Mechanism-based design of simple, symmetrical, easily prepared, potent antimalarial endoperoxides

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 815-818

  Posner, Gary H ^a   Wang, Dasong ^a   González, Lluïsa ^a   Tao, Xueliang ^a   Cumming, Jared N ^a   Klinedinst, Donna ^b   Shapiro, Theresa A ^b  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; ARTEMISININ; BICYCLO[3.2.2]NONANE DERIVATIVE; CHLOROQUINE; ENDOPEROXIDE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION;

EID: 0030026909     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02329-1     Document Type: Article

References (30)

1. For reviews, see: (a) Klayman, D.L. Science 1985, 228, 1049; (b) White, N.J. Trans. R. Soc. Trop. Med. Hyg. 1994, 88 (Suppl. 1), 1; (c) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211; (d) Jung, M. Curr. Med. Chem. 1994, 1, 45; (e) McCullough, K.J. Contemp. Org. Syn. 1995, 2, 225; (f) see also, Avery, M.A.; Gao, F.; Chong, W.K.M.; Hendrickson, T.F.; Inman, W.D.; Crews, P. Tetrahedron 1994, 50, 9547.
2. For reviews, see: (a) Klayman, D.L. Science 1985, 228, 1049; (b) White, N.J. Trans. R. Soc. Trop. Med. Hyg. 1994, 88 (Suppl. 1), 1; (c) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211; (d) Jung, M. Curr. Med. Chem. 1994, 1, 45; (e) McCullough, K.J. Contemp. Org. Syn. 1995, 2, 225; (f) see also, Avery, M.A.; Gao, F.; Chong, W.K.M.; Hendrickson, T.F.; Inman, W.D.; Crews, P. Tetrahedron 1994, 50, 9547.
3. For reviews, see: (a) Klayman, D.L. Science 1985, 228, 1049; (b) White, N.J. Trans. R. Soc. Trop. Med. Hyg. 1994, 88 (Suppl. 1), 1; (c) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211; (d) Jung, M. Curr. Med. Chem. 1994, 1, 45; (e) McCullough, K.J. Contemp. Org. Syn. 1995, 2, 225; (f) see also, Avery, M.A.; Gao, F.; Chong, W.K.M.; Hendrickson, T.F.; Inman, W.D.; Crews, P. Tetrahedron 1994, 50, 9547.
4. For reviews, see: (a) Klayman, D.L. Science 1985, 228, 1049; (b) White, N.J. Trans. R. Soc. Trop. Med. Hyg. 1994, 88 (Suppl. 1), 1; (c) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211; (d) Jung, M. Curr. Med. Chem. 1994, 1, 45; (e) McCullough, K.J. Contemp. Org. Syn. 1995, 2, 225; (f) see also, Avery, M.A.; Gao, F.; Chong, W.K.M.; Hendrickson, T.F.; Inman, W.D.; Crews, P. Tetrahedron 1994, 50, 9547.
5. For reviews, see: (a) Klayman, D.L. Science 1985, 228, 1049; (b) White, N.J. Trans. R. Soc. Trop. Med. Hyg. 1994, 88 (Suppl. 1), 1; (c) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211; (d) Jung, M. Curr. Med. Chem. 1994, 1, 45; (e) McCullough, K.J. Contemp. Org. Syn. 1995, 2, 225; (f) see also, Avery, M.A.; Gao, F.; Chong, W.K.M.; Hendrickson, T.F.; Inman, W.D.; Crews, P. Tetrahedron 1994, 50, 9547.
6. For reviews, see: (a) Klayman, D.L. Science 1985, 228, 1049; (b) White, N.J. Trans. R. Soc. Trop. Med. Hyg. 1994, 88 (Suppl. 1), 1; (c) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211; (d) Jung, M. Curr. Med. Chem. 1994, 1, 45; (e) McCullough, K.J. Contemp. Org. Syn. 1995, 2, 225; (f) see also, Avery, M.A.; Gao, F.; Chong, W.K.M.; Hendrickson, T.F.; Inman, W.D.; Crews, P. Tetrahedron 1994, 50, 9547.
