46926-59-4Relevant academic research and scientific papers
Identification of selective inhibitors of sphingosine kinases 1 and 2 through a structure–activity relationship study of 4-epi-jaspine B
Ohno, Hiroaki,Honda, Maho,Hamada, Naoka,Miyagaki, Jun,Iwata, Akira,Otsuki, Kazuhiro,Maruyama, Toru,Nakamura, Shinya,Nakanishi, Isao,Inuki, Shinsuke,Fujii, Nobutaka,Oishi, Shinya
, p. 3046 - 3052 (2017/05/29)
We recently reported that 4-epi-jaspine B exhibits potent inhibitory activity towards sphingosine kinases (SphKs). In this study, we investigated the effects of modifying the 2-alkyl group, as well as the functional groups on the THF ring of 4-epi-jaspine B using a diversity-oriented synthesis approach based on a late-stage cross metathesis reaction. The introduction of a p-phenylene tether to the alkyl group was favored in most cases, whereas the replacement of a carbon atom with an oxygen atom led to a decrease in the inhibitory activity. Furthermore, the introduction of a bulky alkyl group at the terminus led to a slight increase in the inhibitory activity of this series towards SphKs compared with 4-epi-jaspine B (the Q values of compound 13 for SphK1 and SphK2 were 0.2 and 0.4, respectively). Based on this study, we identified two isoform selective inhibitors, including the m-phenylene derivative 4 [IC50 (SphK1) ≥30?μM; IC50 (SphK2)?=?2.2?μM] and the methyl ether derivative 22 [IC50 (SphK1)?=?4.0?μM; IC50 (SphK2) ≥30?μM].
Olefin-assisted iron-catalyzed alkylation of aryl chlorides
Guelak, Samet,Gieshoff, Tim N.,Von Wangelin, Axel Jacobi
, p. 2197 - 2202 (2013/10/01)
A selective and operationally simple ironcatalyzed cross-coupling of aryl chlorides with alkylmagnesium halides has been developed. The reaction tolerates various functional groups and exhibits high chemoselectivity even in the presence of aryl bromides. Mechanistic studies indicate the essential role of the olefin substituent for substrate activation. Competing polymerization and reduction are effectively suppressed.
NOVEL METHOD FOR PREPARING STYRENIC OLEFINS
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Page/Page column 13, (2008/06/13)
The present invention relates to a method for preparing a styrenic olefin. The method of the present invention comprises the steps of: adding a catalyst and a solvent in a reactor and heating the reactor to create a reflux state; adding an alcohol starting material to the reactor dropwise at a constant rate; removing water generated by adding the alcohol starting material from the reactor; and purifying the obtained styrenic olefin. The method of the present invention is advantageous in minimizing byproducts and preparing styrenic olefins having a variety of substituents in high yield.
Syndiospecific synthesis of longer p-n-alkyl-substituted polystyrenes using monocyclopentadienyl-type titanium catalysts
Quirk, Roderic P.,Ok, Myung-Ahn
, p. 3976 - 3982 (2007/10/03)
Substituted styrenes with linear alkyl substituents (C6 to C12) at the para position on the ring were synthesized and polymerized using the (Me)5CpTi(OMe)3/MAO catalytic system. Increased polymerization activiti
