1,2,4,5-tetraoxacycloalkanes: Synthesis and antimalarial activity

Mini-Reviews in Medicinal Chemistry

Volumn 5, Issue 11, 2005, Pages 1035-1043

  Masuyama, A ^a   Wu, J M ^a   Nojima, M ^a   Kim, H S ^b   Wataya, Y ^b  

^a OSAKA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

1,2,4,5 tetraoxacycloalkanes; 1,2,5,6 tetraoxacycloalkanes; 1,2,6,7 tetraoxaspiro 7.11 nonadecane; Antimalarial activity; Cyclization methods; Medium sized cyclic peroxides; P. berghei; P. falciparum

Indexed keywords

(ALKENYLDIOXY)CYCLODODECYL HYDROPEROXIDE DERIVATIVE; 1,1 BIS(METHYLDIOXY)CYCLODODECANE; 1,2 BISHYDROPEROXIDE; 1,2,4 TROXEPANE DERIVATIVE; 1,2,4,5 TETRAOXACYCLOALKANE DERIVATIVE; 1,2,4,5 TETROXOCANE DERIVATIVE; 2 PHENYLNORBORNENE; ANTIMALARIAL AGENT; ARTEMISININ; HYDROPEROXIDE; IODINE DERIVATIVE; N,O BIS(TRIMETHYLSILYL)ACETAMINDE DERIVATIVE; PERACETAL; PEROXYLACTONE DERIVATIVE; PRODRUG; SPIRO 1,2,4,5 TETROXOCANE DERIVATIVE; SPIROTETRAOXACYCLOALKANE DERIVATIVE; TETROXEPANE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; CHEMICAL PROCEDURES; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; MALARIA; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; REVIEW;

ANIMALS; ANTIMALARIALS; CYCLOPARAFFINS; DRUG DESIGN; HUMANS;

EID: 26944458138     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/138955705774575255     Document Type: Review

References (38)

