1415975-88-0Relevant articles and documents
Chemoselective flow hydrogenation approaches to isoindole-7-carboxylic acids and 7-oxa-bicyclio[2.2.1]heptanes
Hizartzidis,Tarleton,Gordon,McCluskey
, p. 9709 - 9722 (2014/03/21)
Two libraries of highly decorated norcantharidin analogues were accessed via a series of sequential chemoselective flow hydrogenations and solvent-free transformations. Utilising a 10% Pd/C catalyst, modifications to reaction parameters (H2 pressure, temperature and flow rate conditions) allowed facile access to effect selective direct reductive aminations and olefin reductions in the presence of furan, benzyl and nitrile moieties were established. The use of 20% Pd(OH)2/C; Pd tetrakis; 5% Pt/C (sulfided) gave mixtures of furan and olefin (both reduced) and olefin reduced products. RuO2; 0.5% Re/C and Re2O7 resulted in no reduction. Concurrent olefin and nitrile reduction was achieved in the presence of furan moieties by employing a RANEY nickel catalyst. In total, 31 reaction conditions were examined using less than 200 mg of reagents allowing optimised conditions to be efficiently determined. These optimised hydrogenation conditions afforded desired analogues in near quantitative yields thus removing the requirements of reaction workup and chromatography.
Focused library development of 2-phenylacrylamides as broad spectrum cytotoxic agents
Tarleton, Mark,Dyson, Lauren,Gilbert, Jayne,Sakoff, Jennette A.,McCluskey, Adam
, p. 333 - 347 (2013/02/22)
With our lead compound (E)-3-(4-chlorophenyl)-2-(1H-pyrrole-2-carbonyl) acrylonitrile (1) inducing 50% growth inhibition of 11 cancer cell lines at 27-61 μM, potency enhancements were rapidly established through the synthesis of a series of focused compou
