16721-45-2Relevant articles and documents
Efficient access to novel furanofurone compounds from quinic acid: Studies of inter-and intramolecular Wittig reactions on lactones
Baptistella, Lúcia Helena Brito,Jorge, André De Carvalho
, p. 3045 - 3049 (2007)
(-)-Quinic acid has been converted into derivatives of a furo[3,2-b]furan-2-one system using Wittig olefination reactions of lactones. Studies for this transformation included the use of microwave-assisted reactions. Georg Thieme Verlag Stuttgart.
Novel photocyclization of β,γ-unsaturated oximes
Armesto, Diego,Ramos, Ana,Ortiz, Maria J.,Mancheno, Maria J.,Mayoral, Elena P.
, p. 514 - 516 (1995)
Previously, β,γ-unsaturated oximes were thought to be photochemically unreactive.The present study reports the first three examples of photocyclization of β,γ-unsaturated ketoximes to yield 4,5-dihydroisoxazole derivatives.Typically, acetophenone-sensitiz
Ylide-Stabilized Phosphenium Cations: Impact of the Substitution Pattern on the Coordination Chemistry
Stalder, Tobias,Krischer, Felix,Steinert, Henning,Neigenfind, Philipp,Gessner, Viktoria H.
, (2022/01/11)
Although N-heterocyclic phosphenium (NHP) cations have received considerable research interest due to their application in organocatalysis, including asymmetric synthesis, phosphenium cations with other substitution patterns have hardly been explored. Her
Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters
Frydrych, Ivo,Urban, Milan,?arek, Jan,Benická, Sandra,D?ubák, Petr,Gurská, Soňa,Hajdúch, Marián,Kotulová, Jana,Li?ková, Barbora,Olejníková, Denisa,Pokorny, Jan
, (2021/07/28)
A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.
Silver-Catalysed Hydroarylation of Highly Substituted Styrenes
Dalton, Toryn,Gre?ies, Steffen,Das, Mowpriya,Niehues, Maximilian,Schrader, Malte L.,Gutheil, Christian,Ravoo, Bart Jan,Glorius, Frank
supporting information, p. 8537 - 8541 (2021/03/16)
Hydroarylation is an effective strategy to rapidly increase the complexity of organic structures by transforming flat alkene moieties into three-dimensional frameworks. Many strategies have already been developed to achieve the hydroarylation of styrenes,
