4646-55-3Relevant academic research and scientific papers
Development of a general non-noble metal catalyst for the benign amination of alcohols with amines and ammonia
Cui, Xinjiang,Dai, Xingchao,Deng, Youquan,Shi, Feng
supporting information, p. 3665 - 3675 (2013/03/29)
The N-alkylation of amines or ammonia with alcohols is a valuable route for the synthesis of N-alkyl amines. However, as a potentially clean and economic choice for N-alkyl amine synthesis, non-noble metal catalysts with high activity and good selectivity are rarely reported. Normally, they are severely limited due to low activity and poor generality. Herein, a simple NiCuFeOx catalyst was designed and prepared for the N-alkylation of ammonia or amines with alcohol or primary amines. N-alkyl amines with various structures were successfully synthesized in moderate to excellent yields in the absence of organic ligands and bases. Typically, primary amines could be efficiently transformed into secondary amines and N-heterocyclic compounds, and secondary amines could be N-alkylated to synthesize tertiary amines. Note that primary and secondary amines could be produced through a one-pot reaction of ammonia and alcohols. In addition to excellent catalytic performance, the catalyst itself possesses outstanding superiority, that is, it is air and moisture stable. Moreover, the magnetic property of this catalyst makes it easily separable from the reaction mixture and it could be recovered and reused for several runs without obvious deactivation. Copyright
An improved asymmetric synthetic route to a novel triple uptake inhibitor antidepressant (2S,4R,5R)-2-benzhydryl-5-((4-methoxybenzyl)amino)tetrahydro-2H- pyran-4-ol (D-142)
Gopishetty, Bhaskar,Gogoi, Sanjib,Dutta, Aloke K.
experimental part, p. 1081 - 1086 (2011/10/04)
Triple monoamine reuptake inhibitors have been implicated in the development of a new generation of antidepressants with higher efficacy than the currently existing therapies. In this paper, we have developed an alternative efficient synthetic route for triple monoamine reuptake inhibitor D-142 in 18.5% overall yield in 11 steps starting from diphenylmethane. D-142 was developed by us recently. The key step of the present synthetic strategy is the preferential formation of a bromohydrin from olefin via a cis-bromonium intermediate, which introduced significant efficiency in the overall synthesis. Furthermore, we have developed an efficient way to recycle the optically active intermediate diol back to the desired chiral epoxide.
Synthesis, structure-affinity relationships, and modeling of AMDA analogs at 5-HT2A and H1 receptors: Structural factors contributing to selectivity
Shah, Jitesh R.,Mosier, Philip D.,Roth, Bryan L.,Kellogg, Glen E.,Westkaemper, Richard B.
experimental part, p. 6496 - 6504 (2009/12/06)
Histamine H1 and serotonin 5-HT2A receptors present in the CNS have been implicated in various neuropsychiatric disorders. 9-Aminomethyl-9,10-dihydroanthracene (AMDA), a conformationally constrained diarylalkyl amine derivative, has affinity for both of these receptors. A structure-affinity relationship (SAFIR) study was carried out studying the effects of N-methylation, varying the linker chain length and constraint of the aromatic rings on the binding affinities of the compounds with the 5-HT2A and H1 receptors. Homology modeling of the 5-HT2A and H1 receptors suggests that AMDA and its analogs, the parent of which is a 5-HT2A antagonist, can bind in a fashion analogous to that of classical H1 antagonists whose ring systems are oriented toward the fifth and sixth transmembrane helices. The modeled orientation of the ligands are consistent with the reported site-directed mutagenesis data for 5-HT2A and H1 receptors and provide a potential explanation for the selectivity of ligands acting at both receptors.
Hydroaminomethylation with novel Rhodium-Carbene complexes: An efficient catalytic approach to pharmaceuticals
Ahmed, Moballigh,Buch, Cathleen,Routaboul, Lucie,Jackstell, Ralf,Klein, Holger,Spannenberg, Anke,Beller, Matthias
, p. 1594 - 1601 (2008/02/04)
Starting from [{Rh(cod)Cl}2] and 1,3-dimesitylimidazole-2- ylidenes the novel [RhCl(cod)(carbene)] complexes 1-5 have been synthesized, characterized, and tested in the hydroaminomethylation of aromatic olefins. The influence of different ligands and reaction parameters on the catalytic activity was investigated in detail applying 1,1-diphenylethylene and piperidine as a model system. The scope and limitations of the novel catalysts is shown in the preparation of 16 biologically active 1-amino-3,3-diarylpropenes. In general, high chemo- and regioselectivity as well as good yields of the desired products were achieved.
Synthesis, pharmacological and biophysical characterization, and membrane-interaction QSAR analysis of cationic amphiphilic model compounds
Klein, Christian D. P.,Klingmüller, Martin,Schellinski, Christiane,Landmann, Silke,Hauschild, Stefanie,Heber, Dieter,Mohr, Klaus,Hopfinger
, p. 3874 - 3888 (2007/10/03)
Cationic amphiphilic drugs have a propensity to interact with biological interphases. This study was designed to gain more insight into the molecular properties of catamphiphilic drugs which govern this type of interaction. A series of phenylpropylamine model compounds were synthesized in which modifications were incorporated at the aromatic part of the molecule. The replacement of 45Ca2+ from phosphatidylserine monolayers served to monitor drug binding to the phospholipid. The influence on the phase- transition temperature of liposomes of dipalmitoylphosphatidic acid was measured to assess the perturbing action of the drugs on the structural organization of phospholipid assemblies. The antiarrhythmic activity of the compounds was determined in Langendorff preparations of guinea pig hearts to assess the membrane-stabilizing action. Quantitative structure-activity relationship (QSAR) models for these endpoints were developed using both intra- and intermolecular QSAR descriptors. Intermolecular membrane- interaction descriptors were derived from molecular dynamics simulations of the compounds in a model phospholipid monolayer. QSAR models were derived for all endpoints using partial least-squares regression (PLS) and a genetic algorithm tool, the genetic function approximation (GFA). Membrane- interaction descriptors appear to be of a particular importance in explaining the influence of the compounds on the phase-transition temperature of DPPA liposomes, while the other endpoints can be adequately modeled by intramolecular descriptors. The calcium-displacing activity at phosphatidylserine monolayers is governed by the electrostatic properties of the compounds. Measures of lipophilicity and molecular size are of particular importance for antiarrhythmic activity. Possible improvements to both the molecular modeling and the applied computational protocol of membrane-solute systems are identified and discussed.
Reductive electrophilic substitution of diarylmethyl methyl ethers: Synthetic applications
Azzena,Melloni,Fenude,Fina,Marchetti,Sechi
, p. 591 - 599 (2007/10/02)
The reductive cleavage of diarylmethyl methyl ethers with Li metal in THF led to quantitative formation of the corresponding diarylmethyl anions. Quenching with electrophiles afforded substituted diarylmethanes in good to excellent yields.
