17624-26-9Relevant articles and documents
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Paquette
, p. 2870 (1962)
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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.
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).