7. For recent references, see: (a) Boukouvalas, J.; Pouliot, R.; Fréchette, Y. Tetrahedron Lett. 1995, 36, 4167; (b) Jiang, H.-L.; Chen, K.-X.; Tang, Y.; Chen, J.-Z.; Ji, R.-Y. Chinese J. Chem. 1995, 13, 131; (c) Singh, C.; Misra, D.; Saxena, G.; Chandra, S. Bioorg. Med. Chem. Lett. 1995, 17, 1913; (d) Venugopalan, B.; Bapat, C.P.; Karnik, P.J.; Chatterjee, D.K.; Iyer, N.; Lepcha, D. J. Med. Chem. 1995, 38, 1922; (e) Jefford, C.W.; Kohmoto, S.; Jaggi, D.; Timari, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gerard, D.; Burger, U.; Kamalaprija, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C.J.; Fleck, S.L.; Robinson, B.L.; Peters, W. Helv. Chim. Acta 1995, 78, 647; (f) Posner, G.H.; McGarvey, D.M.; Oh, C.H.; Kumar, N.; Meshnick, S.R.; Asawamahasadka, W. J. Med. Chem. 1995, 38, 607; (g) Posner, G.H.; Oh, C.H.; Gerena, L.; Milhous, W.K. Heteroatom Chem. 1995, 6, 105.
8. For recent references, see: (a) Boukouvalas, J.; Pouliot, R.; Fréchette, Y. Tetrahedron Lett. 1995, 36, 4167; (b) Jiang, H.-L.; Chen, K.-X.; Tang, Y.; Chen, J.-Z.; Ji, R.-Y. Chinese J. Chem. 1995, 13, 131; (c) Singh, C.; Misra, D.; Saxena, G.; Chandra, S. Bioorg. Med. Chem. Lett. 1995, 17, 1913; (d) Venugopalan, B.; Bapat, C.P.; Karnik, P.J.; Chatterjee, D.K.; Iyer, N.; Lepcha, D. J. Med. Chem. 1995, 38, 1922; (e) Jefford, C.W.; Kohmoto, S.; Jaggi, D.; Timari, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gerard, D.; Burger, U.; Kamalaprija, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C.J.; Fleck, S.L.; Robinson, B.L.; Peters, W. Helv. Chim. Acta 1995, 78, 647; (f) Posner, G.H.; McGarvey, D.M.; Oh, C.H.; Kumar, N.; Meshnick, S.R.; Asawamahasadka, W. J. Med. Chem. 1995, 38, 607; (g) Posner, G.H.; Oh, C.H.; Gerena, L.; Milhous, W.K. Heteroatom Chem. 1995, 6, 105.
9. For recent references, see: (a) Boukouvalas, J.; Pouliot, R.; Fréchette, Y. Tetrahedron Lett. 1995, 36, 4167; (b) Jiang, H.-L.; Chen, K.-X.; Tang, Y.; Chen, J.-Z.; Ji, R.-Y. Chinese J. Chem. 1995, 13, 131; (c) Singh, C.; Misra, D.; Saxena, G.; Chandra, S. Bioorg. Med. Chem. Lett. 1995, 17, 1913; (d) Venugopalan, B.; Bapat, C.P.; Karnik, P.J.; Chatterjee, D.K.; Iyer, N.; Lepcha, D. J. Med. Chem. 1995, 38, 1922; (e) Jefford, C.W.; Kohmoto, S.; Jaggi, D.; Timari, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gerard, D.; Burger, U.; Kamalaprija, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C.J.; Fleck, S.L.; Robinson, B.L.; Peters, W. Helv. Chim. Acta 1995, 78, 647; (f) Posner, G.H.; McGarvey, D.M.; Oh, C.H.; Kumar, N.; Meshnick, S.R.; Asawamahasadka, W. J. Med. Chem. 1995, 38, 607; (g) Posner, G.H.; Oh, C.H.; Gerena, L.; Milhous, W.K. Heteroatom Chem. 1995, 6, 105.
10. For recent references, see: (a) Boukouvalas, J.; Pouliot, R.; Fréchette, Y. Tetrahedron Lett. 1995, 36, 4167; (b) Jiang, H.-L.; Chen, K.-X.; Tang, Y.; Chen, J.-Z.; Ji, R.-Y. Chinese J. Chem. 1995, 13, 131; (c) Singh, C.; Misra, D.; Saxena, G.; Chandra, S. Bioorg. Med. Chem. Lett. 1995, 17, 1913; (d) Venugopalan, B.; Bapat, C.P.; Karnik, P.J.; Chatterjee, D.K.; Iyer, N.; Lepcha, D. J. Med. Chem. 1995, 38, 1922; (e) Jefford, C.W.; Kohmoto, S.; Jaggi, D.; Timari, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gerard, D.; Burger, U.; Kamalaprija, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C.J.; Fleck, S.L.; Robinson, B.L.; Peters, W. Helv. Chim. Acta 1995, 78, 647; (f) Posner, G.H.; McGarvey, D.M.; Oh, C.H.; Kumar, N.; Meshnick, S.R.; Asawamahasadka, W. J. Med. Chem. 1995, 38, 607; (g) Posner, G.H.; Oh, C.H.; Gerena, L.; Milhous, W.K. Heteroatom Chem. 1995, 6, 105.
