Synthesis of new 6-alkylvinyl/arylalkylvinyl substituted 1,2,4-trioxanes active against multidrug-resistant malaria in mice

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 21, 2004, Pages 5553-5562

  Singh, Chandan ^a   Gupta, Nitin ^a   Puri, Sunil K ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

1,2,4 Trioxane; Antimalarial; Artemisinin; Photooxygenation; Plasmodium yoelii

Indexed keywords

1 (4 CHLOROPHENYL) 4 (1,2,5 TRIOXASPIRO[5.5]UNDEC 3 YL)PENT 4 EN 1 OL; 1 (4 CHLOROPHENYL) 4 (6,7,10 TRIOXASPIRO[4.5]DEC 8 YL)PENT 4 EN 1 OL; 1 BIPHENYL 4 YL 4 (1,2,5 TRIOXASPIRO[5.5]UNDEC 3 YL)PENTEN 1 OL; 1 BIPHENYL 4 YL 4 (6,7,10 TRIOXASPIRO[4.5]DEC 8 YL)PENT 4 EN 1 OL; 1 NAPHTHALEN 1 YL 4 (1,2,5 TRIOXASPIRO[5.5]UNDEC 3 YL)PENT 4 EN 1 OL; 1 NAPHTHALEN 1 YL 4 (6,7,10 TRIOXASPIRO[4.5]DEC 8 YL)PENT 4 EN 1 OL; 1 PHENYL 4 (1,2,5 TRIOXASPIRO[5.5]UNDEC 3 YL)PENT 4 EN 1 OL; 1 PHENYL 4 (1,2,5 TRIOXASPIRO[5.5]UNDEC 3 YL)PENT 4 EN 1 ONE; 1 PHENYL 4 (6,7,10 TRIOXASPIRO[4.5]DEC 8 YL)PENT 4 EN 1 OL; 3 (1 UNDECYLVINYL) 1,2,5 TRIOXASPIRO[5.5]UNDECANE; 5 (1,2,5 TRIOXASPIRO[5.5]UNDEC 3 YL)HEX 5 EN OL; 5 (6,7,10 TRIOXASPIRO[4.5]DEC 8 YL)HEX 5 EN 1 OL; 5 HEXYL 2 METHYL 2 VINYL TETRAHYDROFURAN; 8 (1 UNDECYLVINYL) 6,7,10 TRIOXASPIRO[5.5]UNDECANE; ANTIMALARIAL AGENT; SUCCINIC ACID [5 (1,2,5 TRIOXASPIRO[5.5]UNDEC 3 YL)HEX 5 ENYL]ESTER; SUCCINIC ACID [5 (6,7,10 TRIOXASPIRO[4.5]DEC 8 YL)HEX 5 ENYL]ESTER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG SYNTHESIS; MALARIA; MOUSE; MULTIDRUG RESISTANCE; NONHUMAN; PHOTOOXIDATION; PLASMODIUM YOELII; POLYMERIZATION;

ANIMALS; ANTIMALARIALS; DRUG RESISTANCE, MULTIPLE; MALARIA; MICE; PLASMODIUM YOELII; SESQUITERPENES;

PLASMODIUM YOELII;

EID: 4744374690     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.08.005     Document Type: Article

References (28)

1. D.L. Klayman Science 228 1985 1049
2. A.K. Bhattacharya, and R.P. Sharma Heterocycles 51 1999 1681
3. K. Borstnik, I. Paik, T.A. Shapiro, and G.H. Posner Int. J. Parasitol. 32 2002 1661
4. P. Ploypradith Acta Trop. 89 2004 329
5. P.M. O'Neill, and G.H. Posner J. Med. Chem. 47 2004 2945
6. P.M. O'Neill, M. Pugh, J. Davies, S.A. Ward, and B.K. Park Tetrahedron Lett. 42 2001 4569
7. A.J. Bloodworth, and K.A. Johnson Tetrahedron Lett. 35 1994 8057
8. A.J. Bloodworth, and A. Shah J. Chem. Soc., Chem. Commun. 1991 947
9. G.H. Posner, C.H. Oh, and W.K. Milhous Tetrahedron Lett. 32 1991 4235
10. W.H. Bunnelle, T.A. Isbell, C.L. Barnes, and S. Qualls J. Am. Chem. Soc. 113 1991 8168
11. M.A. Avery, C. Jennings-White, and W.K.M. Chong J. Org. Chem. 54 1989 1792
12. C. Singh Tetrahedron Lett. 31 1990 6901
13. J.A. Kepler, A. Philip, Y.W. Lee, M.C. Morey, and F.I. Caroll J. Med. Chem. 31 1988 713
14. C.W. Jefford, D. Jaggi, J. Boukouvalas, and S. Kohmoto J. Am. Chem. Soc. 105 1983 6498
15. W. Peters, B.L. Robinson, J.C. Rossier, and C.W. Jefford Ann. Trop. Med. Parasitol. 87 1993 1
16. G.H. Posner, H.B. Jeon, M.H. Parker, M. Krasavin, I.-H. Paik, and T.A. Shapiro J. Med. Chem. 44 2001 3054
17. G.H. Posner, H.B. Jeon, P. Polypradith, I.-H. Paik, K. Borstnik, S. Xie, and T.A. Shapiro J. Med. Chem. 45 2002 3824
18. C. Singh, D. Misra, G. Saxena, and S. Chandra Bioorg. Med. Chem. Lett. 2 1992 497
19. C. Singh, D. Misra, G. Saxena, and S. Chandra Bioorg. Med. Chem. Lett. 5 1995 1913
20. For preliminary results of this study see: C. Singh, N. Gupta, and S.K. Puri Bioorg. Med. Chem. Lett. 13 2003 3447
21. D.S. Dodd, A.C. Oehlschlager;, N.H. Georgopapadakou, A.-M. Polok, and P.G. Hartman J. Org. Chem. 57 1992 7226
22. Acid catalyzed cyclization of 2-hexene-1,6-diols to 2-vinyl tetrahydrofurans is well documented see, for example: G. Ohloff, K.-H. Schulte-Elte, and B. Willhalm Helv. Chim. Acta 47 1964 602
23. R.W. Ratcliffe Org. Synth. 55 1976 84 86
24. S.K. Puri, and N. Singh Expl. Parasitol. 94 2000 8
25. R.A. Bunce, and C.R. Harris J. Org. Chem. 57 1992 6981
26. V. Jarolim, and F. Sorm Collect. Czech. Chem. Commun. 41 1976 1066
27. For an alternative preparation from aldehyde acetate 22 see: T. Nakata, S. Nomura, and H. Matsukara Tetrahedron Lett. 37 1996 213
28. H. Gilman, N.B. St. John, and F. Schulze Org. Synth. Coll. 2 1943 425