1. (a) Borstnik, K.; Paik, I.-H.; Shapiro, T. A.; Posner, G. H. Int. J. Parasitol. 2002, 32, 1661-1667;
2. (b) McCullough, K. J.; Nojima, M. Current Org. Chem. 2001, 5, 601-636;
3. (c) Posner, G. H.; O'Neill, P. M. Acc. Chem. Res. 2004, 37, 397-404;
4. (d) Haynes, R. K.; Ho, W.-Y.; Chan, H.-W.; Fugmann, B.; Stetter, J.; Croft, S. L.; Vivas, L.; Peters. W.; Robinson, B. L. Angew. Chem. Int. Ed. 2004, 43, 1381-1385.
5. Dong, Y. Mini Rev. Med. Chem. 2002, 2, 113-123.
6. (a) Dong, Y. Mini Rev. Med Chem. in press;
7. (b) Jefford, C. W.; Li, Y.; Jaber, A.; Boukouvalas, J. Synth. Commun. 1990, 20, 2589-2596;
8. (c) Kim, H.-S.; Tsuchiya, K.; Shibata, Y.; Wataya, Y.; Ushigoe, Y.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Chem. Soc., Perkin Trans. 1 1999, 1867-1870;
9. (d) Terent'ev, A. O.; Kutkin, A. V.; Platonov, M. M.; Ogibin, Y. N.; Nikishin, G. I. Tetrahedron Lett. 2003, 44, 7359-7363;
10. (e) Iskra, J.; Bonnet-Delpon, D.; Begue, J.-P. Tetrahedron Lett. 2003, 44, 6309-6312;
11. (f) Solaja, B.; A. Terzic, N.; Pocsfalvi, G.; Gerena, L.; Tinant, B.; Opsenica, D.; Milhous, W. K. J. Med. Chem. 2002, 45, 3331-3336.
12. (a) Dussault, P. H. Sahli, A. J. Org. Chem. 1992, 57, 1009-1012;
13. (b) Dussault, P. H.; Zope, U. R. J. Org. Chem. 1995, 60, 8218-8222.
14. (a) Bloodworth, A. J.; Eggelte, H. J. J. Chem. Soc., Perkin Trans. 1 1981, 3272-3278;
15. (b) Adam, W.; Birke, A.; Cadiz, C.: Diaz, S.; Rodoriguez, A. J. Org. Chem. 1978, 43, 1154-1158.
16. (a) Tsuchiya, K.; Hamada, Y.; Masuyama, A.; Nojima, M.; McCullough, K. J.; Kim, H.-S.; Shibata, Y.; Wataya, Y. Tetrahedron Lett. 1999, 40, 4077-4080;
17. (b) Kim, H.-S.; Nagai, Y.; Ono, K.; Begum, K.; Wataya, Y.; Hamada, Y.; Tsuchiya, K.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Med. Chem. 2001, 44, 2357-2361.
18. Hamada, Y.; Tokuhara, H.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Ono, K.; Ogura, N.; Wataya, Y. J. Med. Chem. 2002, 45, 1374-1378.
19. Adam, W.; Bruenker, H.-G.; Kumar, A. S.; Peters, K.; Schneider, U.; Von Schnering, H.G. J. Am. Chem. Soc. 1996, 118, 1899-1905.
20. Jefford, C. W. Chem. Soc. Rev. 1993, 59-66.
21. (a) McCullough, K. J.; Nonami, Y.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Wataya, Y. Tetrahedron Lett. 1999, 40, 9151-9155;
22. (b) Kim, H.-S.; Begum, K.; Ogura, N.; Wataya, Y.; Nonami, Y.; Ito, T.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Med. Chem. 2003, 46, 1957-1961.
23. (a) Bloodworth, A. J.; Shah. A. Tetrahedron Lett. 1993, 34, 6643-6646;
24. (b) Bloodworth, A. J.; Bothwell, B. D.; Collins, A. N.; Maidwell, N. L. Tetrahedron Lett. 1996, 37, 1885-1888.
25. (a) Dussault, P. H.; Davies, D. R. Tetrahedron Lett., 1996, 37, 463-466;
26. (b) Ushigoe, Y.: Kano, Y.; Nojima, M. J. Chem. Soc., Perkin Trans. 1 1997, 5-10;
27. (c) Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Org. Chem. 2000, 65, 1069-1075.
28. Rousseau, G.; Homsi, F. Chem. Soc. Rev. 1997, 26, 453-461.
29. Nonami, Y.; Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J.; Kim, H.-S.; Wataya, Y. Tetrahedron Lett. 1999, 40, 4681-4684.
30. (a) McCullough, K. J.; Ito, T.; Tokuyasu, T.; Masuyama, A.; Nojima, M. Tetrahedron Lett. 2001, 42, 5529-5532;
31. (b) Ito, T.; Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J. Tetrahedron 2003, 59, 525-536.
32. (a) Ushigoe, Y.: Torao, Y.; Masuyama, A.; Nojima. M. J. Org. Chem. 1997, 62, 4949-4954;
33. (b) Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J.; Kim, H.-S.; Wataya, Y. Tetrahedron 2001, 57, 5979-5989.
34. McCullough, K. J.; Tokuhara, H.; Masuyama, A.; Nojima, M. Org. Biomol. Chem. 2003, 1, 1522-1527.
35. (a) Oh, C. H.; Kang, J. H. Tetrahedron Lett. 1998, 39, 2771-2774;
36. (b) Dussault, P. H.; Trullinger, T. K.; Noor-e-Ain, F. Org. Lett. 2002, 4, 4591-4593.
37. (a) Oh, C. H.; Kim, H. J.; Wu, S. H.; Won, H. S. Tetrahedron Lett. 1999, 40, 8391-8394;
38. (b) O'Neill, P. M.; Hindley, S.; Pugh, M. D.; Davies, J.; Bray, P. G.; Park, B. K.; Kapu, D. S.; Ward, S. A.; Stocks, P. A. Tetrahedron Lett. 2003, 44, 8135-8139.