171243-35-9Relevant academic research and scientific papers
Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based inhibitors of Cyclin D1-CDK4: Synthesis, biological evaluation and structure-activity relationships. Part 2
Horiuchi, Takao,Nagata, Motoko,Kitagawa, Mayumi,Akahane, Kouichi,Uoto, Kouichi
experimental part, p. 7850 - 7860 (2010/04/02)
The design, synthesis and evaluation of novel thieno[2,3-d]pyrimidin-4-yl hydrazone analogues as cyclin-dependent kinase 4 (CDK4) inhibitor are described. Focusing on the optimization of the heteroaryl moiety at the hydrazone with substituted phenyl group
Acyl Transfer as a Problematic Side Reaction in Polymer-Supported Oligosaccharide Synthesis
Nukada, Tomoo,Berces, Attila,Whitfield, Dennis M.
, p. 9030 - 9045 (2007/10/03)
Under a wide variety of glycosylation conditions acyl transfer to the polymer support competed with glycoside formation, including the pivaloyl protecting group. As well as acyl transfer, many glycosylations also led to the formation of polymer-bound β-1,2-linked oligomers of the donor. Using ethyl 2,6-di-O-pivaloyl-3,4-O-isopropylidene-β-D-galactothiopyranoside as donor under promotion of N-iodosuccinimide/silver trifluoromethanesulfonate in the presence of 2-methyl-2-butene, an 82% yield of glycoside was obtained along with pivaloylated polymer. Subsequent work showed that increasing the steric bulk about the alcoholic acceptor in conjunction with this 2-O-pivaloyl-protected glycosyl donor completely suppresses this side reaction, giving a nearly quantitative yield of glycoside. This contraintuitive approach of decreasing the reactivity of both the donor and the acceptor to minimize a side reaction is rationalized by assuming that the barrier to acyl transfer is more sensitive to the protecting groups than that of glycosylation. These developments led to a polymer-supported synthesis of the branch point trisaccharide of the group B type 1A Streptococcus capsular polysaccharide.
Total Synthesis of Balanol and Designed Analogues
Nicolaou, K. C.,Koide, Kazunori,Bunnage, Mark E.
, p. 454 - 466 (2007/10/03)
The total synthesis of balanol, a potent protein kinase C inhibitor isolated from the fungus Verticillium balanoides, is described.The hexahydroazepine fragment was prepared from D-serine through a sequence of reactions including the diastereoselective allylboration of a derived amino aldehyde and a base-induced 7-exo-tet ring closure as key steps.The benzophenone fragment was secured through the initial coupling of the two functionalised aromatic components through an ester linkage, followed by intramolecular nucleophilic attack of an aryl lithium derivative to form the desired ketone bridge.After coupling of the two balanol domains, the adoption of benzyl-derived protecting groups for the latent functionalities then allowed the liberation of balanol in a single step by catalytic hydrogenolysis.Finally, the newly developed synthetic strategy was applied to the synthesis of a variety of designed balanol analogues for biological evaluation. - Keywords: antitumor agents, balanol, enzyme inhibitor, natural product, total synthesis
