17624-26-9Relevant academic research and scientific papers
A general catalytic hydroamidation of 1,3-dienes: Atom-efficient synthesis of N-allyl heterocycles, amides, and sulfonamides
Banerjee, Debasis,Junge, Kathrin,Beller, Matthias
supporting information, p. 1630 - 1635 (2014/03/21)
Transition-metal-catalyzed hydroamination reactions are sustainable and atom-economical C-N bond-forming processes. Although remarkable progress has been made in the inter- and intramolecular amination of olefins and 1,3-dienes, related intermolecular reactions of amides are still much less known. Control of the regioselectivity without analogous telomerization is the particular challenge in the catalytic hydroamidation of alkenes and 1,3-dienes. Herein, we report a general protocol for the hydroamidation of electron-deficient N-heterocyclic amides and sulfonamides with 1,3-dienes and vinyl pyridines in the presence of a catalyst derived from [{Pd(π-cinnamyl)Cl}2] and ligand L7 or L10. The reactions proceeded in good to excellent yield with high regioselectivity. The practical utility of our method is demonstrated by the hydroamidation of functionalized biologically active substrates. The high regioselectivity for linear amide products makes the procedure useful for the synthesis of a variety of allylic amides. Give me an N bond: A general palladium-catalyzed intermolecular hydroamidation of 1,3-dienes with electron-deficient N-heterocycles, amides, and sulfonamides proceeded with high regioselectivity for 1,4-addition and excellent functional-group tolerance (see scheme). The practical utility of the method was demonstrated by the hydroamidation of functionalized biologically active substrates. Copyright
The coordination chemistry of fluorescent pyridinyl- and quinolinyl-phthalimide ligands with the {AuI-PPh3} cationic unit
Mullice, Lucy A.,Thorp-Greenwood, Flora L.,Laye, Rebecca H.,Coogan, Michael P.,Kariuki, Benson M.,Pope, Simon J.A.
experimental part, p. 6836 - 6842 (2010/01/06)
The new mono-dentate ligands, 2-(2-aminoethyl)-N-phthalimido-pyridine (L4) and 8-amino-N-phthalimido-quinoline (L6), were synthesised using a solvent-free melt method. These ligands together with L 1-3,5 (3-amino-N-phthalimido-pyridine; 3-aminomethyl-N-phthalimido- pyridine; 4-aminomethyl-N-phthalimido-pyridine; 3-amino-N-phthalimido-quinoline) were then used to access six luminescent AuI complexes of the generic type {Ph3P-Au-Ln}(OTf). X-Ray crystallography has been used to structurally characterise three of the complexes showing that in the cases of L1 and L3 the complexes adopt an approximately linear P-Au-N coordination geometry. However, in the case of the sterically demanding L6 the structure shows distortions within the ligand and deviations from a linear coordination geometry. Solution state 1H and 31P{1H} NMR confirmed that the proposed formulations and coordination modes exist in solution. At room temperature the photophysical studies showed that the emission from each of the six complexes was in the visible region (395-475 nm) and assigned to a ligand-centred fluorescence (τ 10 ns) in each case. The Royal Society of Chemistry 2009.
Isoindolone compounds, compositions containing the same, and methods of use thereof for the treatment of viral infections related to the etiology of cancer
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Page/Page column 5, (2010/11/24)
Isoindolone derivatives, compositions containing the same, and methods of use thereof for the treatment or prophylaxis of viral infection are disclosed.
New anti-inflammatory N-pyridinyl(alkyl)phthalimides acting as tumour necrosis factor-α production inhibitors
Collin, Xavier,Robert, Jean-Michel,Wielgosz, Gaetane,Le Baut, Guillaume,Bobin-Dubigeon, Christine,Grimaud, Nicole,Petit, Jean-Yves
, p. 639 - 649 (2007/10/03)
This paper describes the synthesis of N-pyridinyl(alkyl)phthalimides related to N-phenyl-4,5,6,7-tetrafluorophthalimides known to be inhibitors of tumour necrosis factor-α (TNFα) production. Pharmacomodulation at the phthalimidic nitrogen led to the selection of two pharmacophoric fragments (2,4-lutidinyl and β-picolyl), allowing significant inhibition of TNFα production (compounds 12 and 17). Variation of the substituents linked to the homocycle of their phthalimide scaffold indicated that high (TNFα production) inhibitory potency could be achieved, notably by 5-fluoro, 4- or 5-nitro, 5-amino and especially tetrafluoro substitution. The most active compound, N-(pyridin-3-ylmethyl)-4,5,6,7-tetrafluorophthalimide (32) (84% inhibition at 10 μM), also produced an anti-oedematous effect in the PMA-induced mouse-ear swelling test. Although less active than dexamethasone, it exerted a marked reduction in ear thickness after oral administration (63% vs. 85% for dexamethasone at 0.2 mM kg-1) and remained efficient after topical application (46% vs. 96% for the dexamethasone). It also induced potent inhibition in the rat carrageenan foot oedema test with an ID50 (0.14 μM kg-1) comparable with that of N-(2,6-diisopropylphenyl)phthalimide (4) (0.15 μM kg-1).
Synthesis and potent tumour necrosis factor-α production inhibitory activity of N-pyridinylphthalimides and derivatives
Collin,Robert,Robert-Piessard,Le Baut,Bobin-Dubigeon,Vernhet,Lang,Petit
, p. 27 - 31 (2007/10/03)
A series of N-azaaryl(alkyl)phthalimides incorporating amino(alkyl)pyridines were synthesized and tested as inhibitors of TNF-α production. The most potent compounds were N-(4,6-dimethyl-pyridin-2-yl)tetrafluorophthalimide (8, 40% inhibition at 10 μM), N-(3-methylpyridinyl)-5-fluorophthalimide (12, 48%) and N-(3-methylpyridinyl)tetrafluorophthalimide (13, 68%). The analogues without (tetra)fluorine substitution on the aromatic ring were less active inhibitors.
