255730-18-8Relevant articles and documents
Absorption of the novel artemisinin derivatives artemisone and artemiside: Potential application of Pheroid technology
Steyn, J. Dewald,Wiesner, Lubbe,Du Plessis, Lissinda H.,Grobler, Anne F.,Smith, Peter J.,Chan, Wing-Chi,Haynes, Richard K.,Kotzé, Awie F.
, p. 260 - 266 (2011)
Artemisinins have low aqueous solubility that results in poor and erratic absorption upon oral administration. The poor solubility and erratic absorption usually translate to low bioavailability. Artemisinin-based monotherapy and combination therapies are
Evaluation and optimization of synthetic routes from dihydroartemisinin to the alkylamino-artemisinins artemiside and artemisone: A test of N-glycosylation methodologies on a lipophilic peroxide
Chan, Wing Chi,Wai Chan, Dennis Ho,Lee, Kin Wo,Tin, Wing Shan,Wong, Ho Ning,Haynes, Richard K.
, p. 5156 - 5171 (2018)
10-Alkylamino-artemisinins including artemiside and artemisone display enhanced activities against malaria. Earlier, dihydroartemisinin (DHA) TMS ether was converted by trimethylsilyl bromide into the 10-β-bromide that with amine nucleophiles provided the amino-artemisinins. In an attempt to develop more economic approaches, direct N-glycosylation of DHA was examined but 2-deoxyartemisinin was invariably obtained. However, hydroxyl group activation by conversion into the 10β-halide in non-polar solvents with anhydrous HCl and Group I and II metal halides, oxalyl chloride or thionyl chloride with catalytic DMSO, and oxalyl bromide did succeed. The β-halides were converted in situ by thiomorpholine into artemiside, and by thiomorpholine-1,1-dioxide into artemisone respectively in scalable reactions. Hydrogen peroxide-acetonitrile or the urea-hydrogen peroxide complex efficiently oxidized the sulfide artemiside to the sulfone artemisone. Overall, a generalized approach to 10-alkylamino-artemisinins is now available.
Artemisone - A highly active antimalarial drug of the artemisinin class
Haynes, Richard K.,Fugmann, Burkhard,Stetter, Joerg,Rieckmann, Karl,Heilmann, Hans-Dietrich,Chan, Ho-Wai,Cheung, Man-Ki,Lam, Wai-Lun,Wong, Ho-Ning,Croft, Simon L.,Vivas, Livia,Rattray, Lauren,Stewart, Lindsay,Peters, Wallace,Robinson, Brian L.,Edstein, Michael D.,Kotecka, Barbara,Kyle, Dennis E.,Beckermann, Bernhard,Gerisch, Michael,Radtke, Martin,Schmuck, Gabriele,Steinke, Wolfram,Wollborn, Ute,Schmeer, Karl,Roemer, Axel
, p. 2082 - 2088 (2007/10/03)
Artemisinin - the next generation: Efficacies of artemisone against the malaria parasite are substantially greater than those of the current artemisinin "gold standard", artesunate. Also, in contrast to most current artemisinins it displays low lipophilic
