63126-47-6Relevant articles and documents
Synthesis of 7-halogenated isatin sulfonamides: Nonradioactive counterparts of caspase-3/-7 inhibitor-based potential radiopharmaceuticals for molecular imaging of apoptosis
Limpachayaporn, Panupun,Wagner, Stefan,Kopka, Klaus,Schober, Otmar,Sch?fers, Michael,Haufe, Günter
, p. 9383 - 9395 (2014)
N-Alkylated (S)-7-halogen-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatins were developed as a new group of nonradioactive reference compounds for future radiotracers. Inhibitor potency studies of these compounds suggest that the binding pockets readily accommodate both the 7-halogen substituents and aliphatic side chains (methyl to n-butyl) as well as some ω-fluorinated analogues (3-fluoropropyl and 4-fluorobutyl) at the isatin nitrogen. Indeed, compared to the halogen free parent compounds, some 7-halogenated derivatives exhibited slightly improved inhibitory potencies with IC50 values up to 2.6 nM (caspase-3) and 3.3 nM (caspase-7), respectively. Moreover, the 7-position of isatin, a potential cytochrome P450 hydroxylation site, was substituted by I, Br, Cl, and F to potentially enhance the metabolic stability of isatin sulfonamides. As an example, the radiotracer [18F]39 that was produced by 19F/18F isotope exchange was shown to be stable in human blood serum after incubation at 37 °C for at least 90 min.
Orthogonal Catalysis for an Enantioselective Domino Inverse-Electron Demand Diels?Alder/Substitution Reaction
Ahles, Sebastian,Beeck, Sebastian,Wegner, Hermann A.
, (2021/12/09)
An enantioselective domino process for the synthesis of substituted 1,2-dihydronaphthalenes has been developed by the combination of chiral amines and a bidentate Lewis acid in an orthogonal catalysis. This new method is based on an inverse electron-demand Diels?Alder and a subsequent group exchange reaction. An enamine is generated in situ from an aldehyde and a chiral secondary amine catalyst that reacts with phthalazine, activated by the coordination to a bidentate Lewis acid catalyst. The absolute configuration of the product is controlled by chiral information provided by the amine. The formed ortho-quinodimethane intermediate is then transformed via a group exchange reaction with thiols. The new method shows a broad scope and tolerates a wide range of functional groups with enantiomeric ratios up to 91 : 9. All-in-all, this enantioselective synthesis tool provides an easy access to complex 1,2-dihydronaphthalenes starting from readily available phthalazine, aldehydes and thiols in a combinatorial way.
A New Class of C2-Symmetric Chiral Cyclopentadienyl Ligand Derived from Ferrocene Scaffold: Design, Synthesis and Application
Liang, Hao,Vasamsetty, Laxmaiah,Li, Teng,Jiang, Jijun,Pang, Xingying,Wang, Jun
supporting information, p. 14546 - 14550 (2020/10/15)
A new class of C2-symmetric, chiral cyclopentadienyl ligand based on planar chiral ferrocene backbone was developed. A series of its corresponding rhodium(I), iridium(I), and ruthenium(II) complexes were prepared as well. In addition, the rhodium(I) complexes were evaluated in the asymmetric catalytic intramolecular amidoarylation of olefin-tethered benzamides via C?H activation.
