10432-39-0Relevant articles and documents
Solvent-free condensations of ketones with malononitrile catalysed by methanesulfonic acid/morpholine system
Gora,Kozik,Jamrozy,Luczynski,Brzuzan,Wozny
, p. 863 - 867 (2009)
The preparation of ylidenemalononitriles via Knoevenagel condensations of ketones with malononitrile under solvent-free conditions is described. Good yields and short reaction time are the features observed with methanesulfonic acid (MSA)/morpholine used as the catalyst. The wide applicability of the protocol is shown by the fact that not only unconjugated, but also aryl-alkyl ketones gave satisfactory yields.
Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds
Wu, Hui-Chun,Wang, Chen,Chen, Ying-Han,Liu, Yan-Kai
supporting information, p. 1762 - 1765 (2021/02/27)
An organocatalytic vinylogous Michael addition triggered triple-cascade reaction has been developed. 2-Hydroxycinnamaldehydes worked under iminium activation with either acyclic or cyclic ketone-derived α,α-dicyanoalkenes, yielding the benzofused oxabicyclo[3.3.1]nonanes bearing one quaternary stereocenter with excellent stereoselectivities.
INHIBITORS OF THE PD-1/PD-L1 PROTEIN/PROTEIN INTERACTION
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Page/Page column 36, (2017/08/01)
The present invention provides novel compounds of formula (I) that are useful as inhibitors of the PD-1/PD-L1 protein/protein interaction.
Synthesis and bioactivity of novel amino-pyrazolopyridines
Orlikova, Barbora,Chaouni, Wafaa,Schumacher, Marc,Aadil, Mina,Diederich, Marc,Kirsch, Gilbert
, p. 450 - 457 (2014/09/03)
Here we describe the synthesis and biological activity of novel amino-pyrazolopyridines with anti-NF-κB and pro-apoptotic potential. α-Methylene ketones were used as a starting point for synthesis of amino-pyrazolopyridine 3. The alkylidene malononitriles 1 were obtained by the Knoevenagel reaction of ketones with malononitriles. Vilsmeier-Haack reaction allowed direct access to 2-chloro-3-cyanopyridines 2. Those products, by refluxing with hydrazine hydrate, allowed cyclization to amino-pyrazolopyridines 3a-g, which were not previously described in the literature. Bioactivity results indicated that amino-pyrazolopyridines 3a, 3b and 3g induced apoptotic cell death in K562 cancer cells with an IC50 of 36.5 ± 3.9 μM, 27.6 ± 4.5 μM and 35.0 ± 2.3 μM, respectively, after 72 h. In addition, compounds 3a, 3b and 3g exerted NF-κB inhibition activity with an IC50 of 4.7 ± 1.6 μM, 6.9 ± 1.9 μM and 39.8 ± 3.9 μM, respectively, after 8 h in K562 cells activated with TNFα. Compounds 3b and 3g showed interesting differential toxicity as viability of peripheral blood mononuclear cells (PBMCs) from healthy donors remained largely unaffected by this treatment.