33588-64-6Relevant articles and documents
Tandem reorganisation of 1,3-dipolar cycloadducts of C-(4-oxo- 4H[1]benzopyran-3-yl)-N-phenylnitrone and allenic esters, leading to novel functionalized benzo[b]indolizines
Ishar,Kumar, Kamal
, p. 175 - 176 (1999)
C-(4-oxo-4H[1]benzopyran-3-yl)-N-phenylnitrone (1) adds regiospecifically to the C2-C3 π-bond of allenic esters (2a-c) and the 1,3-dipolar cycloadducts formed undergo a series of intramolecular reorganisations including an intramolecular (4+2) cycloaddition, in situ, to yield novel functionalized benzo[b]indolizines (3a-c) in good yields.
Synthesis and SAR of Tetracyclic Inhibitors of Protein Kinase CK2 Derived from Furocarbazole W16
Borgert, Sebastian,Daniliuc, Constantin G.,Ensan, Deeba,Jose, Joachim,Kr?ger, Lukas,Lauwers, Miriam,Nienberg, Christian,Pietsch, Markus,Steinkrüger, Michaela,Wünsch, Bernhard
supporting information, p. 871 - 881 (2020/05/06)
The serine/threonine kinase CK2 modulates the activity of more than 300 proteins and thus plays a crucial role in various physiological and pathophysiological processes including neurodegenerative disorders of the central nervous system and cancer. The enzymatic activity of CK2 is controlled by the equilibrium between the heterotetrameric holoenzyme CK2α2β2 and its monomeric subunits CK2α and CK2β. A series of analogues of W16 ((3aR,4S,10S,10aS)-4-{[(S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-10-(3,4,5-trimethoxyphenyl)-4,5,10,10a-tetrahydrofuro[3,4-b]carbazole-1,3(3aH)-dione ((+)-3 a)) was prepared in an one-pot, three-component Levy reaction. The stereochemistry of the tetracyclic compounds was analyzed. Additionally, the chemically labile anhydride structure of the furocarbazoles 3 was replaced by a more stable imide (9) and N-methylimide (10) substructure. The enantiomer (?)-3 a (Ki=4.9 μM) of the lead compound (+)-3 a (Ki=31 μM) showed a more than sixfold increased inhibition of the CK2α/CK2β interaction (protein-protein interaction inhibition, PPII) in a microscale thermophoresis (MST) assay. However, (?)-3 a did not show an increased enzyme inhibition of the CK2α2β2 holoenzyme, the CK2α subunit or the mutated CK2α′ C336S subunit in the capillary electrophoresis assay. In the pyrrolocarbazole series, the imide (?)-9 a (Ki=3.6 μM) and the N-methylimide (+)-10 a (Ki=2.8 μM) represent the most promising inhibitors of the CK2α/CK2β interaction. However, neither compound could inhibit enzymatic activity. Unexpectedly, the racemic tetracyclic pyrrolocarbazole (±)-12, with a carboxy moiety in the 4-position, displays the highest CK2α/CK2β interaction inhibition (Ki=1.8 μM) of this series of compounds.
Photocatalytic Alkylation of Pyrroles and Indoles with α-Diazo Esters
Ciszewski, Lukasz W.,Durka, Jakub,Gryko, Dorota
supporting information, p. 7028 - 7032 (2019/09/12)
This article describes the photoalkylation of electron-rich aromatic compounds with diazo esters. C-2-alkylated indoles and pyrroles are obtained with good yields even though the photocatalyst loading is as low as 0.075 mol %. For EWG-substituted substrates, the addition of a catalytic amount of N,N-dimethyl-4-methoxyaniline is required. Both EWG-EWG- and EWG-EDG-substituted diazo esters are suitable as alkylating agents. The reaction selectivity and mechanistic experiments suggest that carbenes/carbenoid intermediates are not involved in the reaction pathway.
