18470-33-2Relevant academic research and scientific papers
Electrochemical: N -demethylation of tropane alkaloids
Alipour Najmi, Ali,Bischoff, Rainer,Dekker, Frank J.,Permentier, Hjalmar P.,Xiao, Zhangping
, p. 6455 - 6463 (2020/11/09)
A practical, efficient, and selective electrochemical N-demethylation method of tropane alkaloids to their nortropane derivatives is described. Nortropanes, such as noratropine and norscopolamine, are important intermediates for the semi-synthesis of the medicines ipratropium or oxitropium bromide, respectively. Synthesis was performed in a simple home-made electrochemical batch cell using a porous glassy carbon electrode. The reaction proceeds at room temperature in one step in a mixture of ethanol or methanol and water. The method avoids hazardous oxidizing agents such as H2O2 or m-chloroperbenzoic acid (m-CPBA), toxic solvents such as chloroform, as well as metal-based catalysts. Various key parameters were investigated in electrochemical batch or flow cells, and the optimized conditions were used in batch and flow-cells at gram scale to synthesize noratropine in high yield and purity using a convenient liquid-liquid extraction method without any need for chromatographic purification. Mechanistic studies showed that the electrochemical N-demethylation proceeds by the formation of an iminium intermediate which is converted by water as the nucleophile. The optimized method was further applied to scopolamine, cocaine, benzatropine, homatropine and tropacocaine, showing that this is a generic way of N-demethylating tropane alkaloids to synthesize valuable precursors for pharmaceutical products.
Utility of iron nanoparticles and a solution-phase iron species for the: N-demethylation of alkaloids
Awalt, Jon Kyle,Lam, Raymond,Kellam, Barrie,Graham, Bim,Scammells, Peter J.,Singer, Robert D.
, p. 2587 - 2594 (2017/07/17)
The N-demethylation of selected N-methylalkaloids using a modified Polonovski reaction can be accomplished using a novel green methodology employing nanoscale zero-valent iron, nZVI, in isopropanol. Use of nZVI promotes a much faster conversion to N-demethylated products due to much higher surface area on the metal surface as shown by SEM analysis. Rates of conversion can be further enhanced using catalytic quantities of the solubilised iron(0) species triiron dodecacarbonyl, Fe3(CO)12.
CHROMEN-2-ONE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
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Page/Page column 14, (2012/01/14)
The present applications discloses novel 8-aza-bicyclo[3.2.1]oct-3-yloxy)-chromen-2-one derivatives and their use as monoamine neurotransmitter re-uptake inhibitors. In other aspects the applications discloses the use of these compounds in a method for th
NOVEL COMPOUNDS
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, (2012/01/14)
The present applications discloses novel 8-aza-bicyclo[3.2.1]oct-3-yloxy)chromen-2-one derivatives and their use as monoamine neurotransmitter re-uptake inhibitors. In other aspects the applications discloses the use of these compounds in a method for the
Structure-based design, synthesis and structure-activity relationships of dibenzosuberyl- and benzoate-substituted tropines as ligands for acetylcholine-binding protein
Edink, Ewald,Akdemir, Atilla,Jansen, Chimed,Elk, René Van,Zuiderveld, Obbe,De Kanter, Frans J.J.,Van Muijlwijk-Koezen, Jacqueline E.,Smit, August B.,Leurs, Rob,De Esch, Iwan J.P.
, p. 1448 - 1454 (2012/04/04)
Using structure-based optimization procedures on in silico hits, dibenzosuberyl- and benzoate substituted tropines were designed as ligands for acetylcholine-binding protein (AChBP). This protein is a homolog to the ligand binding domain of the nicotinic acetylcholine receptor (nAChR). Distinct SAR is observed between two AChBP species variants and between the α7 and α4β2 nAChR subtype. The AChBP species differences are indicative of a difference in accessibility of a ligand-inducible subpocket. Hereby, we have identified a region that can be scrutinized to achieve selectivity for nicotinic receptor subtypes.
CHROMEN-2-ONE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
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, (2011/08/21)
The present application discloses novel 8-aza-bicyclo[3.2.1]oct-3-yloxy)-chromen- 2-one derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the application discloses the use of these compounds, a method for therapy and to pharmaceutical compositions comprising these compounds.
CHROMEN-2-ONE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
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, (2010/12/17)
The present applications discloses novel 8-aza-bicyclo[3.2.1]oct-3-yloxy)- chromen-2-one derivatives and their use as monoamine neurotransmitter re-uptake inhibitors. In other aspects the applications discloses the use of these compounds in a method for t
NOVEL BENZOOXAZOL- AND BENZOOXATHIOL-2-ONE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
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Page/Page column 11, (2009/04/25)
This invention relates to novel benzooxazol- and benzooxathiol-2-one derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.
NOVEL PHENOXAZIN-3-ONE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
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Page/Page column 10, (2009/04/25)
This invention relates to novel phenoxazin-3-one derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.
NOVEL CHROMEN-2-ONE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
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, (2008/12/06)
This invention relates to novel chromen-2-one derivatives of Formula (I) useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical composit