11. For recent references, see: (a) Boukouvalas, J.; Pouliot, R.; Fréchette, Y. Tetrahedron Lett. 1995, 36, 4167; (b) Jiang, H.-L.; Chen, K.-X.; Tang, Y.; Chen, J.-Z.; Ji, R.-Y. Chinese J. Chem. 1995, 13, 131; (c) Singh, C.; Misra, D.; Saxena, G.; Chandra, S. Bioorg. Med. Chem. Lett. 1995, 17, 1913; (d) Venugopalan, B.; Bapat, C.P.; Karnik, P.J.; Chatterjee, D.K.; Iyer, N.; Lepcha, D. J. Med. Chem. 1995, 38, 1922; (e) Jefford, C.W.; Kohmoto, S.; Jaggi, D.; Timari, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gerard, D.; Burger, U.; Kamalaprija, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C.J.; Fleck, S.L.; Robinson, B.L.; Peters, W. Helv. Chim. Acta 1995, 78, 647; (f) Posner, G.H.; McGarvey, D.M.; Oh, C.H.; Kumar, N.; Meshnick, S.R.; Asawamahasadka, W. J. Med. Chem. 1995, 38, 607; (g) Posner, G.H.; Oh, C.H.; Gerena, L.; Milhous, W.K. Heteroatom Chem. 1995, 6, 105.
12. For recent references, see: (a) Boukouvalas, J.; Pouliot, R.; Fréchette, Y. Tetrahedron Lett. 1995, 36, 4167; (b) Jiang, H.-L.; Chen, K.-X.; Tang, Y.; Chen, J.-Z.; Ji, R.-Y. Chinese J. Chem. 1995, 13, 131; (c) Singh, C.; Misra, D.; Saxena, G.; Chandra, S. Bioorg. Med. Chem. Lett. 1995, 17, 1913; (d) Venugopalan, B.; Bapat, C.P.; Karnik, P.J.; Chatterjee, D.K.; Iyer, N.; Lepcha, D. J. Med. Chem. 1995, 38, 1922; (e) Jefford, C.W.; Kohmoto, S.; Jaggi, D.; Timari, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gerard, D.; Burger, U.; Kamalaprija, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C.J.; Fleck, S.L.; Robinson, B.L.; Peters, W. Helv. Chim. Acta 1995, 78, 647; (f) Posner, G.H.; McGarvey, D.M.; Oh, C.H.; Kumar, N.; Meshnick, S.R.; Asawamahasadka, W. J. Med. Chem. 1995, 38, 607; (g) Posner, G.H.; Oh, C.H.; Gerena, L.; Milhous, W.K. Heteroatom Chem. 1995, 6, 105.
13. For recent references, see: (a) Boukouvalas, J.; Pouliot, R.; Fréchette, Y. Tetrahedron Lett. 1995, 36, 4167; (b) Jiang, H.-L.; Chen, K.-X.; Tang, Y.; Chen, J.-Z.; Ji, R.-Y. Chinese J. Chem. 1995, 13, 131; (c) Singh, C.; Misra, D.; Saxena, G.; Chandra, S. Bioorg. Med. Chem. Lett. 1995, 17, 1913; (d) Venugopalan, B.; Bapat, C.P.; Karnik, P.J.; Chatterjee, D.K.; Iyer, N.; Lepcha, D. J. Med. Chem. 1995, 38, 1922; (e) Jefford, C.W.; Kohmoto, S.; Jaggi, D.; Timari, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gerard, D.; Burger, U.; Kamalaprija, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C.J.; Fleck, S.L.; Robinson, B.L.; Peters, W. Helv. Chim. Acta 1995, 78, 647; (f) Posner, G.H.; McGarvey, D.M.; Oh, C.H.; Kumar, N.; Meshnick, S.R.; Asawamahasadka, W. J. Med. Chem. 1995, 38, 607; (g) Posner, G.H.; Oh, C.H.; Gerena, L.; Milhous, W.K. Heteroatom Chem. 1995, 6, 105.
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