39964-87-9Relevant academic research and scientific papers
Structure-based design, synthesis, and biological studies of new anticancer norindenoisoquinoline topoisomerase i inhibitors
Song, Yunlong,Shao, Zhiyu,Dexheimer, Thomas S.,Scher, Evan S.,Pommier, Yves,Cushman, Mark
, p. 1979 - 1989 (2010)
On the basis of the superimposition of the crystal structures of norindenoisoquinoline 5 and topotecan (2) bound in the topoisomerase I-DNA covalent complex, as well as molecular docking and quantum chemical calculations, the substituted norindenoisoquino
Synthesis of 1,2-Dihydroisoquinolines by a Modified Pomeranz-Fritsch Cyclization
Ji, Xiang,Huang, Zheng,Lumb, Jean-Philip
, p. 1062 - 1072 (2020/01/31)
Isoquinolines (IQs) and their derivatives are present in many natural products and biologically active small molecules. Herein, we report a modified procedure for the classical Pomeranz-Fritsch protocol, which expands the scope of 1,2-dihydroisoquinoline (DHIQ) products. 1,2-DHIQs are an attractive branch point for the synthesis of IQs, but because of their innate reactivity, they have remained difficult to prepare. We demonstrate that the Fujioka/Kita conditions, combining trimethylsiyltriflate (TMSOTf) and an amine base, activate dimethylacetals required for Pomeranz-Fritsch cyclization under sufficiently mild conditions to prepare a broad range of 1,2-DHIQ products. We also demonstrate the synthetic value of these DHIQs by further functionalization to either reduced tetrahydroisoquinoline (THIQ) or fully aromatized IQ natural products.
One substrate, two modes of C-H functionalization: A metal-controlled site-selectivity switch in C-H arylation reactions
Tiwari, Virendra Kumar,Kamal, Neha,Kapur, Manmohan
supporting information, p. 262 - 265 (2017/11/27)
A unique site-selectivity switch has been achieved in the ruthenium-catalyzed C-H arylation reaction of N-acetyl-1,2-dihydroisoquinolines. This metal-mediated switch is antipodal to the previous report on the palladium-mediated C-4 C-H arylation on the same substrate. Mechanistic details reveal interesting aspects of the reaction pathway, and kinetic studies bring out the difference in the modes of C-H activation adopted by the two catalytic systems.
An efficient Ugi-3CR/aza Diels-Alder/Pomeranz-Fritsch protocol towards novel aza-analogues of (±)-nuevamine, (±)-lennoxamine and magallanesine: a diversity oriented synthesis approach
Vázquez-Vera, óscar,Sánchez-Badillo, Jorge S.,Islas-Jácome, Alejandro,Rentería-Gómez, Manuel A.,Pharande, Shrikant G.,Cortes-García, Carlos J.,Rincón-Guevara, Mónica A.,Ibarra, Ilich A.,Gámez-Monta?o, Rocío,González-Zamora, Eduardo
supporting information, p. 2363 - 2369 (2017/03/20)
A rapid and efficient synthesis of a series of (±)-nuevamine, (±)-lennoxamine and magallanesine aza analogues is described. The synthetic strategy involves Ugi-3CR and two further condensation processes, aza-Diels-Alder cycloaddition and the Pomeranz-Fritsch reaction. The variation of the chain-size in aldehyde moieties provided structural diversity in only two operational reaction steps.
SUBSTITUTED NORINDENOISOQUINOLINES, SYNTHESES THEREOF, AND METHODS OF USE
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Page/Page column 32; 36, (2011/08/21)
Described herein are substituted norindenoisoquinoline compounds, and pharmaceutical compositions and formulations comprising the norindenoisoquinoline compounds. Also described herein are methods for using the compounds for the treatment and/or preventio
Synthesis of Indenoisoquinoliniums and Methods of Use
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Page/Page column 10, (2008/12/07)
Substituted indenoisoquinolinium compounds, and pharmaceutical formulations of substituted indenoisoquinolinium compounds are described. Also described are processes for preparing substituted indenoisoquinolinium compounds. Also described are methods for
Potent and selective xanthine-based inhibitors of phosphodiesterase 5
Arnold, Nichola J.,Arnold, Ruth,Beer, David,Bhalay, Gurdip,Collingwood, Stephen P.,Craig, Sarah,Devereux, Nicholas,Dodds, Mark,Dunstan, Andrew R.,Fairhurst, Robin A.,Farr, David,Fullerton, Joseph D.,Glen, Angela,Gomez, Sylvie,Haberthuer, Sandra,Hatto, Julia D.I.,Howes, Colin,Jones, Darryl,Keller, Thomas H.,Leuenberger, Beate,Moser, Heinz E.,Muller, Irene,Naef, Reto,Nicklin, Paul A.,Sandham, David A.,Turner, Katharine L.,Tweed, Morris F.,Watson, Simon J.,Zurini, Mauro
, p. 2376 - 2379 (2007/10/03)
Inhibitors of PDE5 are useful therapeutic agents for treatment of erectile dysfunction. A series of novel xanthine derivatives has been identified as potent inhibitors of PDE5, with good levels of selectivity against other PDE isoforms, including PDE6. St
Synthesis and mechanism of action studies of a series of norindenoisoquinoline topoisomerase I poisons reveal an inhibitor with a flipped orientation in the ternary DNA-enzyme-inhibitor complex as determined by X-ray crystallographic analysis
Ioanoviciu, Alexandra,Antony, Smitha,Pommier, Yves,Staker, Bart L.,Stewart, Lance,Cushman, Mark
, p. 4803 - 4814 (2007/10/03)
Several norindenoisoquinolines substituted with methoxy or methylenedioxy groups have been prepared and their anticancer properties evaluated in cancer cell cultures and in topoisomerase I inhibition assays. 2,3-Dimethoxy-8,9- methylenedioxy-11H-indeno[1,
