Abstract
The crystal and molecular structure of the antimalarial compound artesunate has been determined by direct methods. Crystals are orthorhombic, P212121, a = 9.8371(12), b = 10.517(2), c = 18.7594(5) Å, Z = 4, D c = 1.316 mg/mL. The molecule is comprised of a fused ring system containing a six-membered ring C which includes an oxygen bridge and a peroxy bridge. The 9-atom oxygen–carbon chain from O(5)—C(12)... to ... O(2)—C(6) displays a striking sequence of short, long, short, long ... bonds while these distances are all within the ranges of a normal single bond or partial double bond. It is proposed that this pattern is caused by the delocalization of the lone pair electrons on the oxygen atoms. The ring C has a distorted boat conformation and the C—O—O—C torsion angle is 46.3(2)°. Rings A and D have ideal chair conformations. Ring junctions A/B and A/D are cis junctions, B/D and C/D are trans. Packing of the molecules is stabilized by one strong hydrogen bond involving the hydroxyl group on the ester linkage and the oxygen atom of the lactone ring.
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Luo, X.D.; Shen, C.C. Med. Res. Rev. 1987, 7, 29–52.
China Cooperative Research Group. J. Tradit Chin. Med. 1982, 2, 45.
Abadi, Y.; Gustafsson, L.; Ericsonn, O.; Hellgren, U. Handbook of Drugs for Tropical Parasitic Infections, 2nd ed.; Taylor and Francis: London, 1995; p 27.
Klayman, D.L. Science 1985, 228, 1049–1055.
Zhang, F.; Gosser, D.K.; Meshnick, S.R. Biochem. Pharmacol. 1992, 43, 1805–1809.
Meshnich, S.R.; Yang, Y.Z.; Lima, V.; Kuypers, F.; Kamchonwongpaisan, S.; Yuthavong, Y. Antimicrob. Agents Chemother. 1993, 37, 1108–1114.
Farrugia, L.J. J. Appl. Crystallogr. 1999, 32, 837–838.
Flack, H.D. Acta Crystallogr. A 1983, 39, 876–881.
Duax, W.L., Norton, D.A. Atlas of Steroid Structure; Plenum: New York, 1975.
Lisgarten, J.N.; Potter, B.; Palmer, R.A.; Chimanuka, B. J. Chem. Crystallogr. 1998, 28(7), 539–543.
Luo, X.D.; Yeh, H.J.C.; Brossi, A.; Flippen-Anderson, J.; Gilardi, R. Helvitica Chim. Acta 1984, 67, 1515–1522.
Lisgarten, J.N.; Potter B.; Palmer, R.A.; Chimanuka, B. J. Chem. Crystallogr., submitted.
Allen, F.H.; Kennard, O.; Watson, D.G.; Brammer, L.; Orpen, A.G.; Taylor, R. J. Chem. Soc. Perkin Trans. 1987, 2, S1.
Enraf-Nonius CAD-4 Software; Enraf-Nonius: Delft, Holland, 1988.
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Lisgarten, J., Potter, B., Palmer, R. et al. Structure, absolute configuration, and conformation of the antimalarial drug artesunate. Journal of Chemical Crystallography 32, 43–48 (2002). https://doi.org/10.1023/A:1015696306812
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DOI: https://doi.org/10.1023/A:1015696306812