Structure, absolute configuration, and conformation of the antimalarial drug artesunate View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2002-02

AUTHORS

J.N. Lisgarten, B. Potter, R.A. Palmer, B. Chimanuka, J. Aymami

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, Dc = 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. More... »

PAGES

43-48

References to SciGraph publications

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URI

http://scigraph.springernature.com/pub.10.1023/a:1015696306812

DOI

http://dx.doi.org/10.1023/a:1015696306812

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https://app.dimensions.ai/details/publication/pub.1030863414


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