, L.; Labesse, G.; Delepierre, M.; Munier-Lehmann, H. Comparative study of purine and pyrimidine nucleoside analogues acting on the thymidylate kinases of Mycobacterium tuberculosis and of humans ChemBiochem 2003, 4, 742-747 (Pubitemid 37010599)
22. Van Poecke, S.; Munier-Lehmann, H.; Helynck, O.; Froeyen, M.; Van Calenbergh, S. Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase Bioorg. Med. Chem. 2011, 19, 7603-7611
23. Balzarini, J.; Van Daele, I.; Negri, A.; Solaroli, N.; Karlsson, A.; Liekens, S.; Gago, F.; Van Calenbergh, S. Human mitochondrial thymidine kinase is selectively inhibited by 3 ′-thiourea derivatives of beta-thymidine: identification of residues crucial for both inhibition and catalytic activity Mol. Pharmacol. 2009, 75, 1127-1136
24. Ward, D. I.; Jeffs, S. M.; Coe, P. L.; Walker, R. T. A Mild Procedure for the Anomerization of 2′-Deoxynucleosides Tetrahedron Lett. 1993, 34, 6779-6782
25. Sato, Y.; Tateno, G.; Seio, K.; Sekine, M. A convenient method for the conversion of beta-thymidine to alpha-thymidine based on TMSOTf-mediated C1′-epimerization Tetrahedron Lett. 2002, 43, 3251-3254 (Pubitemid 34310420)
26. Byun, Y.; Vogel, S. R.; Phipps, A. J.; Camrot, C.; Eriksson, S.; Tiwari, R.; Tjarks, W. Synthesis and biological evaluation of inhibitors of thymidine monophosphate kinase from Bacillus anthracis Nucleosides, Nucleotides Nucleic Acids 2008, 27, 244-260 (Pubitemid 351220652)
27. Smilkstein, M.; Sriwilaijaroen, N.; Kelly, J. X.; Wilairat, P.; Riscoe, M. Simple and inexpensive fluorescence-based technique for high-throughput antimalarial drug screening Antimicrob. Agents Chemother. 2004, 48, 1803-1806 (Pubitemid 38544392)
28. Knaggs, S.; Malkin, H.; Osborn, H. M. I.; Williams, N. A. O.; Yaqoob, P. New prodrugs derived from 6-aminodopamine and 4-aminophenol as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT) Org. Biomol. Chem. 2005, 3, 4002-4010 (Pubitemid 41640816)
29. Ruda, G. F.; Wong, P. E.; Alibu, V. P.; Norval, S.; Read, K. D.; Barrett, M. P.; Gilbert, I. H. Aryl phosphoramidates of 5-phospho erythronohydroxamic acid, a new class of potent trypanocidal compounds J. Med. Chem. 2010, 53, 6071-6078