139214-38-3Relevant academic research and scientific papers
Optimisation of the allylsilane approach to C-10 deoxo carba analogues of dihydroartemisinin: Synthesis and in vitro antimalarial activity of new, metabolically stable C-10 analogues
O'Neill,Pugh,Stachulski,Ward,Davies,Kevin Park
, p. 2682 - 2689 (2001)
An optimised protocol has been developed for the coupling of dihydroartemisinin benzoate with a range of aromatic allylsilanes to provide a number of new C-10 deoxo derivatives (11a-11g) in yields ranging from 70 to 94%. These compounds were up to ten times more potent than artemisinin in in vitro tests against the chloroquine resistant K1 strain of Plasmodium falciparum. Ferrous mediated degradation of these analogues produces as the main product, a dicarbonyl formate 12, which is not seen when the same reaction is carried out with artemisinin or artemether. This finding may indicate that analogues in this class have a subtly different "antimalarial" mechanism of action.
The Effect of the Ring Size of the Dithiolato Leaving Group on the Orientation of β-Elimination in the Nickel-catalysed Alkenation of Cyclic Dithioacetals with Me3SiCH2MgCl
Wong, Ken-Tsung,Ni, Zhi-Jie,Luh, Tien-Yau
, p. 3113 - 3116 (2007/10/02)
The product distribution (allyl- vs. vinyl-silanes) of the reactions of dithioacetals derived from alkyl aryl ketones with Me3SiCH2MgCl surprisingly depends on ring size of the cyclic dithioacetals, the five-membered ring substrates affording allylsilane as the major product while the six-membered analogues yield vinylsilanes predominantly.These results indicate that the leaving group, dithiolato moiety, may remain coordinated to the metal centre during the course of the catalytic process.
