Anti-malarial activity of N6-modified purine analogues

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 16, 2007, Pages 5551-5562

  Too, Kathleen ^a   Brown, Daniel M ^a   Bongard, Emily ^b   Yardley, Vanessa ^b   Vivas, Livia ^b   Loakes, David ^a  

^a MRC LABORATORY OF MOLECULAR BIOLOGY   (United Kingdom)

^b LONDON SCHOOL OF HYGIENE AND TROPICAL MEDICINE   (United Kingdom)

Author keywords

Malaria; Nucleosides; Plasmodium; Purine analogues; Tautomerism

Indexed keywords

2 AMINO 6 N HYDROXYADENINE; 2 AMINO 6 N METHOXYADENINE; 2 AMINO N 6 AMINO N 6 METHYLADENINE; 2 AMINO N 6 AMINO N 6 METHYLADENOSINE; 2 AMINO N 6 AMINOADENINE; 2 AMINO N 6 AMINOADENOSINE; 2 AMINO N 6 BENZYLOXYADENOSINE; 2 AMINO N 6 METHOXY N 6 METHYLADENOSINE; 2 AMINO N 6 METHOXYADENOSINE; 6 (2 ETHYLIDENE 1 PHENYLHYDRAZINYL) 9H PURINE; 6 N METHOXYADENOSINE; CHLOROQUINE; N 6 ALLYLOXYADENOSINE; N 6 AMINO N 6 METHYLADENINE; N 6 AMINO N 6 METHYLADENOSINE; N 6 AMINO N 6 PHENYLADENINE; N 6 AMINOADENINE; N 6 AMINOADENOSINE; N 6 BENZYLOXYADENINE; N 6 BENZYLOXYADENOSINE; N 6 HYDROXYADENINE; N 6 METHOXY N 6 METHYLADENINE; N 6 METHOXY N 6 METHYLADENOSINE; N 6 METHOXYADENINE; N 6 PHENYLAMINOADENINE; N 6 PHENYLAMINOADENOSINE; PODOPHYLLOTOXIN; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; MALARIA; MALE; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM;

ANIMALS; ANTIMALARIALS; MALE; MICE; MOLECULAR STRUCTURE; PLASMODIUM FALCIPARUM; PURINES; STRUCTURE-ACTIVITY RELATIONSHIP;

PLASMODIUM FALCIPARUM;

EID: 34250723436     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.05.038     Document Type: Article

References (43)

