30059-39-3Relevant articles and documents
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.
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
