30059-39-3Relevant academic research and scientific papers
Superacid synthesis of halogen containing N-substituted-4-aminobenzene sulfonamides: New selective tumor-associated carbonic anhydrase inhibitors
Compain, Guillaume,Martin-Mingot, Agnes,Maresca, Alfonso,Thibaudeau, Sebastien,Supuran, Claudiu T.
, p. 1555 - 1563 (2013/04/10)
A series of new, halogen containing N-substituted 4- aminobenzenesulfonamides were synthesized by using superacid HF/SbF5 chemistry and investigated as inhibitors of several human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, that is, the cytosolic hCA I and II and, the tumor-associated transmembrane isoforms hCA IX and XII. Despite the substitution of the sulfonamide function, the presence of fluorine atom(s) in β position of the sulfonamide function strongly favors hCA inhibition. A similar effect of the β-fluorinated alkyl substitution on the amino function has been also observed. Among the tested compounds, several chlorinated derivatives have been identified as selective nanomolar, tumor-associated isoforms inhibitors. These non-primary sulfonamides probably bind in the coumarin-binding site, at the entrance of the cavity, and not to the metal ion as the primary sulfonamide inhibitors.
Selective anti-markovnikov cyclization and hydrofluorination reaction in superacid HF/SbF5: A tool in the design of nitrogen-containing (fluorinated) polycyclic systems
Compain, Guillaume,Bonneau, Celine,Martin-Mingot, Agnes,Thibaudeau, Sebastien
, p. 4463 - 4472 (2013/06/05)
The selective synthesis of tetrahydroquinolines and fluorinated arylamines was performed in superacid HF/SbF5 through a superelectrophilic ammonium-carbenium activation process. This anti-Markovnikov oriented reaction was applied to the straightforward synthesis of highly valued (fluorinated) nitrogen-containing heterocyclic compounds.
Anti-Markovnikov additions to N-allylic derivatives involving ammonium-carbenium superelectrophiles
Compain, Guillaume,Martin-Mingot, Agnes,Frapper, Gilles,Bachmann, Christian,Jouannetaud, Marie-Paule,Thibaudeau, Sebastien
supporting information; experimental part, p. 5877 - 5879 (2012/08/14)
Anti-Markovnikov additions to non-conjugated unsaturated amines in superacid are reported. In situ NMR studies, DFT calculations and labelled substrates reactions support the involvement of new ammonium-carbenium superelectrophiles in this original proces
Small molecule modifiers of MicroRNA miR-122 function for the treatment of hepatitis C Virus infection and hepatocellular carcinoma
Young, Douglas D.,Connelly, Colleen M.,Grohmann, Christoph,Deiters, Alexander
supporting information; experimental part, p. 7976 - 7981 (2010/08/05)
MicroRNAs are a recently discovered new class of important endogenous regulators of gene function. Aberrant regulation of microRNAs has been linked to various human diseases, most importantly cancer. Small molecule intervention of microRNA misregulation h