1. Fidock D.A., Rosenthal P.J., Croft S.L., Brun R., and Nwaka S. Nat. Rev. Drug Discov. 3 (2004) 509-520
2. Lawton P. Expert Opin. Ther. Patents 15 (2005) 987-994
3. Klinkert M.-Q., and Heussler V. Mini-Rev. Med. Chem. 6 (2006) 131-143
4. Carter N.S., Ben Mamoun C., Liu W., Silva E.O., Landfear S.M., Goldberg D.E., and Ullman B. J. Biol. Chem. 275 (2000) 10683-10691
5. Parker M.D., Hyde R.J., Yao S.Y., McRobert L., Cass C.E., Young J.D., McConkey G.A., and Baldwin S.A. Biochem. J. 349 (2000) 67-75
6. Downie M.J., Saliba K.J., Howitt S.M., Broer S., and Kirk K. Mol. Microbiol. 60 (2006) 738-748
7. El Bissati K., Zufferey R., Witola W.H., Carter N.S., Ullman B., and Ben Mamoun C. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 9286-9291
8. King A.E., Ackley M.A., Cass C.E., Young J.D., and Baldwin S.A. Trends Pharmacol. Sci. 27 (2006) 416-425
9. De Koning H.P., Bridges D.J., and Burchmore R.J.S. FEMS Microbiol. Rev. 29 (2005) 987-1020
10. El Kouni M.H. Pharmacol. Ther. 99 (2003) 283-309
11. Legraverend M., and Grierson D.S. Bioorg. Med. Chem. 14 (2006) 3987-4006
12. Shi W., Ting L.-M., Kicska G.A., Lewandowicz A., Tyler P.C.B.E.G., Furneaux R.H., Kim K., Almo S.C., and Schramm V.L. J. Biol. Chem. 279 (2004) 18103-18106
13. Berman J.D., Lee L.S., Robins R.K., and Revankar G.R. Antimicrob. Agents Chemother. 24 (1983) 233-236
14. Hasan A., Satyanarayana M., Mishra A., Bhakuni D.S., Pratap R., Dube A., and Guru P.Y. Nucleosides, Nucleotides & Nucleic Acids 25 (2006) 55-60
15. Drew M.E., Morris J.C., Wang Z., Wells L., Sanchez M., Landfear S.M., and Englund P.T. J. Biol. Chem. 278 (2003) 46596-46600
16. Gallerano R.H., Marr J.J., and Sosa J.J. Am. J. Trop. Med. Hyg. 43 (1990) 159-166
17. Croft S.L., Barrett M.P., and Urbina J.A. Trends Parasitol. 2 (2005) 508-512
18. Brown D.M., Hewlins M.J.E., and Schell P. J. Chem. Soc. (C) 15 (1968) 1925-1929
19. LaPointe S.M., Wheaton C.A., and Wetmore S.D. Chem. Phys. Lett. 2004 (2004) 487-493
20. Hill F., Williams D.M., Loakes D., and Brown D.M. Nucleic Acids Res. 26 (1998) 1144-1149
21. Loakes D., Brown D.M., Mahmood N., Balzarini J., and De Clerq E. Antiviral Chem. Chemother. 6 (1994) 9-16
22. Stolarski R., Kierdaszuk B., Hagberg C.-E., and Shugar D. Biochemistry 26 (1987) 4332-4337
23. Pierra C., Amador A., Benzaria S., Cretton-Scott E., D'Amours M., Mao J., Matthieu S., Moussa A., Bridges E.G., Stamdring D.N., Sommadossi J.-P., Storer R., and Gosselin G. J. Med. Chem. 49 (2006) 6614-6620
24. Moreno A., Badell E., Van Rooijen N., and Druilhe P. Antimicrob. Agents Chemother. 45 (2001) 1847-1853
25. Quashie, N. B.; Dorin, D.; Too, K.; Bray, P. G.; Brown, D. M.; Loakes, D.; Doerig, C.; Ranford-Cartwright, L. C.; de Koning, H. P., submitted for publication.
26. Rainey P., and Santi D.V. Proc. Natl. Acad. Sci. U.S.A. 80 (1983) 282-288
27. Gros L., Lorente S.O., Jimenez C.J., Yardley V., Rattray L., Wharton H., Little S., Croft S.L., Ruiz-Perez L.M., Gonzalez-Pacanowska D., and Gilbert I.H. J. Med. Chem. 49 (2006) 6094-6103
28. Giner-Sorolla A., O'Bryant S.A., Nanos C., Dollinger M.R., Bendich A., and Burchenal J.H. J. Med. Chem. 11 (1968) 521-523
29. Montero J.-L.G., Bhat G.A., Panzica R.P., and Townsend L.B. J. Het. Chem. 14 (1977) 483-487
30. Naito T., Ueno K., and Ishikawa F. Chem. Pharm. Bull. 12 (1964) 951-954
31. Giner-Sorolla A., and Bendich A. J. Am. Chem. Soc. 80 (1958) 3932-3937
32. Prasad R.N., and Robins R.K. J. Am. Chem. Soc. 79 (1957) 6401-6407
33. Johnson J.A.J., Thomas H.J., and Schaeffer H.J. J. Am. Chem. Soc. 80 (1958) 699-702
34. Montgomery J.A., and Holum L.B. J. Am. Chem. Soc. 79 (1957) 2185-2188
35. Montgomery J.A., and Temple C. J. Am. Chem. Soc. 83 (1961) 630-635
36. Fujii T., Wu C.C., Itaya T., Moro S., and Saito T. Chem. Pharm. Bull. 21 (1973) 1676-1682
37. Fujii T., Saito T., Itaya T., Kizu K., Kumazawa Y., and Nakajima S. Chem. Pharm. Bull. 35 (1987) 4482-4493
38. Miura K., Kasai T., and Ueda T. Chem. Pharm. Bull. 23 (1975) 464-466
39. Ueda T., Miura K., and Kasai T. Chem. Pharm. Bull. 26 (1978) 2122-2127
40. Fujii T., and Saito T. Chem. Pharm. Bull. 38 (1990) 1886-1891
41. Fujii T., Itaya T., Tanaka F., Saito T., Mohri K., and Yamamoto K. Chem. Pharm. Bull. 31 (1983) 3149-3159
42. Desjardins R.E., Canfield C.J., Haynes J.D., and Chulay J.D. Antimicrob. Agents Chemother. 16 (1979) 710-718
43. Vivas L., Easton A., Kendrick H., Cameron A., Lavandera J.L., Barros D., de las Heras F.G., Brady R.L., and Croft S.L. Exp. Parasitol. 111 (2005) 105-114