A carbonyl oxide route to antimalarial Yingzhaosu A analogues: Synthesis and antimalarial activity

Tetrahedron Letters

Volumn 39, Issue 33, 1998, Pages 6065-6068

  O'Neill, Paul M ^a   Searle, Natalie L ^a   Raynes, Kaylene J ^a   Maggs, James L ^a   Ward, Stephen A ^a   Storr, Richard C ^a   Park, B Kevin ^a   Posner, Gary H ^b  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; ARTEFLENE; ARTEMISIN; OZONE; UNCLASSIFIED DRUG; YINGZHAOSU A DERIVATIVE;

ANTIMALARIAL ACTIVITY; ARTICLE; CYCLIZATION; DRUG POTENCY; DRUG RESISTANCE; DRUG SYNTHESIS; MEDICINAL PLANT; NONHUMAN; PLASMODIUM FALCIPARUM; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

PLASMODIUM FALCIPARUM;

EID: 0032514426     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01248-9     Document Type: Article

References (11)

1. 1. Jefford, C.W.; Kohmoto, S.; Jaggi, D.; Timari, J.; 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.
2. 2. Hofheinz, W.; Burgin, H.; Gocke, E.; Jaquet, R.; Masciadri, R.; Schmid, S.; Stohler, H.; Urwyler, H. Trop. Med. Parasitol., 1994, 45, 261.
3. 3. Meshnick, S.R.; Jefford, C.W.; Posner, G.H.; Avery, M.A.; Peters, W., Parasitol. Today, 1996, 12, 79.
4. 4. Dussault, P.H.; Zope, U.R. J. Org. Chem., 1995, 60, 8218.
5. 5. Ushigoe, Y.; Masuyama, A.; Nojima, M.; Mc Cullough, K.J., Tetrahedron Lett., 1997, 38, 8753.
6. 4, 100), 299 (36), 169 (25).
7. 1H NMR of the intermediate hydroperoxy ketals revealed two methoxyl signals at 3.34 ppm and 3.32 ppm
8. 8. Schreiber, S.L.; Liew, W.F., Tetrahedron Lett., 1983, 24, 2363.
9. 9. Desjardins, R.E.; Canfield, J ; Haynes, D.; Chulay, D.J., Antimicrob. Agents Chemother., 1979, 16, 710.
10. 10. For the first report of a carbon-centered radical intermediate in iron (H) promoted reductive cleavage of an antimalarial trioxane see: Posner, G.H.; Cumming, J.N.; Ploypradith, P.; Oh. C.H. J. Am. Chem. Soc, 1995, 117, 5885.
11. 3. Data were collected with a Siemens R3m/V diffractometer. Wavelength 0.71073 A, Temperature, 153K. Crystal system, space group = monoclinic, P2 (1). Cystal size 0.35 × 0.10 × 0.08 mm, a = 6.429(3) b = 9.469(4) c = 8.526 (4). A total of 1373 reflections were collected in the 5°<2<45° range using 0.093 ω /2θ scans. 1247 reflections were unique. Lorentz and polarization but not absorbtion co-efficients were applied. The structure was solved by direct methods (SHEXS-86). The refinement was converged to R1 = 5.82% wR2 = 20.91 and a final difference map grater than 0.51 e/A. Complete details of the structure are available at request from the Cambridge Crystal Data Centre, 12 Union Road, Cambridge CB2 1EZ, England