Optimisation of the allylsilane approach to C-10 deoxo carba analogues of dihydroartemisinin: synthesis and in vitro antimalarial activity of new, metabolically stable C …

PM O'Neill, M Pugh, AV Stachulski, SA Ward…

Index: O'Neill; Pugh; Stachulski; Ward; Davies; Kevin Park Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 20 p. 2682 - 2689

Full Text: HTML

Citation Number: 26

Abstract

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 ...

Related Articles:

Catalytic, enantioselective alkylation of α-imino esters: The synthesis of nonnatural α-amino acid derivatives

[Ferraris; Young; Cox; Dudding; Drury III; Ryzhkov; Taggi; Lectka Journal of the American Chemical Society, 2002 , vol. 124, # 1 p. 67 - 77]

Synthesis and reactivity of [18F]-N-fluorobenzenesulfonimide

[Teare, Harriet; Robins, Edward G.; Arstad, Erik; Luthra, Sajinder K.; Gouverneur, Veronique Chemical Communications, 2007 , # 23 p. 2330 - 2332]

Ionic liquid-promoted, highly regioselective Heck arylation of electron-rich olefins by aryl halides

[Mo, Jun; Xu, Lijin; Xiao, Jianliang Journal of the American Chemical Society, 2005 , vol. 127, # 2 p. 751 - 760]

Cobalt-catalyzed trimethylsilylmethylmagnesium-promoted radical alkenylation of alkyl halides: A complement to the heck reaction

[Affo, Walter; Ohmiya, Hirohisa; Fujioka, Takuma; Ikeda, Yousuke; Nakamura, Tomoaki; Yorimitsu, Hideki; Oshima, Koichiro; Imamura, Yuki; Mizuta, Tsutomu; Miyoshi, Katsuhiko Journal of the American Chemical Society, 2006 , vol. 128, # 24 p. 8068 - 8077]

The effect of added silver nitrate on the palladium-catalyzed arylation of allyltrimethylsilanes

[Karabelas, Kostas; Westerlund, Christer; Hallberg, Anders Journal of Organic Chemistry, 1985 , vol. 50, # 20 p. 3896 - 3900]

More Articles...