- Lewis acid-catalyzed generation of C-C and C-N bonds on π-deficient heterocyclic substrates
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Focused microwave irradiation of a series of halogenated nitrogen heterocycles and different kinds of nucleophiles in the presence of a catalytic amount of indium trichloride leads to the efficient and completely regioselective generation of aromatic C-C and C-N bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work-up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation and amination reactions on π-deficient heterocyclic substrates.
- Staderini, Matteo,Bolognesi, Maria Laura,Menndez, J. Carlos
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supporting information
p. 185 - 195
(2015/01/30)
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- Synthesis of monomeric and dimeric acridine compounds as potential therapeutics in Alzheimer and prion diseases
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Starting from substituted 9-chloroacridines, a series of quinacrine and spacered dimeric acridine compounds was prepared. Their ability to interrupt the protein association of prion- and Alzheimer-specific proteins and Ab peptides was explored using a fast screening system based on FACS analysis. The bis-acridines displayed a higher activity than the corresponding monomers. Among these derivatives, best results were obtained with the 2,4-dimethoxy-6-nitro compound 7h for Aβ-peptides and the 2-methoxy-6-nitro compound 7f for PrP.
- Csuk, Rene,Barthel, Alexander,Raschke, Christian,Kluge, Ralph,Stroehl, Dieter,Trieschmann, Lothar,Boehm, Gerald
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experimental part
p. 699 - 709
(2010/06/19)
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- Pharmaceutical compounds for treating copd
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Use of an MPO inhibitor for the treatment of COPD.
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- Inhibition of Trypanosoma cruzi trypanothione reductase by acridines: Kinetic studies and structure-activity relationships
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Series of 9-amino and 9-thioacridines have been synthesized and studied as inhibitors of trypanothione reductase (TR) from Trypanosoma cruzi, the causative agent of Chagas' disease. The compounds are structural analogues of the acridine drug mepacrine (quinacrine), which is a competitive inhibitor of the parasite enzyme, but not of human glutathione reductase, the closest related host enzyme. The 9-aminoacridines yielded apparent K(i) values for competitive inhibition between 5 and 43 μM. The most effective inhibitors were those with the methoxy and chlorine substituents of mepacrine and NH2 or NHCH(CH3)(CH2)4N(Et)2 at C9. Detailed kinetic analyses revealed that in the case of 9- aminoacridines more than one inhibitor molecule can bind to the enzyme. In contrast, the 9-thioacridine derivatives inhibit TR with mixed-type kinetics. The kinetic data are discussed in light of the three-dimensional structure of the TR-mepacrine complex. The conclusion that structurally very similar acridine compounds can give rise to completely different inhibition patterns renders modelling studies and quantitative structure-activity relationships difficult.
- Bonse, Susanne,Santelli-Rouvier, Christiane,Barbe, Jacques,Krauth-Siegel, R. Luise
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p. 5448 - 5454
(2007/10/03)
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- Method for inactivating non-enveloped viruses using a viricide-potentiating agent with a photoactivatible virucide
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Method for inactivating non-enveloped viruses using a viricide-potentiating agent. In a preferred embodiment, the method may be used to inactivate non-enveloped viruses present within a sample of whole blood or a blood product and comprises (a) adding to the blood sample a photoactivatable viricide, such as a psoralen, hypericin, methylene blue, toluidine blue or the like, which, when activated, is effective in inactivating enveloped viruses; (b) adding to the blood sample a viricide-potentiating chemical agent that increases the sensitivity of non-enveloped viruses to the activated viricide; and (c) activating the photoactivatable viricide. Preferably, the viricide-potentiating chemical agent includes a first moiety which possesses an affinity for a component of the non-enveloped virus and a second moiety which includes a lipid tail, the first and second moieties being structurally interrelated so that, when the first moiety becomes associated with a component of the non-enveloped virus, the second moiety penetrates or at least partially surrounds the viral capsid of the non-enveloped virus. Examples of the chemical agent include cationic lipopolyamines, such as dioctadecylamidoglycylspermine.
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