40359-45-3Relevant academic research and scientific papers
Efficient combination of task-specific ionic liquid and microwave dielectric heating applied to one-pot three component synthesis of a small library of 4-thiazolidinones
Fraga-Dubreuil, Joan,Bazureau, Jean Pierre
, p. 6121 - 6130 (2003)
The first report of the use of task-specific ionic liquid as synthetic equivalent of ionic liquid-phase matrice for the preparation of a small library of 4-thiazolidinones is reported in this paper. The starting (ethyleneglycol)ionic liquid-phase is funct
Discovery and optimisation of potent, selective, ethanolamine inhibitors of bacterial phenylalanyl tRNA synthetase
Jarvest, Richard L.,Erskine, Symon G.,Forrest, Andrew K.,Fosberry, Andrew P.,Hibbs, Martin J.,Jones, Joanna J.,O'Hanlon, Peter J.,Sheppard, Robert J.,Worby, Angela
, p. 2305 - 2309 (2007/10/03)
High throughput screening of Staphylococcus aureus phenylalanyl tRNA synthetase (FRS) identified ethanolamine 1 as a sub-micromolar hit. Optimisation studies led to the enantiospecific lead 64, a single-figure nanomolar inhibitor. The inhibitor series shows selectivity with respect to the mammalian enzyme and the potential for broad spectrum bacterial FRS inhibition.
Grafted ionic liquid-phase-supported synthesis of small organic molecules
Fraga-Dubreuil, Joan,Bazureau, Jean Pierre
, p. 6097 - 6100 (2007/10/03)
The preparation and applications in the Knoevenagel and 1,3-dipolar cycloaddition reactions of new grafted soluble liquid phases derived from imidazolium ionic liquids are described. Good yields and high regioselectivity are the features observed with these unconventional liquid phases.
Catalytic Cyclophanes. Part VIII. Cytochrome P-450 Activity of a Porphyrin-Bridged Cyclophane
Benson, David R.,Valentekovich, Robert,Tam, Suk-Wah,Diederich, Francois
, p. 2034 - 2060 (2007/10/02)
Following a known synthetic procedure, the porphyrin-cyclophane 1 having a porphyrin attached by two straps to an apolar cyclophane binding site was prepared.Upon metallation, the ZnII and FeIII derivatives 2 and 3, respectively, were obtained in good yields.Treatment of 3 with base yielded the μ-oxo dimer 4 in which the two oxo-bridged porphyrins moieties are both capped by cyclophane binding sites.All compounds 1-4 are freely soluble in protic solvents such as MeOH and CF3CH2OH, and the FIII derivatives 3 and 4 are active cytochrome P-450 mimics in these protic environments.Strong inclusion complexation of polycyclic aromatic hydrocarbons by 1 and 3 in alcoholic solvents was observed and quantified by 1H-NMR and UV/VIS titrations.Acenaphthylene binds in an 'equatorial' orientation which locates its reactive 1,2-double bond near the porphyrin center, whereas phenanthrene binds 'axially' with the reactive 9,10-double bond oriented away from the porphyrin.The reduction potential of 3 was not significantly altered by substrate binding.In the unbound form, the FeIII center in porphyrin 3 was found by ESR and 1H-NMR to prefer a high-spin state (S = 5/2).In CF3CH2OH, using iodosylbenzene as O-transfer agent, the FeIII derivative 3 catalyzed the oxidation of acenaphthylene to acenaphthen-1-one (14).Phenanthrene inhibited the reaction, possibly as a result of strong but nonproductive binding.Under similar conditions, isotetralin (18) was aromatized with high turnover to 1,4-dihydronaphthalene.The μ-oxo dimer 4 also showed high catalytic activity in the oxidation of acenaphthylene in MeOH, a result which provides strong evidence for efficient supramolecular catalysis.Due to as yet unknown reaction channels leading to polymeric products, poor mass balances were generally obtained in the oxidations effected in MeOH and CF3CH2OH in the presence of PhIO.
