931-46-4Relevant articles and documents
Design, synthesis and pharmacological evaluation of hybrid molecules out of quinazolinimines and lipoic acid lead to highly potent and selective butyrylcholinesterase inhibitors with antioxidant properties
Decker, Michael,Kraus, Birgit,Heilmann, Joerg
, p. 4252 - 4261 (2008)
A set of hybrid molecules were synthesized out of lipoic acid, α,ω-diamines of different lengths serving as spacers, and cholinesterase (ChE) inhibiting [2,1-b]quinazolinimines. Depending on the length of the alkylene spacer the amide hybrids are inhibitors of acetylcholinesterase (AChE) with inhibitory activities of 0.5-4.6 μM and inhibitors of butyrylcholinesterase (BChE) with activities down to 5.7 nM, therefore greatly exceeding the inhibitory activities of the parent quinazolinimines by factors of up to 1000. Due to increasing activity at BChE with increasing length of the alkylene spacer ～100-fold selectivity toward BChE is reached with a hepta- and an octamethylene spacer. Kinetic measurements reveal competitive and reversible inhibition of both ChEs by the hybrids. Furthermore, cell viability and antioxidant activity (using the ORAC-fluorescein assay) of several hybrids were evaluated, showing cytotoxicity at concentrations from 3.7 to 10.2 μM and antioxidant properties are in the range of 0.4-0.8 Trolox equivalents (lipoic acid = 0.6).
Direct NHC-catalysed redox amidation using CO2 for traceless masking of amine nucleophiles
Davidson, Robert W. M.,Fuchter, Matthew J.
supporting information, p. 11638 - 11641 (2016/10/04)
The N-heterocyclic carbene (NHC)-catalysed redox amidation reaction is poorly developed and usually requires catalytic co-additives for electron-rich amine nucleophiles. We report a masking strategy (using CO2) that couples release of the free amine nucleophile to catalytic turnover, and in doing so, enables direct catalytic redox amidation of electron-rich amines.
Modular routes towards new N,O-bidentate ligands containing an electronically delocalised β-enaminone chelating backbone
Beckmann, Udo,Eichberger, Eva,Lindner, Monika,Bongartz, Melanie,Kunz, Peter C.
supporting information; experimental part, p. 4139 - 4147 (2009/04/11)
Polyketones are synthesised by a transition-metal-catalysed copolymerisation of olefins and carbon monoxide. Nickel complexes with N,O-chelating ligands turned out to be promising catalysts in that field. In this work a series of new N,O ligands with an electronically delocalised β-enaminone backbone were synthesised and fully characterised. The ligand design was inspired by the ligand found in the most efficient nickel catalyst for polyketone synthesis and developed to a highly modular LEGO-like arsenal of reactions to versatile substituted β-enaminone ligands. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
