33558-16-6Relevant academic research and scientific papers
N-(Anilinoethyl)amide Melatonergic Ligands with Improved Water Solubility and Metabolic Stability
Ferlenghi, Francesca,Mari, Michele,Gobbi, Gabriella,Elisi, Gian Marco,Mor, Marco,Rivara, Silvia,Vacondio, Federica,Bartolucci, Silvia,Bedini, Annalida,Fanini, Fabiola,Spadoni, Gilberto
, p. 3071 - 3082 (2021)
The MT2-selective melatonin receptor ligand UCM765 (N-(2-((3-methoxyphenyl)(phenyl)amino)ethyl)acetamide), showed interesting sleep inducing, analgesic and anxiolytic properties in rodents, but suffers from low water solubility and modest metabolic stability. To overcome these limitations, different strategies were investigated, including modification of metabolically liable sites, introduction of hydrophilic substituents and design of more basic derivatives. Thermodynamic solubility, microsomal stability and lipophilicity of new compounds were experimentally evaluated, together with their MT1 and MT2 binding affinities. Introduction of a m-hydroxymethyl substituent on the phenyl ring of UCM765 and replacement of the replacement of the N,N-diphenyl-amino scaffold with a N-methyl-N-phenyl-amino one led to highly soluble compounds with good microsomal stability and receptor binding affinity. Docking studies into the receptor crystal structure provided a rationale for their binding affinity. Pharmacokinetic characterization in rats highlighted higher plasma concentrations for the N-methyl-N-phenyl-amino derivative, consistent with its improved microsomal stability and makes this compound worthy of consideration for further pharmacological investigation.
Selective copper-promoted cross-coupling of aromatic amines with alkyl boronic acids
Larrosa, Marta,Guerrero, César,Rodríguez, Ramón,Cruces, Jacobo
supporting information; experimental part, p. 2101 - 2105 (2010/10/03)
A simple copper-promoted N-monoalkylation of anilines that utilizes alkyl boronic acids as the alkylating partner is presented. The reaction is carried out in refluxing dioxane, and it allows a number of structurally and electronically diverse anilines to be functionalized in a single step. A broad study was carried out to demonstrate the utility of this new methodology for the preparation of phenethylanilines.
Amination of aromatic olefins with anilines: A new domino synthesis of quinolines
Beller, Matthias,Thiel, Oliver R.,Trauthwein, Harald,Hartung, Christian G.
, p. 2513 - 2522 (2007/10/03)
A new catalytic amination of aromatic olefins with anilines is presented. In a domino reaction, substituted quinoline derivatives are obtained in the presence of cationic rhodium complexes, such as [Rh(cod)2]BF4, and PPh3. Ethylbenzene is formed as a by-product in this new oxidative reaction. The first transition metal catalyzed anti-Markovnikov hydroamination of styrene with anilines occurs as a side reaction. Mechanistic investigations strongly support the regioselective oxidative amination of styrene as the key reaction step.
